Kate Sokolov, co-founder of Social Goods, raved about it when I set out in search of big-bust-friendly button-downs. It isn’t the first time I heard about the glories of the Deep End, either. It’s so dependable that Pawling wears it with everything from more formal pants to cutoffs, with rolled-up sleeves. “I feel put together but not trying too hard, polished but not preppy,” she says. Like the oversize men’s shirts Pawling relied on until she found this one, Ayr’s works so well because it has the “look of a starched oxford shirt” that betrays how soft it really is, making for a boxy but not-too-big silhouette. It’s exactly what Iva Pawling, founder of Richer Poorer, had in mind when her button-down-mania began. Ultimately, Ayr’s Deep End shirt won because it’s the Platonic ideal of a button-down: You can imagine wearing it anywhere in any which way. What made crowning the best of the very best challenging was that there wasn’t one that took the most-mentioned title easily. Sizes XS–XL | Cotton | Oversize pocket, longer back hem, buttons on sleeves | $$ The ones that made it onto this list are categorized as either under $100 ($), under $200 ($$), and over $200 ($$$). But our focus was on finding shirts that were worth it, and whenever one was pricier, we tried to include a more affordable alternative. Price: The cost-per-wear philosophy is helpful here - it makes sense to invest in a button-down since it’s pretty much dress code–proof. A note: Our panel favored oversize styles overall (think Carrie Bradshaw’s post-pond look versus Carolina Herrera’s runway-ready tops), but we’ve noted when a button-down is more tailored.

All of these details are included below for easy reference. Other than that, anything’s really fair game, whether that’s pockets, ruffle pleats, curved hems, or puffed sleeves. In fact, button-down and button-up are used interchangeably to refer to any shirt with a row of buttons and a collar. It’s cheaper (compared to something like silk) and wears well, especially on the wrinkle-fighting front (unlike linen).ĭesign: The rule that a button-down must have buttons on each end of the collar (hence the name) isn’t enforced as much in modern womenswear. Sizes: As always with any kind of apparel, we’re focused on featuring button-downs offered in a wider selection of sizes rather than the frustratingly limited (but all-too-common) small-to-large range.įabric: Traditionally, cotton is the material of choice for button-downs - see the classic oxford shirt - so that’s what most of the ones on this list are made of.

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