3 Wrinkle-Free Dress Shirts for $250 (orig. $345)

Aug 22, 2025, 1:16 PM•untuckit

The truth is you can’t go everywhere untucked. So, for when the occasion calls for it, we created this new dress shirt with the same fit you love, but extra length so you can tuck in when you need to. Designed by our fit experts, this elegant button-down is made from soft, 100% cotton fabric with our incredible Wrinkle-Free finish—perfect for a fall wedding or holiday party. It even has a dress-shirt collar that can support a tie. Just add one of our luxe sport coats and a pair of our flattering Classic Chino Pants to arrive looking like a million bucks. With all three classic shirts in your rotation, you’ll never have to worry about needing a sharp shirt in a flash.

Your big events call for the finest sport coat to instantly elevate any untucked look. Ours are made from lightweight wool woven at the famous Italian Reda mill for an extra-luxe look and feel. The material is breathable enough to keep you comfortable even when temperatures rise. Plus, the jacket is fully lined so it’s effortless to slip on and off. To look dressed up in a flash, wear one over a solid Wrinkle-Free shirt with a pair of our Classic Chinos for a sharp, classic style that works for any occasion.

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