Most of the outfits I build start with a shirt, because a woven collar and a button front can go to an office, a lunch or a Saturday errand with very little change. Crisp poplin shirts hold their shape and look sharp, while linen, chambray, satin and soft cotton each move and wrinkle in their own way. Below are 50 shirts with the bottoms, shoes and bags I'd actually pair with them, plus notes on who each one suits and where it tends to go wrong. Read the fit section first; a shirt that pulls at the bust spoils every outfit on this list.
The Button Gap and the Shoulder Line
Most shirts fail in the same two places, the shoulders and the bust. I check both in the fitting room before I even look at the color, because no styling trick fixes a shirt that pulls.
- Shoulder seam: it should sit on the edge of your shoulder bone. If it slides down your arm, the shirt is cut oversized, which is fine only when that's the look you want.
- Bust: button it fully and reach forward as if you're holding a steering wheel. If the placket opens into little gaps between buttons, the shirt is too tight there.
- Sleeves: with your arms relaxed, the cuff should land at the wrist bone. Too long and it bunches; you can roll it, but a shirt you always have to roll gets worn less.
- Back: raise both arms. If the hem pops out of your waistband straight away, the body is too short for tucked outfits.
- Fabric: hold a single layer up to the light. Thin white or pale cotton will show your bra, so plan a skin-tone layer before you buy.
When the shoulders fit and the bust doesn't, going up a size usually leaves the shoulders hanging off you. In that case I look for a shirt with bust darts, a little stretch in the poplin or a hidden placket, and I let a tailor take in the waist afterward. Taking in a side seam is simple; adding room across the chest isn't really possible.
1. White Button-Down Shirt With Tailored Trousers
Before anything else I check the shoulder seam: it should land on the edge of your shoulder bone, and the buttons across the bust should lie flat with no gaps when you reach forward. Once that's right, a full tuck into high-rise black, navy or camel trousers does most of the work. Straight or gently wide legs both suit it, with loafers, pointed flats or a low block heel and a structured tote. To take it down a notch, roll the sleeves to just below the elbow and open the top button. Petite frames do best with ankle-length trousers, while tall women can carry a longer inseam and a slightly oversized shirt.
2. Striped Shirt With Straight-Leg Jeans
Stripes are forgiving, and a blue-and-white button-up with mid or dark straight-leg jeans is the outfit I reach for when someone says they have nothing to wear. Vertical stripes draw the eye up and down, so this shirt lengthens the torso more than a solid one. I like a relaxed cut you can half-tuck or wear open over a fitted tank. Curved side seams give shape without tucking, and a hem below the hipbone covers the hips if you'd rather leave it out. White sneakers or loafers, a tan crossbody, small hoops and a slim watch are all it needs.
3. Linen Shirt With High-Waisted Shorts
For a hot day, linen is the coolest shirt fabric I know, because the flax fiber lets air through and dries quickly. It also creases the minute you sit down. I accept that and steam it lightly rather than pressing it flat, since the texture suits shorts anyway. A white, sage or pale blue linen button-down with high-waisted tailored shorts, a loose front tuck and flat leather sandals is the whole outfit. Pick shorts with a wider leg opening so they don't ride up the thighs, add a breathable camisole if the linen is thin, and swap to Bermuda shorts if you want more length.
4. Satin Shirt With Midi Skirt
Light bouncing off satin is what makes it look dressy, and it's also why it shows every crease, sweat mark and water spot. I pair a fluid champagne, navy or burgundy satin shirt with a matte midi skirt so the shine has something quiet beside it. A bias-cut skirt moves; a pleated or A-line one gives more structure and coverage. Tuck it cleanly, then add pointed slingbacks or a low sandal heel, a compact shoulder bag and fine metal jewelry. If you'd rather soften the stomach or bust, go darker and choose a relaxed cut that skims. Washable satin is the practical pick for dinners, celebrations and dressier daytime plans.
