Products you buy through our links may earn us a commission. Oh, and if something's out of stock, oops, it was there (and all prices were accurate) at time of publication.
I’m a staunch believer that any plan is a good plan when it comes to Valentine’s Day. So whether you’re heading to the couch or going out to dinner with 10 of your best friends, both are perfect ways to celebrate. Either way, you’re going to need an outfit, and I’ve found everything from dresses dripping in hearts to more subtle loungewear you’ll live in all year. You know you love me.
Need gift ideas? Check out our Valentine’s Day gift guides here.
Drinks Date

A bodycon dress to grab in a few colors…
You really can’t go wrong with a bodycon number. This one has long sleeves to keep you warm, a flattering square neckline, and a back slit to leave them stunned when you walk away. It has enough stretch to be comfortable, and comes in pink as well as several neutral colors. ($22, Target)

A bodysuit you can layer…
One thing I vividly remember about watching Pretty Little Liars in college is how no matter the situation — putting on their sleuthing caps or getting locked in a dressing room with a snake (tell me you remember this) — the girls would always be wearing a lacy bodysuit under their fabulous outfits. This bodysuit is giving 2010s teen drama, with its lacy V-neck and open back. Throw a sweater on over it and you’re ready for anything. ($39.95, Free People)

A cashmere sweater for understated elegance…
In my opinion, the perfect drinks date outfit is a sweater that fits you perfectly, your favorite pair of jeans, and heels. This cashmere crew is a total classic, and it comes in red and a deep burgundy that work well for the occasion. You’ll feel put-together but not like you’re trying too hard, especially if you’re going on a first date (I applaud you). ($50, Quince)

A shirtdress you’ll also wear to the office…
To dress it up a bit, go classic with this shirtdress. It’s made of cotton poplin that looks polished, but it has some stretch, so you’ll be comfy. The wide collar looks good with a slicked-back hairstyle, and the included belt is a nice touch. Wear it with a blazer to work once you’re done celebrating. ($188, Universal Standard)
Fancy Dinner

A mini dress that’s cute enough to eat…
This year for Valentine’s Day, I’m leaning into the literal. I’m talking hearts everywhere, pink and red, you name it. This dress fits the bill, with its adorable silhouette adorned with sequin hearts. I love the idea of wearing this with tights and a big, fuzzy fur coat you can take off once you’re at the table. ($158, Anthropologie)

A heart pendant to pass down…
If you’re going to treat yourself to something, why not a piece of jewelry that’ll be the next family heirloom? One side of this heart necklace is the stone of your choice — from mother of pearl to turquoise — and the other side is etched 14-karat gold. It’s two necklaces in one, and no matter how you wear it, you’ll never want to take it off. ($899, Effy)

A heart mini dress to help you show off…
This is one of the cutest dresses I’ve ever seen. It has puff sleeves for drama, rhinestone hearts up the front that say you’re in love (with yourself in this dress), and a cutout for a hint of skin. When you show up in this, you’re the main course. ($83.97, Eloquii)

A slingback heel you’ll wear all the time…
If you’re considering a new pair of shoes for the holiday, make it these on-trend heels. The pointed-toe slingback looks sophisticated peeping out of trousers or with tights and a dress. They come in three textured colors. ($298, Reformation)
Girls Night Out

An embroidered mini skirt you’ll wear on vacation later…
Girls night out is the perfect time to go literal with your outfit. This skirt features embroidery that reminds me of homemade, cut-out Valentine’s Day cards, and the eyelet trim is so pretty. Grab the matching top for a full-on girly ’fit your friends will love. More to love: For the month of January, the brand is donating 10% of all order proceeds to help Los Angeles rebuild after the wildfires. ($169, For Love & Lemons)

A cardigan in the next It Color…
You’re about to see this shade of pink everywhere this spring, so why not get a jump start on the trend? I love how the brand styled this classic cardigan with micro shorts, tights, and heels to dress it up. Plus, it’s made with wool, so you’ll stay warm if you’re bopping from bar to bar. ($168, Reformation)

A heart tennis necklace that looks more expensive than it is…
If you’re going out with the girls, you might as well add a little playfulness to your accessories. This tennis necklace with heart-shaped cubic zirconia makes just the right statement. Add it to your necklace stack whenever you want to show yourself some extra love. ($44.50, J.Crew)
Cozy Night In

The coziest pajama set I’ve ever worn…
I’ve never been a pajama set person...until I got my first Eberjey set for Christma. Not to be dramatic, but it’s changed my life. The fabric is not only incredibly soft, but it also somehow keeps you warm and stays cool at the same time. It might be sorcery, but I’m not asking questions. The little hearts on this set are so sweet. ($158, Anthropologie)

A sweater that feels more put-together than a sweatshirt…
If your plans consist of firing up Love Actually on the small screen in your home, treat yourself to a heart-adorned sweater that’s more fun than pulling on your old college sweatshirt. The bright pink heart pattern will put you in a cheery mood, especially when you pair it with the matching shorts. ($138, Nordstrom)

Joggers that will tell your ex all they need to know…
If you find yourself getting out of a relationship or trying to avoid one that keeps coming back to haunt you, Boys Lie is the brand for you. These joggers feature a sassy saying on the leg that will give you a laugh (and send a message if you post a mirror selfie in them). The matching hoodie is necessary. ($100, Revolve)

A silk sleep shirt you’ll want to live in…
Not only does lounging around in this silk sleep shirt feel incredibly luxurious, but you can also throw it in the washing machine, unlike most silk pieces. It’s the perfect length and comes in a lovely shade of lilac. ($168, Lunya)

Leggings that feel like butter on the skin…
Hot take: Aritzia activewear is better than a lot of activewear brands. These leggings are soft, sweat-wicking, and stay up whether you’re running on the treadmill or to the fridge for another snack. The berry pink is pretty for the occasion, and it has a lot of matching pieces to go with it. ($78, Aritzia)
What to Wear Underneath

A push-up bra that’s actually comfortable…
The push-up bra is having a comeback, and leave it to Kim Kardashian to make one that’s actually enjoyable to wear. It gives you just the right amount of lift while remaining completely seamless under a tight-fitting shirt. It’s a lingerie drawer essential. ($60, Skims)

A triangle bra in a fun print…
I have this bra in black, and I wear it all the time under sheer tops or a blazer. The new heart print screams Valentine’s Day and completes your date night ’fit. Grab the matching underwear to feel put-together with barely anything on. ($108, Fleur du Mal)

A set of comfy lace thongs…
These have a lace waistband and a soft jersey bottom that’s great for those with sensitive skin, or just don’t want to lounge in all-over lace. They have a low-rise fit and won’t show through even the tightest dresses. The set comes with three bright colors. ($69, Nordstrom)
Live Smarter
Sign up for the Daily Skimm email newsletter. Delivered to your inbox every morning and prepares you for your day in minutes.