This shirt is more affordable and slightly more square in shape than Ayr’s, with less drapey movement.

Sizes: 00–16 | Fabric: Cotton | Design details: Chest pocket, curved hem, relaxed fit | Price: $Įverlane was the brand we heard about the most, with several of our panelists explaining that for the price, the quality of its button-downs is top-tier. But if you’re looking for a looser fit, go with the size you usually take.

I sized down per her suggestion (I usually have to size up for button-downs) to get a more tailored classic cut. Unlike other button-downs that sometimes don’t close all the way, Sokolov uttered an immediate “Oh, this is great!” once she tried hers on. Kate Sokolov, co-founder of Social Goods, previously praised it for being big-bust-friendly. The shirt also features a boxy but not-too-big silhouette. “I feel put together but not trying too hard, polished but not preppy,” Pawling says. That keeps it from feeling too buttoned-up. It’s nicely opaque and not sheer at most you might see, say, a lacy black bra peeking through. Iva Pawling, founder of Richer Poorer, explains that its appearance of a classic starched shirt betrays how soft it really is. The Oxford cotton that the button-down is made of - which the company says is milled in Italy - has a pleasing weightiness without feeling too heavy. Ayr’s backstory for the shirt is that it “was a banker on Wall Street until she cashed out and started a new career as a florist on Nantucket.” I thought that was the right description once I tried it myself after requesting it from the brand - it has a look that falls somewhere between vintage Ralph Lauren and Ina Garten’s Hamptons uniform. The Deep End is the Platonic ideal of a button-down - the one I imagined in my head as I started reporting this guide. Sizes: XS–XL | Fabric: Cotton | Design details: Oversize pocket, longer back hem | Price: $$

Womens red button down shirt