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SD 003 Boxer, $48, by Special Delivery, available at SpecialDeliveryNYC.com
Nerdy prints on undies may be cute, but as you grow older, it's what's inside your trunks that should be making a bold statement. These minimalist, made-in-USA boxer shorts boast a perfect balance between relaxed fit and tailored support thanks to a soft woven cotton fabrication, and they're available in six colors. Upgrade those drawers at once!