5. Denim Shirt With Black Maxi Skirt
Black and denim make one of the easiest contrasts to wear because neither piece fights the other. Tuck a medium-wash denim shirt into a flowing black maxi skirt; the rule I follow is fitted shirt with full skirt, relaxed shirt with a straighter column. Thick denim bunches at the waistband, so a softer, chambray-weight shirt tucks far more smoothly. A structured belt links top and bottom, with ankle boots in cool weather and flat sandals when it warms up. For more coverage and a lighter neckline, wear the shirt partly unbuttoned over a fitted black tank, then add a plain shoulder bag and silver jewelry.
6. Chambray Shirt With White Jeans
Woven with a colored warp and a white weft, chambray looks like denim but is far lighter, which makes it a good partner for white jeans from spring into early fall. Choose a soft shirt with minimal fading and front-tuck it into straight or gently wide white jeans. Wear nude underwear rather than white, because white shows through white denim more than a skin tone does. Tan loafers, a cognac belt and a matching crossbody warm up the pale palette. If bright white feels harsh, ecru jeans are kinder. Curvy women usually prefer heavier stretch denim, and tall women can go full-length with a slightly oversized shirt.
7. Oversized Shirt With Biker Shorts
The test I use here is the back view. An oversized poplin shirt over mid-thigh biker shorts looks deliberate only if the shirt covers enough behind you, so check a mirror before you leave. Layer it over a fitted tank and leave it open, or button it so just a strip of shorts shows. A structured collar keeps all that volume from reading as a nightshirt. Chunky white sneakers, crew socks, a crossbody and sunglasses suit errands, travel days and coffee runs; skip anything formal.
8. Cropped Shirt With Wide-Leg Pants
On a cropped shirt, the hem should land at the waistband or a finger's width above it, not halfway up the ribs, unless you want midriff on show. A boxy cotton poplin crop over high-rise wide-leg trousers in linen, crepe or light twill gives clean proportions with almost no effort. I keep the colors tonal, white with cream or pale blue with navy. Wide hems need a platform sandal or a substantial sneaker under them, plus a small bag so accessories don't crowd the shape. Petite women wear this well when the trousers have a flat front, a high waist and a hem that almost touches the shoe, and a fitted camisole adds coverage.
9. Oxford Shirt With Pleated Midi Skirt
The slight basketweave texture of Oxford cloth makes it more relaxed than poplin, so it sits comfortably with the softness of a pleated midi skirt. Choose pale blue, white or a fine stripe and tuck it into narrow, fluid pleats in navy, camel or olive. Volume is the thing to watch: a full skirt needs a closer-fitting Oxford, or the waist disappears under extra fabric. Loafers make it preppy; pointed flats make it lighter. Keep the sleeves down for the office, roll them to the forearm on weekends, and add a slim belt only if the waistband needs it.
10. Black Button-Down Shirt With Cream Pants
Black with cream is softer than black with white, and I find it easier on most complexions. A fluid black button-down over high-rise cream trousers, fully tucked or front-tucked, is the outfit. Light trousers show pocket bags and lining lines, so I look for a heavier fabric and a smooth flat front before buying. Open the collar into a V to lengthen the neck and stop the dark top from feeling heavy near the face. Black loafers or slingbacks, a structured black bag and gold jewelry for warmth carry it through offices, conferences and lunches.
11. Poplin Shirt With Cargo Pants
Crisp poplin is what keeps cargo pants from looking like workwear. Pair a white, blue or soft pink button-up with high-rise cargos in olive, khaki or black, and keep the shirt fitted or only slightly relaxed, since the pockets already add bulk below. Tuck it in and wear sleek sneakers or simple leather sandals; very chunky shoes only work with very wide legs. If your hips are fuller, look for flatter pockets set a little higher on the thigh. I roll the sleeves twice, add a small shoulder bag and hoops, and leave it there.
