If I could keep only one shirt in a client's closet, it would be a striped button-down. It sits between polished and relaxed better than almost anything, so a crisp blue-and-white poplin goes to the office and an oversized linen version runs weekend errands. The hard part is knowing where to start, because the shirt works with nearly everything. Below are 30 full outfits that show how I'd wear one through the year: tucked, half-tucked, knotted, layered and worn open, each built from pieces most closets already hold.
Stripe Width, Fabric and Fit Before You Buy
Not every striped shirt does every job on this list. Before a client buys one, I look at three things: how wide the stripe is, what the fabric is and how the shirt fits through the shoulder and bust.
Stripe width
Fine pinstripes read almost solid from a distance and suit offices and dressier outfits. Medium stripes are the most versatile. Bold, wide stripes are casual and graphic, and on a smaller frame they can overpower, so keep them for weekend shirts. Fine stripes can shimmer on camera, which matters if you'll be photographed.
Fabric
- Poplin is crisp and smooth, best for tucking into trousers and skirts.
- Oxford cloth is thicker and softer, good for casual and layered looks.
- Linen is cool and creases easily, ideal for summer and beach outfits.
- Washed or brushed cotton drapes loosely and suits oversized styling.
Fit
Check the button placket at the bust while seated; if it gaps, size up and have the waist taken in. For a fitted shirt, the shoulder seam should sit at your shoulder bone. For an oversized one, it can drop a little, but the sleeve should still let your hand show when your arm hangs.
1. Striped button down with blue jeans outfit
A blue-and-white stripe with straight-leg blue jeans is the version I'd build first. Leave the top two buttons open, roll the cuffs once or twice and half-tuck the front into medium-wash denim. The stripes and solid blue sit together without fighting because they share a color. White leather sneakers keep it casual, and a brown leather belt warms the cool palette. Add a canvas tote and tortoiseshell sunglasses, and you have the outfit you'll come back to every week.
2. Striped button down with white jeans outfit
White jeans make a striped shirt look crisper and more preppy. Tuck a navy-and-white vertical stripe fully into high-waisted white straight-leg jeans for a clean, slightly nautical outfit. Thin white denim can show pocket bags through the front, so I always check a pair in daylight before buying. Tan leather for the belt, flats or sandals and a structured crossbody warms the palette. A light cardigan over the shoulders adds a borrowed-from-the-Hamptons touch.
3. Striped button down with wide leg trousers outfit
Wide-leg trousers give a striped shirt a long, tailored line. Tuck a fitted or slightly oversized stripe into high-waisted trousers in cream, camel or black that just graze the floor. The volume below balances the collar and placket above. I hem wide trousers with the shoes the client will wear most, because an inch too long and the hem frays on pavement within weeks. Pointed mules or low block heels, a leather tote and gold jewelry finish it; a tonal blazer on top adds authority.
4. Striped button down with black trousers outfit
Black trousers ground a striped shirt and make it look sharp straight away. Tuck a black-and-white or navy-and-white stripe into cigarette-leg or slim-straight black trousers for client meetings, dinner or a gallery opening. Navy stripes with black trousers can look slightly off in daylight, so I prefer black-and-white stripes here for a clean match. Pointed heels or sleek loafers keep the lower half unbroken, and a black belt links the two halves. Silver jewelry and a black clutch finish it.
5. Striped button down with denim shorts outfit
Hot days call for denim shorts. Wear an oversized stripe open over a white ribbed tank with mid-length cutoffs, sleeves rolled loose and the tank showing. A shirt that's too long can cover the shorts entirely, so I'd keep the shirt hem no more than a few inches below the shorts. Flat leather sandals or espadrilles, a woven market tote and layered gold necklaces make it feel like vacation. For a neater line, button it halfway and front-tuck it.
6. Striped button down with white shorts outfit
Tailored white shorts with a striped shirt is warm-weather polish at its simplest. A pastel or classic blue stripe tucked into white shorts looks fresh and stays cool. I'd choose shorts with a lining or in thicker cotton twill, since thin white fabric turns see-through in bright sun. Leave a few top buttons open for an unstudied feel. Raffia flats or tan sandals, a woven headband and a rattan bag suit farmers' markets and baby showers.
