Before you buy a button-down, check three things: shoulder seams that land at your shoulder bone (or drop on purpose in an oversized cut), a fabric with a little weight so it does not gape at the bust, and a shirttail hem long enough to tuck. This li...
This is 100% cotton poplin with a slouchy, high-hip length, so it looks put together over leggings and also tucks into jeans without bunching. The stripes hide small wrinkles, which matters on days I am running around with my son and two dogs.
Madewell Poplin Oversized Button-Up Shirt in Stripe
Oxford cloth is heavier than poplin, so the buttons stay put and nothing gapes when you move. I like it half-tucked with trousers, and the organic cotton softens nicely after a few washes.
Everlane The Must-Have Oxford Shirt in White
When I want a button-down that feels dressier than cotton, silk charmeuse is the answer. It drapes instead of stiffening, and the flap pockets keep it from looking too precious. Hand wash and hang to dry, and it keeps looking good.
Madewell Silk Flap-Pocket Button-Up Shirt
The high-low hem is the detail that sold me, because the longer back covers you when you bend down to grab a dog leash. It comes in petite and plus sizing too, which is rare for a shirt this popular.
Anthropologie The Bennet Buttondown Shirt by Maeve
A linen and viscose blend gives you the airy look without the stiffness of pure linen, so it wrinkles less. I wear it open over a tank at the park and buttoned up with white jeans for dinner.
Madewell The Linen-Blend Oversized Shirt
If you want a button-down that borrows from athleisure, this 100% cotton poplin is it. The boxy, slightly cropped cut sits well on high-waisted joggers, and Nike suggests sizing down if you prefer it less spacious.
Nike Sportswear Chill Poplin Oversized Striped Top
Thomas Mason cotton feels crisp and polished, and the shirt is cut generously, so reviewers say not to size down. Mine gets worn open over a tee on weekends or tucked in when I need to look pulled together fast.
J.Crew Relaxed-fit Thomas Mason for J.Crew Shirt
A cami under a button-down solves the gaping-at-the-chest problem and lets you leave a few buttons open without worry. The recycled-nylon fabric is smooth, so it will not bunch under a silky shirt or a thin poplin one.
Madewell Seamless Crop Cami
This one is a silky cotton jersey, so it looks like a blouse but feels like a tee. It is semi-fitted, which keeps it tidy under a blazer without adding bulk at the waist. I would pick my usual size and roll the sleeves once.
The poplin has a bit of stretch and dries quickly, which is a big deal for a shirt you throw in a suitcase. It comes in regular, petite and tall lengths, so the sleeves and hem hit where they should.
Athleta Midday Relaxed Poplin Shirt
At 93% linen it breathes well in warm weather, and the soft stripe reads as classic rather than preppy. Linen creases by design, so I just give it a quick steam and move on with my day.
Madewell The Easy Shirt in Linen Blend
Densely woven cotton poplin gives you a crisp, cool feel without being see-through, which black and white shirts sometimes are. The half-placket makes it feel a little more modern than a standard button-down.
Everlane The Oversized Poplin Shirt in Black
Cinching an oversized shirt with a belt instantly gives you a waist. This leather belt is about 1.3 inches wide, worn at the hips, and the brass buckle works with jeans or trousers.
Madewell Medium Perfect Leather Belt
Fifty-five percent linen and forty-five percent cotton makes this one drapey but still structured. I like it for spring and fall because the long sleeves cover just enough when the temperature dips.
Anthropologie Maeve Kate Linen Cotton Classic Buttondown Shirt
Details like chambray piping and blue button thread make this feel more special than a basic oxford. Classic fit means it sits closer to the body than the oversized ones, which is good under a sweater.
J.Crew Classic-fit Oxford Cotton Shirt in Stripe
The darts are the thing here, because they give a body-skimming fit and keep the buttons from pulling across the bust. Satin takes a cool-water wash and a low iron, and it dresses up easily with trousers.
Madewell Darted Button-Up Shirt in Satin
The Dillon is cut without darts, so it has a straight, easy line that skims the body. Banana Republic publishes a fit guide, which helps when you are guessing at the size online. Good if you want a plain, dependable work shirt.
Banana Republic Dillon Classic-Fit Shirt
A tucked button-down looks best with a high rise and a wide leg, and this pair does both. Reviewers say it runs big, so I would size down, and the lyocell blend drapes without wrinkling too much.
Madewell The Harlow Wide-Leg Pant in Drapey Twill
A popover has fewer buttons, which means fewer chances of gaping. This one is 100% linen and has a boxy, airy shape that feels easy on a hot afternoon. Wash it cold and let it air dry for the softest texture.
Everlane Popover Shirt in Linen, Navy
The dolman sleeves make it comfortable to move in, with no tight armholes. Pair it with jeans and sneakers for school pickup, or with a black skirt for an evening out. It also folds small in a bag without creasing too badly.
Madewell Relaxed Dolman Button-Up Shirt in Satin
Chambray gives you a denim look at a lighter weight, so it works as a shirt on its own or a jacket-style layer over a tee. The chest flap pockets add a workwear feel, and I toss it on over leggings when the morning is cool and the afternoon is not.
Madewell Chambray Button-Up Workshirt
Stripes plus a silky finish gives you a blouse that feels dressier than your usual cotton shirts. I would wear it tucked into wide-leg trousers with flats, and it is easy to layer under a cardigan.
Anthropologie Maeve Silky Striped Buttondown
Flannel is the cozy cousin of the classic button-down, and this one is slightly oversized with a 28-inch body length that covers a bit past the hip. Wear it buttoned with jeans or open over a cami once the weather turns chilly.