21 Valentine’s Day Outfit Ideas for Every Type of Date

Valentine’s Day outfits shouldn’t stress you out. Maybe you have reservations at that cute candlelit restaurant downtown or maybe you’re just meeting up for drinks at a low-key bar. Maybe you’re just cuddling up on the couch. Regardless of what you’re doing on Valentine’s Day your outfit can fit the ambiance without you having to stress. I promise you that putting together the right pieces makes you feel better and helps set the mood.

Here are 21 outfits that solve that awkward “what do I wear” scramble while making sure that you’re comfortable and cute no matter what you plan to do on Valentine’s Day.

Casual Pink Striped Shirt with White Wide-Leg Trousers

Say hello to your new Valentine’s Day lunch outfit. This comfy, yet super cute pink striped shirt is perfect to wear whether you’re venturing out for Valentines day lunch or wearing to work.

Add a pair of high-waisted white wide-leg pants and you’re going to look stunning whether you’re going somewhere nice or running errands.

White wide-leg pants are in style this year because the high waist makes your waist look small (hurray!) and the pants naturally flow when you walk. If you’re cold bundle up in a camel colored coat. You’ll stay warm and still show off your outfit.

Try to grab a shirt that’s slightly oversized. They’re way easier to tuck into your pants and they always look more flattering. Also you won’t feel as suffocated when you’re burrying your face in cake at lunch. Trust me, the extra room is worth it.

I love this whole look because it’s super simple, but still looks like you put in effort. And that’s honestly the best kind of outfit.

Elegant Black Ruched Mini Dress with Brown Woven Clutch

Who’s ready to kill their Valentine’s Day night out ? Pair this black ruched mini dress with some sheerrtights for an outfit that will blow your date away. The dress fits snug in all the right places, but the tights will keep you warm plus add some mystery.

Add a brown woven clutch and you have yourself some chic earthy contrast that takes the formality out of the outfit.

The great thing about this outfit is that you could wear it virtually anywhere. Whether your going to an upscale restaurant or a cute wine bar you’ll look adorable. Feeling a littledressy? Don’t sweat it! Just keep a fitted blazer on hand that you can throw over your shoulders when you need to tone it down.

Bonus: Department stores usually carry cute pieces like this all year round. So you don’t have to just dump it after Valentine’s Day because you wasted money, you can wear it whenever you want.

Oversized Brown Suede Bomber Jacket with Black Mini Skirt

Who doesn’t love getting oversized hugs? Now you can pretend your loved one is giving you a big cuddle while STILL looking fantastic with this oversized brown suede bomber.

Pair it with a black mini skirt and knee-high boots for that cozy, hot look that’s perfect whether you’re going out to dinner or meeting up with girlfriends. I love adding an animal print clutch to complete the look. It ties everything together but isn’t overbearing. 

Layers are lifesavers when your chilling outside in February. If your cold-hearted like me throw on some black sheer tights under your skirt. They’ll keep you warm and you’ll still look sexy and put together. Also suede can be tricky to maintain. If you’re worried about ruining it in the rain on Valentine’s Day (or you just dont want that extra responsibility) grab a faux suede jacket instead. It’s basically the same thing and no one will know the difference.

Classic White Button-Down Shirt with Light Wash Relaxed Jeans

Pair this flattering white button-up shirt with some light-washed relaxed jeans and you have yourself a cute outfit that you’ll feel comfortable throwing together whether your going to dinner or just meeting up for drinks.

Heels really dress up this whole look (even though youre technically wearing jeans haha), and a classic black bag really pulls everything together.

Pro tip: buy a shirt that’s slightly oversized and only tuck the front half into your pants. You’ll look 100x better than if you just tucked it all the way in trust me.

Oh and layers! If its cold where you live in February just throw on a thin sweater or cardigan over your shirt. You can always take it off once you get there and won’t be freezing on your way to dinner. A lot of restaurants are way warmer than you’d think, so layers are key.

Honestly half the items you need for this outfit you probably already have in your closet. Just make sure your jeans aren’t overly baggy and that your shirt is actually clean lol.

Burgundy Turtleneck with Black Faux-Leather Skater Skirt

Whoever said Valentine’s Day outfits had to be red is dead wrong. Try throwing on a burgundy turtleneck tucked into a black skater skirt for a mix of professional and playful.

