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Valentine’s Day has its own special brand of emotions. If you’re single, every store, commercial and social media post will remind you of it — and if you’re coupled up, the pressure to do something amazing is at an all-time high. And while I can’t really change either scenario for you, I *can* give you advice on what to wear for Valentine’s Day, depending on what your plans look like.
Generally, the rule of thumb for any outfit is the same: You want to be comfortable, presentable and feel like yourself. Of course, all of those things exist on a sliding scale: Comfort can look like a pair of pajamas, but it can also mean your go-to knee-high boots that never hurt your feet. Presentable can mean a fancy cocktail dress and heels — but it can also mean a coordinating lounge set with a hair accessory. Most important of all, of course, is that you feel like you, even if you’re dressing for an occasion that’s yet to be revealed.
Ahead are five Valentine’s Day outfit ideas to try no matter your plans. And remember: It’s never about what you’re wearing, but rather, how you feel in it.
Wine Night With Friends
There’s no greater feeling than knowing you can be your true self with your friends. If you’re planning a chill night with those closest to you without the pressure of a commercialized holiday, wear whatever you’re most comfortable in: If you’re going out, maybe that’s jeans and a sweater. If you’re staying in, go for the absolute coziest outfit you can possibly find. For me, that’s a very oversized tee, flared sweats and cozy socks. Don’t judge.
Casa Magazines – The Papers Tee, $35
Bleusalt The Kaia Pant, $130
Brother Vellies Cloud Socks, $35
Staying In
Staying in with your partner is entirely different than a wine night in with your friends, but you still want to feel your best. Upgrade your loungewear to something that’ll make you feel sexy, too — I absolutely love SKIMS for this, but any two-piece matching set will do.
SKIMS Cozy Knit Scoop Neck Crop Top, $68
SKIMS Cozy Knit Pant, $88
Casual Night Out
If you’ve planned something chill with your partner for Valentine’s Day, here’s your chance to let your true style come out to play. I love the idea of wearing low-rise trousers with an open cardigan — or go truly cozy by pairing your favorite jeans with a hoodie and your favorite warm coat.
Oak + Fort Sherpa Coat, $168
The Frankie Shop Etienne Pants, $99
Nation LTD Mayumi Cardigan, $184
Fancy Night Out
A fancy night out doesn’t always call for a cocktail dress — but sometimes, it does. A cut-out dress in a midi length is a great option if you’d like to feel dressed up without freezing your tail off. Pair it with sparkly earrings and a pair of boots.
Mango Cut-Out Detail Dress, $99.99
AQUA Pavé Chandelier Earrings, $38
Gavin Boots, $87 (Orig. $92)
Wild Card
If your partner made plans and you have no idea what they are, make sure you double-check with them about any outfit restrictions you should keep in mind. (This is coming from someone who once rode a horse in 4-inch knee-high boots. Trust me, you want to be prepared.) Barring any major outfit restrictions, try to wear some version of the outfit you feel best in. For me, that’s wide-leg pants, a cropped sweater and some strappy heels.
& Other Stories Flared Press Crease Pants, $79
The Frankie Shop Niko Braided Sweater, $179
Strappy Heeled Leather Sandals, $89.90
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