What to Wear on Valentine’s Day, Depending on Your Date

Playing It Cool Versus Going All Out

By UrbanDaddy Staff ·
Congratulations, you’ve got a date for Valentine’s Day.

First: make sure to read up on this handy guide to all things Cupid-friendly we’ve put together here.

Second: make sure you’ve got something to wear.

Naturally, we can help you with that, too. But that all depends on what kind of date you’re going on.

Let’s say it’s a casual early-in-the-relationship—possibly app-based—dinner somewhere low-key. Or maybe you planned this dinner out a month in advance and called the maître d’ to nail down the perfect fireside table for two, and things are getting serious. Those are two different scenarios that require two different ensembles. So we tapped our two style guys in the know to lay out a sartorial game plan for each date night.

The Fancy Entering-the-Serious-Stage Date Night
“Obviously, you’re going all out with the fancy dinner reservations and planning the night to a T. So there’s no reason to stop short with your getup. Dress to impress, with the following five items...” —Najib Benouar

Suitsupply Havana Grey Check Suit

Charvet Flower Lapel Pin

Drake’s of London White Cotton Dress Shirt

Paul Smith Heart Print Dot Tie

Gucci Horsebit Loafers

The New Relationship Stage
“So you just found someone you like, and as luck would have it, you found them right before Valentine’s Day. It seems a little overboard to go on some sort of three-hour tasting-menu journey so early in a relationship, so the entire affair calls for not only a more casual setting, but a more casual wardrobe. You can’t be a slob, obviously, but you’re looking for that elusive ‘cool’ quotient. Here’s how to work that.” —Geoff Rynex

Ami Zipped Shearling Jacket

Officine Générale Ethan Japanese Flannel Shirt

Deveaux Elasticated Pintuck Pant

Grenson Archie Brogues

Larsson & Jennings Lucano Watch

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