12. Silk Shirt With Pencil Skirt
Real silk breathes and drapes, but it water-spots and shows perspiration, so I keep it for the office and dinners rather than hot commutes. A softly draped ivory, teal or navy silk shirt tucked into a knee-length or midi pencil skirt gives the classic tailored line. Size for the bust: if the fabric strains between buttons, it won't fall smoothly however good the silk is. Silk can be sheer, so a smooth camisole underneath is worth it. A stretch fabric and a back slit fix most of the restriction of a traditional pencil skirt; finish with pointed pumps or slingbacks and a structured work bag.
13. Bow-Neck Shirt With Tailored Pants
I never pull the tie of a bow-neck shirt tight against the throat; a loose knot sitting slightly low looks current and is far more comfortable over a long day. Choose ivory, blush, navy or a quiet print, and pair it with straight or gently flared trousers in a matching neutral. A partial or full tuck keeps the bow and the extra fabric from swamping the upper body. Skip necklaces and wear earrings instead. With a fuller bust, a narrower tie and an open V neckline work better, and under a blazer the bow should sit above the lapels rather than being crushed by them.
14. Ruffle Shirt With Straight-Leg Jeans
Keep the jeans plain and ruffles look current. Choose a white, black or muted floral shirt with controlled ruffles at the collar, cuffs or placket rather than tiers of volume, and tuck it into clean high-rise straight-leg denim. Broad shoulders are the main thing I plan around: vertical ruffles down the placket narrow the frame, while ruffles across the shoulder widen it further. Loafers or ballet flats and a structured leather bag give it some contrast. It's a good choice for casual offices and weekend lunches when a plain shirt feels too plain.
15. Eyelet Shirt With Denim Maxi Skirt
Cotton eyelet has small holes finished with stitching, so it's breathable and textured but rarely opaque. Look for a shirt with embroidered cutwork and either a lining or a smooth camisole underneath. A fitted waist-length style goes with an A-line denim maxi; a relaxed eyelet button-up suits a straighter one. Tan sandals or white sneakers and a woven shoulder bag are all I'd add, since the fabric already carries the detail. If a full maxi feels like a lot of skirt, choose a front slit or an ankle-skimming hem, which also helps on market days and vacations.
16. Gingham Shirt With Chino Pants
Check size changes everything with gingham. A small check reads almost as a solid from across a room, so it's the version I suggest for professional settings, while a large check is louder and more casual. Pair navy, green or light blue gingham with slim-straight or relaxed chinos in khaki, cream or navy. Tuck it for polish, or leave it out only if the shirt has a short curved hem. Make sure the buttons sit flat across the bust, because a check pattern makes any pulling very obvious. Loafers or canvas sneakers, a simple belt and a crossbody in the same color family finish it.
17. Plaid Shirt With Faux Leather Pants
Plaid softens the hard shine of faux leather, provided the plaid contains a color from the pants, usually black, charcoal or deep green. A brushed flannel keeps it casual; a lighter viscose or cotton plaid looks more polished. Tuck the front into high-rise straight-leg pants and let the back hang loose. The combination I steer people away from is an extremely oversized shirt with very loose leather pants, because both pieces are heavy and the shape collapses. For less contrast, try brown faux leather with a plaid that has warm beige or rust in it, plus ankle boots and a small black bag.
18. Flannel Shirt With Leggings And Boots
Leggings show everything through thin fabric, so before the shirt I check the leggings: bend over in good light, make sure they stay opaque, and choose a wide waistband. Then a longline plaid flannel that covers the hips, worn over a fitted tank or tee, makes an easy cool-morning outfit. Flat ankle boots or lace-up weather boots give it structure, and a tote handles errands. For more shape, button the shirt and add a slim belt or a fitted vest. Brushed flannel in navy, forest green or burgundy gets reworn all through fall and winter.