7. Striped button down with mini skirt outfit
A striped shirt with a mini skirt feels young and playful. Half-tuck an oversized blue-and-white stripe into a black or denim A-line mini for daytime, or match it with a stripe mini and drape a denim jacket over the shoulders. The shirt's tails add bulk under a short skirt, so I tie them or trim the tuck to the front only. White sneakers or chunky loafers keep it casual. For evening, switch to a leather mini, sheer black tights and lace-up heeled boots.
8. Striped button down with midi skirt outfit
A striped shirt tucked into a flowing midi skirt is one of my favorite dressier pairings. A bias-cut satin or A-line cotton midi in olive, champagne or blush lets the stripe stand out while keeping the shape soft. Front-tuck the shirt and roll the sleeves; a full tuck under a bias skirt often bunches at the back waist. Barely-there heeled sandals and a slim leather bag keep it light for an outdoor wedding, a bridal shower or a date night when you'd rather not wear a dress.
9. Striped button down with pencil skirt outfit
For workdays that need polish, tuck a fine-stripe blue-and-white poplin into a fitted navy, black or charcoal pencil skirt that ends just below the knee. Pencil skirts show every bump of a shirt's tails, so I choose a slimmer cut shirt or tuck the tails into the waistband of a slip. A slim belt sharpens the waist, and neutral pointed pumps lengthen the leg. A watch, studs and a structured leather satchel are all the extras it needs. The stripe breaks up the solid skirt without competing with it.
10. Striped button down with pleated skirt outfit
A pleated midi or maxi adds movement to a striped shirt's crisp lines. Tuck a fitted white-and-navy stripe into a metallic, plaid or solid pleated skirt. Mixing stripes with plaid works when one pattern is much smaller than the other, so I'd pair a fine shirt stripe with a larger check. Accordion pleats catch light as you walk. Square-toe mules or ballet flats and a chain-strap bag carry it from desk to dinner; switch to a smaller bag and add bold lipstick for evening.
11. Striped button down with satin skirt outfit
Matte cotton against liquid satin is the texture mix that makes an outfit look expensive. Tuck a green-and-white or pink-and-white stripe into a bias-cut olive or champagne satin midi. Cotton shirts can create static that sticks satin to your legs, so a light spray of anti-static or a slip underneath helps. Slim heeled sandals or strappy mules keep it sleek, and a tonal clutch with fine gold jewelry lets the skirt lead for cocktail parties and evening events.
12. Striped button down with leather pants outfit
Leather pants give a striped shirt a rock edge. Tuck a blue-and-white or black-and-white stripe into high-waisted slim or straight black leather pants, roll the sleeves and open a few buttons at the neck. Leather pants stretch with wear, so I'd buy them snug at the waist and hip rather than comfortable. Heeled ankle boots or pointed stilettos extend the leg, and a black clutch with silver ties it together. A wool coat or leather jacket over the top suits cool-weather dinners.
13. Striped button down with cargo pants outfit
Relaxed cargo pants in khaki, olive or black with a tucked oversized stripe make a practical street-style outfit. The shirt's crisp collar keeps the utility pants from looking sloppy. Tucking a big shirt into cargos adds bulk at the hip, so I tuck only the front and let the back fall loose. Chunky sneakers or lug-sole boots, a canvas or nylon crossbody, a cap and chunky silver hoops suit travel days and weekend coffee walks.
14. Striped button down with linen pants outfit
A striped shirt with linen trousers comes back every summer because it works. Choose a linen-blend shirt in soft blue or sage stripe and tuck it into relaxed wide-leg linen pants in white or beige. Linen wrinkles fast, and I tell clients to accept it; the creases are part of the look, though a blend creases less if that bothers you. Flat leather sandals, a woven tote, oversized sunglasses, a gold chain and stacked rings suit beachside lunches and travel days.
