2 Replies to “What Should I Wear on a Nice First Date?”

  1. Depends on your setting and the image you want to present, but my default has always been a pair of dark, fitted jeans, a collared dress shirt with a bit of pattern and color to it, and a soft-shouldered casual sports jacket, with leather dress shoes and a matching belt. I usually throw a decorative belt buckle and a colored pocket square into the mix to keep it looking casual.

    Things to stay away from: a full suit (makes you look way too formal), neckties (if it’s an evening date it’s too late for neckties anyway), T-shirts with logos or graphics on them, work jeans, athletic shoes, anything saggy. Keep it simple, well-fitted, and smart-looking but not formal.

  2. A video reply to a similar question – I was actually on the road when I made this one, so my outfit and setting may seem a little unusual to regular watchers!

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