19. Utility Shirt With Cargo Skirt
Two pieces covered in pockets can look like a uniform, so I tuck the utility shirt to break the boxy line at the waist. Choose khaki, olive, stone or charcoal with chest pockets and a clean collar, and match it to a midi cargo skirt in the same or a close neutral. If both pieces are oversized, a belt or a straight skirt rescues the shape. Petite women do better with fewer, flatter pockets, while taller women can carry longer hems and more visible detailing. Flat sandals or low sneakers and a simple crossbody keep the practical feel.
20. Camp Collar Shirt With Linen Pants
For a relaxed vacation feel, a camp collar shirt is my first pick. Its collar lies flat and open with no collar stand, and that open V breaks up the chest, which helps a fuller bust or broader upper body. Choose short sleeves in a solid, a subtle stripe or a botanical print and tuck it into high-rise wide-leg linen pants, or wear it open over a fitted tank. Pale linen pants are often see-through, so look for a partial lining. Tonal pairs like cream with sand look the most put-together; flat slides, a straw tote and a pendant that sits inside the collar are enough.
21. Polo Shirt With Tailored Shorts
Swap gym shorts for tailored pleated shorts and a polo stops looking like sportswear. I choose fine cotton pique or a light knit polo in navy, cream or a stripe, tucked into high-rise shorts with a moderate inseam. Pique is textured and breathes well, though cotton can shrink in a hot wash. Leave one or two buttons open, then add loafers or fisherman sandals and a structured mini tote rather than anything athletic. Fuller arms are happier in elbow-length sleeves, and petite women should look for a smaller collar so it doesn't overwhelm the face.
22. Rugby Shirt With Relaxed Jeans
The heavy cotton jersey and sturdy woven collar of a rugby shirt hold their shape and never need ironing, but that weight also makes them bulky to tuck. A small front tuck into relaxed straight or gently baggy jeans is as far as I go. Keep the denim clean rather than distressed, and add retro sneakers or loafers with a compact leather shoulder bag so it doesn't look like team kit. Wide horizontal stripes widen the chest; if that bothers you, choose narrower bands or a solid body with a contrast collar. Pushing the sleeves up a little lightens the whole shape.
23. Tunic Shirt With Leggings
Mid-thigh is where a tunic should stop, and it should skim the body; any wider and it turns into a tent over leggings. Side vents, a split hem or a curved shirttail let it move when you walk and sit. Wear it with opaque black, navy or chocolate leggings and loafers, sneakers or ankle boots. Curvy women usually prefer a fluid fabric over stiff poplin, which stands away from the body. Petite women should go slightly shorter so more leg shows. A crossbody strap worn near the natural waist adds a hint of definition without a belt, and with a printed tunic I keep jewelry to one long pendant at most.
24. Peplum Shirt With Ankle Pants
With a peplum shirt, everything depends on where the flare starts. It should begin at your natural waist; if it starts right under the bust, it adds volume to the stomach instead of shaping it. Pair it with slim-straight ankle trousers in black, navy or cream, and add pointed flats or a low block heel to lengthen the leg below the cropped hem. Skip a wide belt, because the peplum is already doing that job. Puff sleeves on a peplum should stay modest, or you end up with volume at the shoulders and hips at once. A solid shirt with clean seams is the quieter option for offices and presentations.
25. Wrap Shirt With A-Line Midi Skirt
You get a V neckline and a defined waist in one piece from a wrap shirt, but it can gape open when you move. I secure the overlap with a small safety pin on the inside or wear a camisole underneath. Pair it with an A-line midi that flows away from the hips without a bulky waistband, so the ties lie flat. A solid wrap with a printed skirt, or a quiet print with navy, black or cream, keeps the balance. Fuller busts need adjustable ties and enough fabric across the chest. Low heels or slingback flats and a small shoulder bag keep it from looking too formal.