The deep wine color is extremely flattering on pretty much every skin tone and is romantic without being too sappy like regular red. Pair it with black tights and ankle boots if your cold. You’ll stay warm and still be cute as heck.

I love skater skirts because of how it flows when you walk. It creates this sexy, flirtatious figure that’s perfect for a night out with your sweetheart but you won’t feel over dressed. It’s such a simple outfit that looks like you put effort into it.

I know you probably already have some form of these items in your closet. A burgundy top and black skirt are basic staples that can be worn for nearly any occasion. So you get tons of uses out of this outfit.

White Cami Top with Pink Swirl Print Maxi Skirt

This cute white cami paired with a pink swirl skirt is adorable for maybe switching into afternoon drinks after a lunch date. The light material is perfect if your dining room gets too hot inside and the girly print means you don’t need to overload on accessories. Some pearl earrings or a thin chain necklace would be perfect with this.

If it starts getting chilly you can always add a thin cropped sweater in white or light pink instead of a heavy coat that will hide your outfit. Pro-tip: look for a cami with adjustable straps that way you can make it fit just how you like it. Best for dancing and flitting around after dinner.

Polka Dot Mesh Top with Button-Front Denim Mini Skirt

If your going low-key you can’t go wrong with this cute sheer polka dot top over a basic cami and jeans. I love the button front denim mini skirt because it’s flattering and this whole outfit can go practically anywhere – dinner, drinks, whatever you have planned.

The mesh top adds some fun texture but won’t give too much skin. And denim dresses down the whole look and allows you to move freely. If you end up somewhere chilly add some thick tights and consider a cropped cardigan you can remove later when you warm up inside.

Don’t be basic – throw on black polka dots everyone else will be wearing. Instead try fun colors like burgundy or deep blue dots. It’s unexpected and will make your outfit look more put together. Not to mention you can re-wear both of these pieces with other items you own making it a super practical buy.

White Lace Long-Sleeve Sheath Dress

White lace is the perfect inbetween material to wear on Valentine’s Day. You’re probably running from work to meet your sweetie but you still want to look like you made an effort, am I right?

Great thing about this look is you don’t need to overload on jewelry. Some simple gold necklaces and youre ready to go. The lace adds romance without overdoing it, and the sheath style flatters pretty much everyone.

If you get cold later on just throw on a cropped cardigan or blazer. Pro-tip: try and find a dress with some stretch to the material. Trust me on this you’ll be comfortable whether you’re stuffing your face with desserts or dancing post dinner.

Heart-Embroidered Cable Knit Cardigan with White Pleated Skirt

This outfit is adorable and doesn’t try too hard. You’re basically layering a heart embroidered cardigan over a regular t-shirt and throwing on a pleated skirt. The pleated skirt is so cute because it flows as you walk.

It’s cute enough for a Valentine’s Day coffee date when you want to look nice but not too dressy. It’s also cute enough to wear to work if you’re trekking out to dinner later. The heart cardigan will keep you warm since February can be pretty chilly and the skirt keeps the whole vibe feminine.

If you work somewhere that’s chilly indoors you should 100% wear flesh colored tights. They elongate your legs and keep you warm – what’s not to love? Places always have their studs out around Valentine’s so you can find some cute vintage inspired heart embroidered cardigans at your local thrift store. That way you don’t spend money you probably don’t have on something you might not wear again.

Beige Cropped Blazer and Top with Ripped Skinny Jeans

This whole outfit is ideal for grabbing coffee or going to a low-key dinner with your loved one. The beige cropped blazer looks sharp without trying too hard. The nude top underneath keeps the whole vibe relaxed. And who doesn’t love some good ole ripped jeans? It adds some edge and shows off your personality.

This would be perfect if your running out of work to meet up with your special someone. You can even swap out jewelry depending on the vibe you’re going for. Keep it sweet with some dainty necklaces or go bolder with a pair of fun earrings.

If you start getting chilly you’re covered with the blazer. You won’t have to worry about dragging around a heavy winter coat all night.

Make sure to get a pair of high-waisted ripped jeans when you’re shopping for this blazer. Because the blazer is cropped high-waisted jeans are extremely flattering with this look. Trust me you’ll notice a difference. 

Red Polka Dot Ruffle Top and Cardigan with Blue Jeans

This is another casual outfit that’s perfect if your not trying to break a sweat. Red polka dot ruffle top has subtle Valentine’s Day vibes but you can totally wear it long after February.

