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Bralette and High-Waist Briefs For a laid-back yet fashionable look, a bralette paired with high-waist briefs is a good combo

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TWP makes this button-up in a variety of fabric options, including linen and cotton poplin, and they come and go seasonally

If You're Spending Under $500 Total Suit: Spier & Mackay fresco wool in stone or dusty blue ($400) Shirt: Charles Tyrwhitt non-iron in white ($60 when on sale) Tie: A knit tie from The Tie Bar ($25) Shoes: You already own brown derbies