26. Puff-Sleeve Shirt With Dark Jeans
Dark-wash jeans are the right partner for a puff-sleeve shirt because they're plain enough to let the sleeves be the point. I look for volume concentrated at the shoulder with a narrow cuff, which gives shape without widening the whole upper body. Tuck it into high-rise straight or slim-flare indigo jeans and add pointed flats, heeled ankle boots or loafers. If your shoulders are broad, choose soft gathered sleeves rather than padded or stiffened ones. Skip a big necklace; studs and a structured bag are enough, and a smooth, fitted torso keeps the sleeves in proportion.
27. Balloon-Sleeve Shirt With Slip Skirt
Full through the arm and gathered at the cuff, a balloon sleeve looks best against something smooth like a satin or matte crepe slip skirt. Tuck a cotton or light woven blouse in cleanly so the sleeves are the only volume. One piece stays neutral if the other is printed or brightly colored; two loud pieces start to look like a costume. Push the sleeves toward the elbow to shrink them visually. Slingbacks or minimal sandals and a compact bag suit creative offices, dinners and gallery evenings, and the arms and legs stay covered the whole time.
28. Collarless Shirt With Tailored Culottes
Without a collar, the neckline is bare, so this is where I add a short pendant or sculptural earrings. A button-front or concealed-placket collarless shirt in ivory, black or blue tucks neatly into high-rise culottes that end between the lower calf and the ankle. Culottes cut across the calf, so pointed flats, sleek loafers or low heels matter here more than usual. Petite women should choose a narrower leg and a slightly shorter hem. With a long torso, a higher rise and a shirt with some shoulder structure even out the proportions.
29. Mandarin Collar Shirt With Wide-Leg Pants
The short standing band of a mandarin collar has no fold-over, so it reads cleaner than a pointed collar. Pair a white, black or soft blue mandarin shirt with high-waisted wide-leg pants, in fluid fabric for a soft monochrome look or crisp cotton for something sharper. Tuck it in fully to keep your outline against the wide legs. If the band feels tight, leave the top button open; for a fuller bust, a slightly deeper placket opens up the chest. Low block heels or leather sandals, a structured bag and geometric earrings suit the neat line from the office to travel days.
30. Sheer Shirt With Camisole And Trousers
With a sheer shirt, the camisole is part of the outfit, not underwear, so I choose it as deliberately as the trousers. Put a smooth camisole in a matching or contrasting color under a light black, white or printed shirt, and tuck both into tailored high-rise trousers. The cami must be long enough to stay tucked when you sit, and wide straps add coverage. Tonal layers look quiet; black under a pale shirt is far more graphic. Always check it in daylight before leaving, because sheer fabric is much more transparent outdoors than under fitting-room lights.
31. Lace-Trim Shirt With Tailored Jeans
Lace looks refined against clean denim and fussy against distressed denim, so I keep the jeans dark and straight or trouser-cut. Choose a shirt with lace at the collar, cuffs or placket, tuck it in and add a slim leather belt if needed. Open lace panels need a camisole underneath, and with a high lace collar I skip the necklace altogether. Ballet flats or slingbacks, a structured bag and small earrings make this a step up from an everyday shirt without tipping into occasion wear. Lace snags on hook-and-loop fastenings and rough bag straps, so I wash it in a mesh bag.
32. Floral Shirt With Solid Wide-Leg Pants
My method for a floral shirt is simple: find the quietest neutral in the print, often navy, cream or olive, and make the wide-leg pants that color. Tuck it into a high waistband so the print has a frame. A medium-scale floral is the easiest to coordinate and looks the most current. Neutral shoes and a bag in one of the accent colors pull it together. Curvy figures look good in a fluid fabric that moves over the body, petite women in a smaller print, and in both cases the shirt carries the decoration, so jewelry stays small.
33. Animal-Print Shirt With Black Pants
Plain black around it is what makes animal print look expensive. Wear a leopard, zebra or abstract animal-print shirt with tailored black straight-leg pants, and pick a print with a limited palette so it reads as a pattern rather than noise. A full tuck looks polished; a small front tuck relaxes it. Gold or silver hoops are enough, with loafers, ankle boots or pointed heels. If an all-over print feels loud, wear the shirt open over a black tank so less of it shows. It goes from a creative office to dinner with no change.