Pair it with your favorite jeans and thats it! You’re comfortable but still look cute enough. It’s perfect for a casual dinner date or even a night out with the girls (they will probs make fun of you for being festive but oh well.)

The cardigan is my favorite part. You’ll be able to throw it on if it’s cold outside but then take it off if your restaurant has no heat and you’re freezing. Lets be real thats probs what’s going to happen. But layering with a cardigan doesn’t mess up the look.

Keep in mind when you’re shopping for this cute top that not all ruffle details are made cute. Some are super extra and that’s not what we’re going for with this look. Also try and find a cropped cardigan so people can see your cute top underneath. What’s the point of wearing a cute shirt if no one can see it.

Vibrant Red Bow-Accent Tube Top with Black Wide-Leg Trousers

Red bow accent tube tops are absolutely adorable for Valentine’s Day and pair really well with black wide-leg pants. You’ll feel fancy enough to go to that nice dinner you’ve been busting your butt at work for, but won’t feel over dressed if you decide to go somewhere more low-key.

If your cold I definitely suggest throwing on a cropped cardigan. It’s January/February in most places so trust me on that one. Pro-tip when your shopping for this top if you’re nervous about it slipping make sure you buy some fashion tape. I always use it on the top edge and it keeps any cute top up. No one wants to spend their Valentine’s worried about their top falling down.

Black wide-leg pants are the perfect counterpart to a fitted top. It gives you that elegant vibe and boy are they comfortable. You won’t regret wearing these all night long.

Cream Ribbed Button-Up Top with Brown Tailored Mini Skirt

If your looking to be cute and put together this Valentine’s Day I got your solution. Simply grab a fitted cream button-up and pair it with a cute brown mini skirt. It’s so simple, yet you’ll look amazing whether your going out to dinner or just meeting up with your S.O. for coffee. 

I love the neutral colors of this look because you can really pair anything with these colors, and the fitted style is flattering but not too over the top. You don’t want to look like your trying too hard….

My favorite part? THE BOOTS. Whether you’re rocking some chunky booties or cute knee-high boots it dresses up the whole outfit. Not to mention you won’t be dying by the end of the night because your feet hurt.

Similar to my first outfit if you start getting chilly you can always throw on a cropped cardigan or even an oversized blazer. You’ll look cute af trust me. Layers don’t ruin the outfit. 

Pink Denim Utility Mini Dress

If your looking for a comfortable outfit that’ll make you feel cute and stylish you have to try the pink denim mini dress. Not only will it feel like you’re wearing your favorite pair of jeans, but it also gives you that pop of color we all love to celebrate the occasion.

Complete your look with the adorable dog purse to let your personality shine through without trying too hard. Whether your brunching with friends or on a casual date with your special someone this outfit is perfect for breaking the balance between cute and put together.

Pair with white sneakers for a daytime look or throw on ankle boots when its too chilly later that night. Did I mention denim is okay with you eating all that Valentine’s Day chocolate? Win win.

White Ribbed Halter Crop Top with Pink Flare Jeans

While there’s nothing wrong with going full force on Valentine’s Day with heart-patterned clothing and tons of lace, sometimes it’s better to play it cute and simple. White halter crop top paired with pink flare jeans is the perfect balance between festive and functional, especially if you’re doing something simple like a day date or brunch with friends. Pair the outfit with sneakers to keep comfy when walking between places or dancing later on down the line, and keep accessories minimal so nothing gets in the way.

If you’re like me and February weather is always predicting one thing and completely surprises you with another, I would suggest keeping a lightweight white denim jacket on hand. You can tie it around your waste until you actually need it, and throw it on when you get chilly. When picking out your flare jeans, make sure you’re getting a high-waisted pair to go along with your crop top.

Bright Pink Knit Sweater with White Linen Shorts

If the weather starts heating up during spring but its still cool in the mornings, grab a bright pink knit sweater and pair it with white linen shorts. This outfit is perfect for a weekend brunch with friends or even wearing to work on casual Fridays when you want to look cute without trying too hard.

Not only will you be glowing from how good the bright pink makes you feel, you’ll get tons of compliments too. The white shorts also help keep your outfit feeling light and Spring-y. If you work at a more professional office, try switching out the shorts for white pants. Same colors, but a lot more office appropriate.

