What to Wear This Valentine’s Day, According to InsideHook Editors

Four InsideHook editors, four date night 'fits

February 10, 2023 10:23 am
a collage of Valentine's Day date night outfits on a pink background
Our editors are people, too. Here's what we're wearing this Valentine's Day.
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Here at InsideHook, we take both pride and pleasure in being your go-to source for all things culture, style, leisure and more — it’s demanding work, that involves reporting from the farthest flung reaches of the globe, liaising with the knowledgeable and famous, and occasionally, getting crunk while eating aged parm. But we, like you, are people, too. Smart, stylish, cool people, of course, but people nonetheless. People with deserving (see: demanding) partners and a rapidly approaching romantic holiday that demands not only presents, but some serious date night digs.

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As such, we’ve taken it upon ourselves to share what we’ll be wearing this Valentine’s Day, in hopes that it will inspire you to stylish heights…or, give you a cheat sheet to copy before you spoil the big night. From a rollneck look straight out of the JFK Jr. playbook to a relaxed ‘fit that anyone can pull off — so long as you have a couch, a flat-screen and a dream, that is — there’s a get-up for every occasion. Below, is what our editors are wearing this Valentine’s Day, and maybe, what you should be wearing too.

What InsideHook Editors Are Wearing This Valentine’s Day:

K.I.S.S. — Keep It Sweater, Stupid

If the occasion calls for a suit, by all means wear the suit. (I was initially going to recommend a no-fuss wool option I absolutely love in a pinch, but Everlane doesn’t make it anymore.) But if you’re like me and sartorially channeling When Harry Met Sally this February 14, go for a big sweater moment: specifically, the Fisherman’s Sweater from Quaker Marine, which is available in eight colors. Don’t size up, either, as you’ll want a trim fit to balance out J.Crew’s Giant-Fit Chinos, which I like in Catskill green. Pair these with some Blackstock & Weber Horse Bit Loafers (I’m in Minneapolis where we’re trudging around ice and snow, so a big lug sole is ideal) and you’ll be set. Oh, and just a heads up that your date will definitely want to steal this sweater. If the night goes well, go on and let them. Alex Lauer, Features Editor

High-Low Hi-Jinx

For this V-Day, I decided to throw together a fit centered around the classic blue blazer — I love to mix a little of the high and the low. Throw this on with a pair of light wash Levis 501’s and you will look like a celebrity from a 90’s movie premier. To top everything off I like to rock a more casual sweater or vest with a more thick textured t-shirt. Don’t be afraid to embrace the sweater vest. Can you potentially look like an English professor? Yes. But that doesn’t mean we shouldn’t take a few risks when it comes to date night. — Jordan Bowman, Senior Editor

Pushing Pleats

As my lovely partner is soon to find out, Valentine’s Day provides me with the perfect excuse to go egregiously hard in the ‘fit department for date night. In my playbook, this means only one thing: busting out the biggest, boldest pleats in my closet and putting them on full display. I’ll be opting for my beloved Drake’s Game Trousers, which are, alas, now sold out, but the British label’s recent ALD collaboration offers a similar high-waisted alternative (and comes with some build in street cred). An eye-catching crimson knit and accompanying checked overcoat should round out the ensemble quite nicely…the only issue now is avoiding any spaghetti and meatball spillage. — Paolo Sandoval, Assistant Editor

Enjoying a Night In

I’m going all out for the big night (in) — that means absolutely, 100% making sure the Uniqlo white tee and blue J. Crew cotton pajama bottoms I wear to bed most nights are clean. Or not. In other words, say you’ve been married 17 years without saying you’ve been married 17 years. Love ya, babe! — Greg Emmanuel, Editor-In-Chief

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