15. Striped button down with corduroy pants outfit
Corduroy pants bring fall texture to a striped shirt. Tuck a cream-and-tan or rust-and-ivory stripe into camel, chocolate or olive corduroy straight-leg pants, then add a suede belt, leather ankle boots and a wool blazer or cardigan. Wide-wale cord adds visible bulk at the hip, so if that's a concern, pick a fine or medium wale. The matte cord and crisp cotton contrast without clashing. A leather satchel and tortoise clips suit Thanksgiving or a fall brunch.
16. Striped button down with joggers outfit
A striped button-down with joggers looks intentional only if the joggers look tailored. Choose cotton twill, crepe or a structured knit with a flat front, and tuck the shirt in cleanly. Fleece joggers with a cuffed ankle drag the whole outfit back to the gym. A tonal palette, white-on-cream or navy-on-navy, keeps it modern. White sneakers, a belt bag, minimal gold and a neat bun suit airport days, school pickups and working from home.
17. Striped button down with culottes outfit
Culottes have a swingy, cropped shape that suits a crisp striped shirt. Tuck a fitted stripe poplin into high-waisted black or navy culottes, and let the cropped hem show strappy heeled sandals or pointed flats. Because culottes cut the leg at mid-calf, I'd always add a little heel or a pointed toe on a petite frame to keep the leg from looking short. A top-handle bag and bold sunglasses suit a creative office, a gallery opening or a baby shower.
18. Striped button down with bell bottom jeans outfit
Pairing a striped shirt with high-waisted bell-bottom jeans gives it 70s energy. The flare balances an oversized shirt and makes a long frame. Flares need the hem set with the shoe you'll wear, ideally platform clogs or heeled boots, so the denim just touches the floor. Tuck the shirt in fully or knot it at the waist. A deep side part, statement sunglasses and a suede shoulder bag add the vintage mood without tipping into costume.
19. Striped button down with boyfriend jeans outfit
Boyfriend jeans make a striped shirt feel slouchier and cooler. Choose an oversized shirt in a soft, washed stripe and wear it untucked and open over relaxed, raw-hem jeans, with a simple tank underneath. Two loose pieces can overwhelm a smaller frame, so I'd roll the jeans to show the ankle and push the shirt sleeves up to the forearm. White sneakers or flat slides, a cap, a canvas tote and minimal jewelry suit a lazy Sunday or a long flight.
20. Striped button down with overalls outfit
A fitted long-sleeve stripe under classic denim bib overalls is practical and fun. Roll the cuffs of both shirt and overalls for a clean, cropped line. A slim-fitting shirt matters here, since a full shirt bunches under the bib and the side openings. White canvas sneakers or leather ankle boots suit apple picking and fall markets. Swap to black or olive overalls with a wool beanie for a city version; the stripe at the bib keeps all that denim from looking heavy.
21. Striped button down under a blazer outfit
A blazer over a striped shirt is smart-casual done right. Layer a khaki, navy or camel single-breasted blazer over a crisp blue-and-white stripe, tucked into matching trousers or dark denim. I wear the blazer open and set the shirt collar over the lapels only when the collar is soft; a stiff collar looks neater tucked inside. Loafers or low block heels and a structured tote make it office-ready, and sneakers with a crossbody take it casual.
22. Striped button down with sweater vest outfit
A cream or oatmeal sweater vest over a blue-and-white stripe, with the collar and cuffs showing, is the easiest way into the academic look. Wide-leg trousers and loafers keep it polished; jeans and chunky boots relax it. The shirt underneath should be slim through the body, because extra fabric bunches under a fitted vest and creates lumps at the waist. The knit over crisp cotton adds depth, and wire-rim glasses finish the dark-academia mood.
23. Striped button down layered over a turtleneck outfit
A thin turtleneck under an open striped shirt adds warmth and a graphic frame. Choose a black, cream or camel fine-gauge turtleneck, layer the unbuttoned stripe on top and tuck both into high-waisted trousers or a denim midi. Only a fine knit works under a shirt; a chunky turtleneck makes the shirt strain at the shoulders. The shirt acts like a light jacket here. Ankle boots and a wool coat finish it for museum visits and winter weekends.
