Ask Harry: What Do I Wear on a Date?
Our guide for guys on getting dressed to impress on a romantic rendezvous.
No matter if you have no trouble whatsoever with getting dressed on the daily, when it comes to choosing a date night outfit, almost all sartorial common sense can promptly fly out the window.
Even for the most experienced ‘fit curators, the unavoidable excitement (hysteria?) induced by dating can be enough to put one off his game.
If you’ve got a special evening penciled into the books and want to ensure you get your get-up right, simply look to these three date night ideas.
Classy-Yet-Casual
Going out with someone special during the day? Keep it casual—think coffee, a park stroll, or small plates at your go-to spot. A great pair of denim (bonus if it’s white), a comfy cashmere sweater or crisp tee, and a soft wool overshirt or chore jacket will do the trick. Remember: the softer the material, the longer your date will want to hold onto you.
Make a Statement
Heading to a hot new spot? Whether it’s a first date or a landmark night, elevate your look by going smart-casual. Try chinos or jeans with a patterned blazer or cashmere overshirt for a tailored feel that’s not too formal. Add loafers or sophisticated sneakers for versatility — you’ll look sharp without trying too hard.
Dressed to the Nines
For upscale dinners, theatre performances, or gallery dates, skip the overpriced bubbly — what really matters is looking (and feeling) your sharpest. Flex your tailoring skills with a soft-shouldered suit, though keep it cool with sleek knitwear instead of a shirt and tie. This look's all about masculine style with just the right amount of mystery.
