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: $$
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