February 11, 2025
Valentine’s Outfit Ideas: Casual, Chic and Everything In-Between
What better excuse to get dressed up than for Valentine’s Day? Whether you’re planning on spending the day with your partner, getting quality time with family or celebrating with your gals, nothing beats a special occasion that celebrates the love you share. From chic and sophisticated to playful and casual, creating that perfect look can play a big part in making your night unforgettable.
Choosing what to wear on Valentine’s Day is all about curating looks that make you feel confident and comfortable. From cozy cardigans and sweater dresses to red and pink everything, we’ve got ideas to help you put together the perfect look for whatever you’ve got planned.
Keep scrolling to see 10 of our favorite Valentine’s day night outfit recommendations, plus a few do’s and don’ts to keep in mind while choosing your look.
1. Pink Dress With Wedge Sandals
We know — pink on Valentine’s Day might not feel like the most unique choice, but hear us out. An understated pink dress, minimalist gold accessories and a pair of wedge sandals is a great way to keep it fun and stylish without feeling Valentine’s cheesy.
Your options are wide open when it comes to the dress. If you’re feeling romantic, go with something soft and flowy. For a more casual vibe, a simple slip dress works perfectly. The best part? Wedge sandals pair perfectly with all of these, giving you all-night height and comfort.
2. Midi Skirt With Leather Booties
Pink and red are classic V-Day colors, but they’re far from your only options. If you’re looking for cute Valentine’s day outfits with a little edge and personality, a midi skirt with leather booties checks all the boxes.
Some color combinations we love include soft neutrals like cream and tan or rich tones like burgundy and forest green. Leather booties anchor the look and give it just enough attitude, while the midi skirt softens the look for a romantic yet trendy look.
3. White Romper With Floral Sneakers
You don’t have to go out and buy new Valentine’s day clothing to put together a great outfit. A white romper might feel like a summer staple, but it’s a great choice for Valentine’s Day. It’s fresh and fun and with just a little styling, like a cute pair of floral sneakers and some statement jewelry in silver or gold, you can elevate it from summer casual to chic elegance.
Rompers are great for daytime plans, like a coffee date or a romantic picnic, and floral sneakers are a cute way to add a little charm without overcomplicating things.
4. Corset Top With Textile Booties
Want a little drama this Valentine’s Day? A corset top with textile booties is a bold yet casual Valentine’s Day outfit. This combo works for a night out where you want to bring a little extra something to the table. Balance the top with high-waisted trousers or a midi skirt to keep it classy but fun, and tie the look together with a pair of booties to keep you warm and comfortable all night long.
Add a statement necklace or chunky earrings to elevate the look even further. Finish with a sleek clutch or a mini handbag to keep your essentials stylishly on hand
5. Cardigan and Chelsea Boots
Not all Valentine’s Day plans call for dressing to the nines. For those laid-back days or when you’re putting together something cozy for staying in, a cardigan paired with Chelsea boots keeps it stylish and comfortable. Plus, it’s a great option for Valentine’s Day family outfits where you want to spend an evening celebrating with your clan.
An oversized cardigan with jeans is the perfect daytime outfit, and, for something a little dressier, a fitted cardigan over a simple dress is the perfect combination between edgy and delicate. Chelsea boots add that practical, functional element while still keeping things elegant enough for the occasion.
6. Sweater Dress With Platform Espadrilles
If you’re lucky enough to spend Valentine’s Day somewhere warm, a sweater dress with platform espadrilles is a great way to keep it festive, stylish and weather-appropriate. It’s an easy outfit for outdoor brunches, daytime dates or a sunset stroll along the beach. Keep it simple with neutral tones or play it up with a pop of color, like pink or red.
Accessorize with a woven tote bag and delicate gold jewelry for a chic, effortless vibe. For a little extra flair, add a wide-brim hat or oversized sunglasses to complete the look.