34. Color-Block Shirt With Dark Denim
In a color-block shirt, darker panels recede and lighter ones advance, so I look for the darker color where you want less attention. Two or three coordinated colors are plenty. Pair it with clean indigo straight-leg or bootcut jeans, tucked into a high rise or worn with a short hem that ends near the hipbone. Vertical and diagonal blocks lengthen the torso; very wide horizontal bands broaden it. Choose a bag in one of the shirt's quieter colors and limit jewelry to studs, with loafers or ankle boots underneath.
35. Tie-Front Shirt With Maxi Skirt
The knot decides this outfit. It should meet the maxi skirt's waistband; a strip of skin between them looks accidental unless you planned it. With a short torso, tie it a little lower, and with a long waist choose a higher waistband instead. A fitted tank underneath lets you adjust the knot without worrying about coverage. Keep the knot small, since big ones add bulk at the center. Cotton, linen or light viscose with a straight or slightly A-line skirt works best, with flat sandals or espadrilles and a woven bag in summer.
36. Sleeveless Button-Down Shirt With Bermuda Shorts
The armholes matter most on a sleeveless shirt. They should sit close enough that your bra doesn't show when you lift an arm, and wide shoulder panels hide the straps. Tuck it into high-rise Bermuda shorts that end near or just above the knee, in cream, navy, khaki or black. A belt makes the longer shorts look intended, and a softly draped shirt is the alternative if stiff cotton feels severe. Loafers or flat sandals, a tote, sunglasses and small earrings suit sightseeing, casual offices and daytime plans.
37. Short-Sleeve Shirt With Cropped Trousers
For weeks when mornings are cool and afternoons aren't, I reach for a short-sleeve shirt with cropped trousers. Look for a neat collar and sleeves that end around the middle of the upper arm, or elbow-length if you want more coverage. Pair it with ankle-length tailored pants in black, navy, olive or tan. The balance rule is simple: boxy shirt, narrower trousers; fitted shirt, slightly wider ones. Pointed flats or loafers lengthen the leg below the cropped hem. Breathable cotton or a linen blend keeps you comfortable all day, and a watch plus a crossbody finish it.
38. Longline Shirt With Slim Pants
One long vertical line is what a longline shirt builds, and the slim pants under it must be real trousers, not thin leggings, or the look turns sloppy. Leave it untucked and check that the side slits stop below the waistband. A long pendant helps the vertical effect, while a crossbody bag hanging low cuts straight across it. If the shirt looks shapeless, choose one with curved seams, a back pleat or a removable belt. Petite women should keep the hem at the upper thigh rather than near the knee. Taller women can go dramatic, especially with pants and shoes in the same dark color.
39. Asymmetrical Shirt With Midi Skirt
The one check I make with an asymmetrical shirt is where its longest point lands; if it ends at the widest part of your hip, it draws a line straight across it. Choose a draped, diagonal-hem or one-sided button shirt that still lets part of the waistband show, and pair it with a plain straight or A-line midi without heavy pleats. A monochrome palette makes the unusual shape look intentional. Pointed flats or minimalist heels, a structured bag and small geometric earrings echo the directional lines.
40. Draped Shirt With Satin Pants
Matte beside glossy is what makes this outfit work: a soft jersey, crepe or silk-blend draped shirt with wide-leg satin trousers keeps both from looking flat. Choose gathering at the shoulder or waist, and tuck the front lightly or pick a shirt that ends at the waistband. Satin trousers show every line, so smooth, no-show underwear matters here. For less shine, a washed or sanded satin is quieter. Pointed mules or slingbacks and a small structured bag finish it; skip most jewelry and let the drape do the work.