24. Striped button down open over a tank top outfit
An oversized striped shirt worn open over a ribbed tank is the easiest layering trick I know. Tuck a white or black tank into relaxed jeans or linen shorts and let the shirt float. It doubles as sun cover for your shoulders on a long day outdoors. Flat sandals, layered necklaces and a woven bag suit beachside cafes and road trips. For something breezier, swap the tank for a bandeau.
25. Striped button down tied at the waist outfit
Tying a striped shirt at the waist turns it into a cropped top for high-waisted bottoms. Knot a light cotton stripe just above the navel and wear it with high-rise wide-leg trousers or a maxi skirt. Thick poplin makes a bulky knot, so I'd use a softer cotton or linen shirt for this. The knot marks the waist without a belt, and the vertical stripes still lengthen the torso. Flat sandals or espadrilles and big sunglasses give it a 50s vacation feel.
26. Striped button down half tuck outfit
The half-tuck is a small move that changes the whole outfit. Tuck one side of a striped shirt into jeans, trousers or a skirt and let the other side hang loose; it breaks up the block of fabric and creates an angled line. A blue-and-white stripe half-tucked into dark straight-leg jeans with slingbacks and a leather shoulder bag is the classic version. It works best on shirts with a curved hem, because a straight hem bunches on the loose side.
27. Striped button down beach cover up outfit
An oversized cotton or linen striped shirt is a ready-made beach cover-up. Worn open over a bikini or one-piece, it covers your shoulders and the tops of your thighs and still lets air through. Linen dries faster than heavy cotton if it gets splashed. Roll the sleeves high and leave it open, or button one or two in the middle. A wide-brim straw hat, flat slides and a roomy tote take you from the pool to lunch.
28. Striped button down with denim jacket outfit
A striped shirt breaks up all-blue double denim. Layer a blue-and-white stripe under a slightly oversized denim jacket with white or ecru jeans for a crisp mix of three textures. I'd keep the jacket a different wash from the shirt's blue, so the two blues don't almost-match. White sneakers or low-profile leather trainers, a canvas belt and minimal gold suit spring and fall weekends. For a dressier take, swap the jeans for a denim midi and heeled sandals.
29. Striped button down with leather skirt outfit
A leather skirt gives a striped shirt edge and texture. Tuck a fitted black-and-white stripe into a black leather A-line or pencil mini with opaque tights and heeled ankle boots for a sleek cold-weather outfit. Leather skirts crease across the lap from sitting, and a warm cloth smooths most of those lines out. The stripe keeps the dark lower half from feeling heavy. Silver jewelry and a black leather shoulder bag carry it from the office to evening drinks.
30. Striped button down layered over a dress outfit
An oversized striped shirt makes a good light topper over a slip or midi dress. Leave it open over a neutral satin slip for evening, or button it halfway over a fitted ribbed knit dress for daytime. Belting the shirt at the waist over the dress defines your shape and turns the shirt into a jacket. The shirt should be longer than your hip but shorter than the dress hem, or the layers look accidental. Strappy sandals or pointed mules and a shoulder bag keep it light into fall.
Keeping Collars Crisp and Whites Bright
A striped shirt looks sharp only while its collar and white stripes stay clean. These are the habits I recommend so one good shirt lasts for years.
- Pre-treat the inside of the collar and cuffs before every wash; that's where skin oil yellows the white stripes first.
- Wash on a gentle cycle in cool or warm water, never hot, so colored stripes don't bleed into the white.
- Hang the shirt on a hanger while damp and smooth the collar and placket by hand; it cuts ironing time in half.
- Iron the collar from the points inward to avoid creases at the tips, then do the cuffs, sleeves and body.
- Remove collar stays before washing if your shirt has them, and use them again once it is pressed.
Linen and washed cotton shirts can skip the iron for casual looks; a few minutes of steam over a hot shower relaxes the worst wrinkles. Keep poplin pressed, since that crispness is what makes it look polished.
Treating the Stripe as a Neutral
Treat a striped button-down as a neutral, and it goes with denim, leather, linen, corduroy and satin alike. Try a different tuck each week, layer it under knits when it's cold and over swimsuits when it's hot, and pay attention to the stripe width and fabric weight that suit you. One good shirt, styled these ways, covers more of the year than almost anything else in your closet.
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