7. Black Dress With White Sneakers
If you’re not into traditional Valentine’s Day colors but still want to give a subtle nod to the romance of the day, a little black dress is always a good choice. The LBD is timeless, versatile and works for so many occasions. Plus, you can dress it down with white sneakers for a modern and casual Valentine’s Day outfit.
This combo opens up a world of possibilities for Valentine's date night outfits! But you’re not limited to romantic dinner dates or movie nights — it’s perfect for anything from a museum date to exploring the city or catching a movie. Wear it with gold or silver jewelry and pair it with red lipstick to amp up Valentine’s Day vibes.
8. Lace Top with A-Line Skirt and Flats
Looking for romantic Valentine’s outfit ideas that are both feminine and comfortable? You can’t go wrong with a lace top, a cute skirt and a pair of flats. This look is a classic that feels thoughtful without trying too hard, perfect for anything from lunch to a relaxed evening out.
Stick to soft colors for a more delicate moment or choose bold tones, like bright red, if you want to turn heads. Add a dainty pendant necklace or pearl earrings for a little extra elegance and finish with a structured handbag or a crossbody purse.
9. Off-the-Shoulder Top with High-Waisted Jeans and Mules
Who says you can’t wear your favorite jeans for Valentine’s date night? Whether you’re catching a movie with your significant other or celebrating with friends, a flowy off-the-shoulder top with high-waisted jeans and mules creates a stylish Valentine’s Day outfit that works for both day and night.
The off-the-shoulder top is both romantic and elegant, and the mules elevate the look just enough to make it feel like a special occasion. With a nice bag and dainty jewelry, you’ll have a comfortable, versatile and fashionable outfit that’s appropriate for whatever plans you’ve got lined up.
10. Plaid Skirt with Turtleneck and Loafers
Preppy looks are always in style, and Valentine’s Day is a great excuse to embrace it. A plaid skirt with a fitted turtleneck and loafers feels classic, elevated, and stylish. Since Valentine’s Day is a winter holiday for many of us, wearing a turtleneck helps keep things warm and cozy, while the plaid skirt (bonus points for tights) adds a unique twist.
This look works for anything from work events to brunch to dinner. Accessorize with gold hoop earrings and layer on a tailored coat or a chic blazer to tie everything together.
The Do’s and Don’ts of Creating a Valentine’s Day Look
While there’s no hard and fast rule about what you can and cannot wear on V-Day, leaning into Valentine’s fashion is a fun way to embrace the day and make your outfit feel a little more special.
Here are a few quick tips to help you put together a look you’ll love:
Do’s
- Incorporate red, pink or heart-inspired details
- Dress for the occasion and your plans
- Choose comfortable shoes that fit the outfit
- Have fun with romantic textures like lace, velvet or satin
- Play with subtle Valentine’s patterns, like hearts or florals
- Layer thoughtfully if your plans include outdoor activities
- Pick outfits that reflect your personality — this is your day to shine!
- Have fun layering jewelry, like rings or necklaces, to add a unique, trendy touch
Don’ts
- Overdo it with too many Valentine’s-themed elements at once
- Forget to factor in the weather when planning your outfit
- Force a trend that doesn’t go with your style or feels unnatural
- Ignore comfort — there’s nothing cute about being uncomfortable!
- Wait until the last minute to decide what to wear
- Go for something overly complicated that will leave you adjusting all night
- Rely too heavily on one color unless you’re going for a monochromatic look
- Overlook the little details, like well-groomed nails or a chic hair style
Wear TOMS. Wear Good.
Whether you're a Valentine’s enthusiast or just looking for an excuse to dress up, figuring out what to wear can be half the fun! Valentine’s Day is the perfect moment to lean into your style — whether that’s casual and cool, dressed-up and romantic or something in between.
Once you’ve got the outfit down, finding the perfect shoes is easy with TOMS. Check out our Valentine’s Day collection to find the perfect look. Our shoes don’t just look great — they’re also a choice you can feel good about. Every pair you choose helps make a difference in communities around the world. Learn more about our impact.
Explore our women’s shoe collection and find the perfect pair to celebrate in style!