41. Western Shirt With Bootcut Jeans
Built-in structure is what I like about a Western shirt and bootcut jeans: the pointed yoke across the shoulders mirrors the flare at the hem. Look for denim, chambray or cotton with subtle yokes, snap buttons or chest pockets. The jeans should fit through the thigh and widen gently below the knee, in a dark wash with a high rise, and pointed ankle boots sit naturally under the flare. Add a leather belt and one bag, and stop there; too many themed accessories tip it into costume. Fuller busts do better with soft fabric and minimal pocket contrast, and a solid white Western shirt avoids an all-denim look.
42. Embroidered Shirt With Denim Skirt
Embroidery is best where the eye naturally goes, around the neckline, shoulders or cuffs, so I tuck the shirt fully when the stitching sits above the waist. Pair a cotton embroidered shirt with an A-line or straight midi denim skirt. Distressed denim and embroidery fight each other, so pick a clean finish. Take the bag color from the thread, or keep it tan or cream, and if the embroidery is colorful, keep jewelry small and neutral. Flat sandals or simple sneakers keep it easy from spring into early fall. Wash it inside out on a gentle cycle so the stitching doesn't snag.
43. Boho Shirt With Palazzo Pants
A flowing boho shirt with palazzo pants needs one firm point, or two loose, floaty pieces just blur together. I tuck the front or the whole shirt into a high-rise solid palazzo to create that waist. Platform sandals or low wedges hold up the wide hems, and a structured woven bag adds some contrast. Choose light fabrics that move without going transparent, and if the sleeves are very full, leave the neckline open and skip big necklaces. Petite women should choose narrower palazzos and a shorter shirt; curvier women tend to like a V neck and an adjustable tie.
44. Crochet Shirt With Tank And Shorts
Open by nature, crochet lets the tank underneath decide how the shirt reads. A close-fitting camisole in the same shade makes the stitches subtle, while a contrast color shows off the pattern. Wear an open-knit button-up over the cami with high-rise linen or cotton shorts. Crochet stretches when it's hung wet, so I always dry it flat. Large openings catch on rings and bracelets, so keep jewelry smooth. Leather slides or espadrilles and a woven tote make it an easy vacation outfit.
45. Sequin Shirt With Black Trousers
Small, matte or dark sequins in black, navy, pewter or deep green look grown-up, especially next to plain black trousers. Choose a relaxed button-up with a soft lining, since sequins scratch bare skin at the underarm. Tuck the front lightly into high-rise straight or wide-leg pants. The shirt reflects plenty of light already, so wear small earrings, carry a compact bag and leave the necklace at home. A blazer only works if it doesn't crush the embellishment, and sequins snag fine knits, so keep delicate cardigans away. Wear it to parties, concerts and evening dinners.
46. Velvet Shirt With Wide-Leg Pants
Being a pile fabric, velvet crushes where it's pressed and turns shiny if ironed directly, which is why I steam it from the inside. For tucking, a fluid velvet is far easier than a thick, rigid one. Pair a jewel-toned or neutral velvet shirt with tailored wide-leg pants that have a smooth waistband, open the collar slightly to make space around the face, and add pointed boots or low heels. Stick to one metal and avoid adding more glossy fabrics. If a full velvet shirt feels heavy, look for velvet panels or a shorter sleeve.
47. Faux Leather Shirt With Knit Skirt
Knit softens faux leather, and it's the contrast I'd pick for cold months. Choose a supple button-up in black, chocolate or burgundy rather than a stiff, heavily coated one, which creaks and doesn't breathe. A fitted column knit skirt suits a relaxed shirt; an A-line knit pairs with a tailored one. Tuck it partially or wear a waist-length version out. Because faux leather traps heat, a light camisole underneath makes it far more comfortable and lets you wear the shirt slightly open. Ankle boots and a structured bag finish it.
