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