What Men Should Really Wear on Dates

Even if it's your first or your umpteenth date, for coffee or for steak, you should always still dress to impress.
ILLUSTRATOR Jasrelle Serrano

If there’s an occasion that warrants looking good, it’s a date—whether it’s the first or the umpteenth. Of course, you’d always want to show best-dressed version of yourself.  You’d also want to be comfortable and also make your date feel comfortable around you. You wouldn’t want to overdo things (or outdo her) with sartorial pyrotechnics but you wouldn’t want to look boring either. “Dressing well is a way to make a woman feel that you take her seriously. It also lends confidence, and is an indicator of good social skills because it shows that you care enough to want to make a positive impression,” says PR maven and stylish restaurateur (Your Local, Hey Handsome) Celine Lim. And well, if we’re talking about the first date, you don’t get a second chance to make a first impression, right? Putting thought into your wardrobe also tells her that you always want to look your best for her, which is kind of an unspoken compliment. So what should you wear? First, determine what kind of date it’ll be.


The Talk-of-the-Town Restaurant Date You can win style points by wearing a shirt with small patterns like gingham or stripes and slim (not skinny) pants or dark jeans. Stay away from skinnys as you’d definitely want mobility and comfort throughout the evening. You can also throw on a sweater on top of the shirt for a bit of a preppy look if that is more your style. Oxfords will help strike the right balance between dressy and laid-back. “When in doubt, head-to-toe A.P.C. never offends anyone,” advises Martine Cajucom, stylephile and co-owner of Sunnies and Sunnies Cafe.

Sweater by Diesel; shirt by T.M. Lewin; jeans by Levi’s; shoes by Louis Vuitton.


Cocktails by the Beach Date This kind of date allows you to dress comfortably, but you’d still want to look effortlessly sophisticated and not ready for a swim. Blogger and businesswoman Cat Arambulo Antonio suggests “a white linen long-sleeve collared top, white linen pants, and flip-flops.” Yes, it’s not every day that you can pull off an all-white outfit, but this is one of those moments, and you will look dashing.

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Shirt by Thomas Pink; pants by H&M; shoes by Bally.


The Five-Star Dinner Date Do you wear a full suit? A sport coat will do the trick. It’s best to break away from the boardroom look of course and go with light-colored coats like a gray or camel or beige. “Personally, my preferred look is a mix of classic and relaxed sophistication, which means a well-pressed shirt, impeccably fitting pants, a good watch, a stylish pair of shoes, and a light jacket. You can also throw in a pocket square if that’s more in line with your personality,” Celine quips. “Not too much jewelry either.” It’s best to stick with a two-color palette for this outfit, including the shoes. Loafers will complete this look.

Sport coat by Acne Studios; shirt by Giorgio Armani; pants by Bottega Veneta; shoes by Bally; watch by Patek Philippe.



The First (Coffee) Date “Perfectly lived-in jeans and crew neck basics are my favorite casual pieces for men,” says Martine. It’s simple yet still dapper. And fashion no-nos? “Rubber shoes!” according to Cat. Though the date is over coffee, don’t go overboard on the “casual” or look like you just came from a run. Wearing suede sneakers is the smarter choice. Also, stay away from “fedoras and too much cologne,” adds Martine.

Polo shirt by Givenchy; jeans by Diesel; shoes by Tod’s.

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