Here’s a little styling tip: Try picking out a knit sweater that’s slightly oversized, and half tuck it into some high-waisted shorts. This helps accentuate your waist, and makes your whole outfit look so put together. Trust me, the half tuck is life-changing.

Red Off-The-Shoulder Bodysuit with Black Flare Trousers

This next outfit is sure to make a statement on Valentine’s Day. Red off-shoulder bodysuit and black flare trousers is SUCH a great mix of sexy and chic.

Whether you’re planning on going to dinner then finding somewhere to dance after, or both; ALOT of girls are really loving this look. Not only does it look ah-mazing for pictures (instagram anyone?) but it’s also super comfortable to wear all night long.

A helpful styling tip if you’re worried about the bodysuit sliding down is to buy one with those silicone grip strips on the shoulders. It helps keep everything in place and you won’t have to constantly adjust yourself.

When matching your shoes and bag to your outfit, you don’t want to stress too much about them being exact matching shades of red. In fact, it actually looks more natural if they’re just similar. No ones going to notice if one color is slightly brighter than the other.

Its such a confident look that doesn’t even seem like you tried hard.

Elegant Pink Off-The-Shoulder Midi Dress with Taupe Clutch

Trust me on this one. Get yourself a silky pink dress. It’s perfect for Valentine’s dinner because you’re nice and dressed up, without being over dressed. Not only will you look SO put together, you’ll feel that way too. Dresses that have this kind of material flow so nicely when you walk.

I would pair this dress with a taupe clutch to keep the whole look elegant, yet not matchy-matchy. Here’s another bonus- you can literally wear this dress to work, then straight to your date spot without changing.

Keep in mind though, silk doesn’t keep you very warm. If you know its going to be cold at night grab a cardigan or blazer to layer on top. Trust me, your outfit will still look good.

Pro tip: buy a taupe clutch. They go with EVERYTHING in your closet. Its not just a Valentine’s Day clutch, you can wear it all year round which makes it worth the purchase. Neutral colors are SO easy to style than brighter colors.

Black Corset-Style Maxi Dress

A black corset-style dress is also another great pick for Valentine’s dinner. Not only will you look INCREDIBLE, but you won’t feel like you can’t eat because your dress is telling you no.

The structured top half of the dress helps give you great shape, while the longer flowy skirt keeps the whole look classy without revealing too much skin. If you’re cold in February like me, pair this dress with a cropped cardigan or fitted jacket. Just try not to wear anything that’ll hide the corset part of the dress, because that’s the whole focal point!

Want the whole look to be less fancy? Wear cute flat ankle boots instead of heels, and keep your jewelry minimal. A simple pendant necklace will do the trick and bring attention to your neckline without fighting with your dress.

Pro tip: Many corset style dresses now include stretchy panels on the sides. This will allow you to breathe and not feel compressed at your sides. Enjoy your dinner and your dessert without worrying about feeling like you ate too much.

Bold Red Tailored Power Suit

Want to switch up Valentine’s Day vibes and go for something a little more bold and powerful? Throw on a red suit. If you’re wanting to stand out from the sea of girls wearing cute date night dresses; this tailored red power suit is going to give you that sophisticated edge we all love.

Having both pieces be the same color makes you look taller, and since its red its perfect for the occasion without looking like a witch costume.

Keep your accessories simple and minimal so your suit can make a statement. Maybe a little gold jewelry, and some nude heels. That’s it. If you don’t want to commit to an all red outfit, you can always separate the pieces. Wear the red blazer with black pants, or the red pants with a plain white button up shirt. That way you can reuse them for other occasions besides Valentine’s Day.

Cream Heart-Pattern Knit Sweater with Light Wash Blue Jeans

Want something that screams Valentine’s Day, without literally screaming? Throw on a cream heart-knit sweater and light wash blue jeans. Perfect for running around the city when its cold out, or even a cute coffee date.

I would complete this look with some boots to bring the whole outfit together while still keeping you comfy. Tip: If you choose a sweater that’s really chunky, you should wear skinny jeans to avoid looking bulky everywhere.

I tend to stay away from heart patterns because sometimes they can be childish, BUT when they’re small and in neutral colors they’re super cute and sophisticated. This whole outfit gives me cozy meets cute vibes. Exactly what we’re going for.