48. Corduroy Shirt With Straight-Leg Jeans
Wale means the number of ridges per inch, and for a shirt I always go fine-wale; it's thinner, drapes better and layers without the bulk of wide-wale cord. Rust, forest green, camel or cream all work with straight-leg jeans in a contrasting wash so the two don't blend together. Wear it buttoned and tucked, or open over a fitted tee like a light jacket. Large chest pockets add width, so keep the shoulder fit streamlined, and roll the sleeves to lighten the heavier fabric.
49. Shirt Jacket With T-Shirt And Jeans
A shacket is cut like a shirt in jacket-weight fabric, so it's the layer you take off at noon and put back on at five. Wear an olive, camel or plaid one open over a fitted white or black tee; the tee must sit close so the outer layer can stay loose without bulk. Straight-leg jeans and ankle boots or sneakers finish it, with the sleeves pushed up and a structured crossbody. Petite women should choose hip length rather than a knee-length oversized style, and curvier women may prefer curved side seams or a belt to use when it's buttoned.
50. Belted Shirt With Wide-Leg Jeans
For anyone who hates tucking, a belted shirt is the answer. Choose a long or tunic-length shirt with a removable self-tie belt, put the belt at your natural waist and pull a little fabric up so it blouses over. Check that the belt loops sit at the right height for your torso first; when they're too low, moving them is a simple alteration. Dark, mid or ecru wide-leg jeans, pointed flats or platforms and a structured bag do the rest. Fuller busts suit a narrower belt and an open neck, and petite women should choose a shorter shirt and cropped wide legs.
Four Tucks and When Each One Works
Nearly every outfit above says to tuck, but there are several ways to do it, and the right one depends on the shirt fabric and the rise of the bottoms.
- Full tuck: the whole hem goes into high-rise trousers or a skirt, then raise your arms once so a little fabric loosens over the waistband. It suits thin poplin, silk and satin; thick denim or flannel bunches up.
- Front tuck: tuck only the center front, about a hand's width either side of the placket, and let the sides and back hang. It shows the waistband without outlining the hips, and it's what I use most with jeans.
- Side tuck: tuck one side near the hipbone and leave the rest loose. The diagonal line works with straight jeans and a relaxed shirt.
- Military tuck: tuck fully, pinch the spare fabric at each side seam, fold it toward your back and tuck again. The shirt lies flat against the body, which helps under a pencil skirt or fitted trousers.
- Knot instead: on a long shirt you don't want to tuck, tie the two front tails at the waistband and keep the knot small.
A pale shirt tucked into pale trousers can show its hem as a ridge through the fabric. A shirt with a shorter, curved hem gets around that, and so does a bodysuit-style shirt that fastens underneath.
Collars, Cuffs and the Ironing Order
Woven shirts wrinkle, and most of the work of keeping them sharp comes down to how you wash them and the order you iron in.
- Iron while the shirt is still slightly damp: collar first (underside, then top), then cuffs, sleeves, the back and the front panels last.
- Use high heat for cotton and linen, low heat or a pressing cloth for silk, satin and synthetics. Velvet and corduroy go face down on a towel, or get steamed only.
- Button the shirt onto a wide, shaped hanger straight after ironing so the collar sets.
- Wash the underarms promptly. Deodorant and sweat build up and yellow pale shirts, and it lifts far more easily after one wear than after ten.
- Take out removable collar stays before washing; they can warp and leave marks.
I skip the dryer for linen and fitted cotton shirts. Heat shrinks cotton and sets creases, and a shirt hung damp on a hanger needs far less ironing.
A White, a Stripe and a Chambray First
A good shirt collection needs fit more than trends: shoulders that sit right, buttons that stay flat, hems that suit the way you tuck, and fabrics that suit your days. If you're starting from scratch, a white button-down, a blue stripe and a chambray shirt cover more than half the outfits above. Satin, velvet, lace and sequins can come later for evenings. Before buying any new shirt, I name three things already in the closet it would go with. If you can't think of three, leave it on the rail.
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