8 Valentine’s Day Outfit Inspiration for Every Event

Call me a romantic, but I’m a sucker for Valentine’s Day. Fragrant roses, decadent chocolates, and handwritten notes make my heart sing. What I don’t love about the romantic holiday is dressing for it—especially since I live in New York City, and it’s always freezing on February 14th.

For me, assembling a Valentine’s Day outfit isn’t as simple as slipping into a dress. There’s lots of layering and accessorizing involved. To avoid agonizing over my V-Day wardrobe this year, I’ve curated an edit of cozy-chic looks that will rise to any occasion.

If I decide to get together with my girls for a Galentine’s brunch, I’ll wear a sweater, a mini skirt, sheer tights, and pumps. If my boyfriend surprises me with a candlelit dinner, I’ll choose a lace-trimmed dress, a blazer, and slingbacks. And in the event that sub-zero temperatures cause us to hibernate indoors, I’ll bundle up in polished pajamas and fuzzy slippers.

Scroll on if you’d like to steal a page from my style playbook. You’re guaranteed to fall head over heels for these Cupid-approved outfits.

For a Fancy Dinner

Upscale meals call for polished satin dresses. I’d suggest a lace-trimmed option, as this dainty style just so happens to be trending this season. Layer up with a blazer and a floor-grazing coat, and embellish with slingbacks and slouchy shoulder bag.

Aritzia

Lamplight Satin Dress

Open Edit

The Icon Relaxed Blazer

Mango

Mona Slingback Pump

For a Galentine’s Get-Together

While Valentine’s Day invites shades of red and pink, there’s a way to embrace the color palette without looking too costume-y. Opt for a burgundy sweater paired with a thigh-grazing skirt, then play peekaboo with cherry-colored sheer tights and strappy sandals. Of course, make sure to keep warm in a hefty wool jacket.

Reformation

Florie Twist Front Sweater

Wolford

Velvet De Luxe 66 Tights

COS

Boiled Merino Wool Mini Skirt

Tony Bianco

Mariah Sandal

For a Cocktail Date

Chocolate brown is fashion’s favorite color, and it’s not going away anytime soon. Sample the sweet shade with a sumptuous faux fur coat and a form-fitting dress. Knee-high boots and gold jewelry will ground the look nicely.

Eloquii

Funnel Neck Faux Leather Midi Dress

Madewell

The Emilie Tall Boot

petit moments

Ashley Earrings

For a Game Night

If you’re going to the arcade or the bowling alley, you’ll likely be on your feet all night. So, pick a look that prioritizes comfort. Cushioned sneakers, a plush sweater, and a stretchy pair of jeans will do just that. Give your ensemble a cool-girl edge with an ‘80s-inspired leather jacket.

Abercrombie & Fitch

Relaxed Mockneck Vegan Leather Bomber Jacket

Gap

Low Rise ’90s Loose Jeans

L’Academie

By Marianna Ronny Turtleneck Sweater

Adidas

Handball Spezial Shoes

For a Casual Daytime Date

Keep things laid-back with a relaxed pullover and a pair of wide-leg denim bottoms. Styled with a sweeping coat and a hardware-adorned handbag, it’s the type of look that’ll take you from eating lunch to roaming around a museum.

Everlane

The Cotton Honeycomb Square Crew

DL1961

Karmine High Rise Refined Wide Leg Jeans

DeMellier

Vancouver Suede Shoulder Bag

For a Picnic or a Sunset Walk

If you live somewhere warm and plan on spending Valentine’s Day outdoors, I envy you, and will be living vicariously through you by picking out your outfit. Stick to a streamlined style agenda with a tee-and-jeans uniform, but shake things up a bit with a colorful cardigan and leopard-print flats.

Line & Dot

Ayla Double Layered Sweater

Levi

Ribcage Straight Ankle Women’s Jeans (Plus Size)

For a Night In

After a Valentine’s Day spent out and about, I can’t wait to return home and slip into a set of snug pajamas. I’ll wear them with a jumper and a pair of fuzzy slippers. As for accessories? A glass of wine in hand will do.