13 Casual Date Night Outfits That'll Keep You Looking Hot and Feeling Good (2024)

13 Casual Date Night Outfits That'll Keep You Looking Hot and Feeling Good (1)

13 Casual Date Night Outfits That'll Keep You Looking Hot and Feeling Good (2)

We love a date night.

Whether it’s a friend date with your bestie, a first date, or your millionth date with your husband, there’s something special about going out just to spend time together (without phones or distractions).

It can be the perfect opportunity to get to know someone new, or a fun chance to appreciate someone you already know you’re obsessed with.

It’s also a great chance to flaunt what you’ve got aka style, class, and a killer skincare routine.

But for some people, deciding what to wear can be a little stressful. Like, not fun at all. And that’s not what date night is about.

There’s a lot to consider: the occasion, the dress code, the temperature, what your date will be wearing, the height of your heels, the color of your lipstick… it can be a lot.

That’s why today, we want to make it easy on you. Sit back, relax and get into that date-night mood with our round-up of outfit ideas that will make you look chic and confident, while feeling comfortable at the same time.

13 Casual Date Night Outfits

Casual Spring Date Night Outfits

Spring Jacket

In the spring, you’ve got to be ready for a quick change in weather. You never know when a spring storm might come by. So if you’re taking a fun little walk in the park, make sure you’ve got a jacket with you, like this Loro Piana jacket Lauryn loves.

Pair it with a simple white turtleneck and your favorite pair of ripped jeans and you’re ready to smell the roses.

HOT TIP: Bring your sunglasses too. They spruce up any outfit and protect your eyes.

Trench Coat

We just love trench coats right now. Burberry has so many new ones out and we love this one by Khaite. The best thing about a trench is it makes you look chic even if you’re wearing leggings and sneakers. Grab Lauryn’s favorite leggings, an oversize button-up , sneakers, and your trench coat for an easy breezy, but chic, casual date.

Spring Dress

Staying in but still want to look like an absolute goddess? Same. That’s why we’re so glad they invented lounge dresses. They’re romantic and sexy, perfect for steaming up a date night in.

Be sure to prep with your Butter Brush and Le Spoon… you’ll want that skin feeling buttery-soft.


There’s nothing that makes a statement quite like a blazer.

Wear an oversized blazer with a fitted pair of jeans and a sweater to keep you warm or just a basic tee if it’s already nice out.

13 Casual Date Night Outfits That'll Keep You Looking Hot and Feeling Good (3)

Casual Summer Date Night Outfits

Sun Dress

Summer Sunday brunch date? Say less. You know we’re there, and we’ll be there in our Sunday best.

This baby blue dress is exactly what we want. Fun, sexy, but sweet and chic too. It’s giving major Madison LeCroy vibes and we’re all about it. Remember your SPF, obnoxious visor and driving gloves if you’re hitting the patio.

Shorts, Tank, Hat

Think Topgolf date, walk in the park, summer afternoon type vibes. The reason we love shorts, tank, and hat outfits is that they’re so versatile even just changing one of the pieces can totally change your look, like changing your baseball cap to a sun hat.

Button-down & Shorts

The button-down is a good way to stay cool in the summer while also protecting your skin. Keep those arms in the shade with this oversize Oxford shirt and fun shorts. Feel free to tuck in the front of your shirt or just the side for a cool French girl look or wear it open with a tight white tank underneath.

While you’re trying not to bake in the summer heat, you might need some help staying cool. The The Skinny Confidential ice roller and Depuffing oil are a powerful duo for keeping you cool, firm, and sculpted.

Casual Fall Date Night Outfits

Little Black Dress

A little black dress is ALWAYS going to be a yes from us for a casual date outfit. It’s a classic, and for good reason. It’s a good look on literally everyone.

To rock this look: pair an LBD with an oversized blazer or leather jacket of your choice.

Elevate Athleisure

An athletic jumpsuit is super on trend, while still being put together and sexy. And if you want to cover up a little try an oversized button-up or flannel tied around your waist or worn open.

Wide-Leg Pants

Wide-leg pants extend the line of your silhouette, drawing the eye to the length of your legs. And with wide-leg pants, you’ve got legs for days.

Lauryn loves these high-rise wide-leg jeans, and we love them for date night, too. Pair them with a fitted turtleneck and virtually any jacket.

13 Casual Date Night Outfits That'll Keep You Looking Hot and Feeling Good (4)

Casual Winter Date Night Outfits

Sweater Dress

Going for super comfy, low-effort, but high performance? Winter dates can make it hard to find that balance. Try a sweater dress. They’re cozy while giving off all the winter-y vibes.

You can change your look a lot by changing your shoes. Try ankle or mid calf boots or sneakers.


Try black dress pants (on the slimmer side) with a big cardigan. It’s a perfect casual but very put together look.

Leather Jacket

Date nights are the perfect opportunity to bust out the leather jacket you’ve been dying to wear. It’s a versatile piece and you can get a lot of good outfits out of a leather jacket.

Slay the date in an LBD, your leather jacket, and a pair of heels. Or rock a more casual winter date night with your leather jacket, a basic tee, and a pair of jeans.

Dressing for date night doesn’t have to be stressful make it fun with these easy, comfortable outfits.

Because if you want to look good, the most important piece of your outfit is that you FEEL good, too.

What are your go-to date night staples? Let us know below. For more outfit ideas head over to Lauryn’s LTK page where you can shop all her looks, skincare and wellness favorites. Plus, we just posted our favorite trench coats for Spring, and the cutest sets you have to pack for Spring Break.

x, The Skinny Confidential team

+ Closet edit: learn how to edit, purge and organize.

++ Check out these classic outfits with a twist.


13 Casual Date Night Outfits That'll Keep You Looking Hot and Feeling Good (5)

13 Casual Date Night Outfits That'll Keep You Looking Hot and Feeling Good (2024)


What do you wear on a casual date night? ›

"Keeping it low-key is the main focus." As jeans are practically the definition of casual, they're an ideal choice. "Light-wash, high-waist denim with a T-shirt is a great look and also very classic," Priyanka notes. She suggests styling with a striped cardigan or bomber-style jacket depending on the weather.

How do you put together a date night outfit? ›

Just as classic as a skirt and heels, a dress and boots create the perfect date night outfit for any time of year. If you're heading out to dinner, layer a sweater or cardigan on top and consider a pair of tights, depending on the weather.

What do you wear on a date night stay at home? ›

Dress in your favorite dress and heels for this date night, or keep it casual in denim and a sweater. Meet somewhere in the middle and wear a midi skirt with a soft sweater for your wine tasting or spring's must-have, a cropped jumpsuit.

What should I wear on a date in my 40s? ›

For women, go with a little black dress or a casual blouse and jeans finished with feminine accessories and a natural makeup look. Stick to solid colors or small-scale prints and avoid anything with loud patterns and obnoxious colors that may distract your date.

What should a woman wear on a casual first date over 50? ›

A silk blouse or a V-neck sweater with low heels or pointy flats looks feminine and polished; a simple white T-shirt or crisp white shirt with sleeves turned up and rolled with leather ankle boots looks classy and classic. White jeans with a black blouse or sweater and your black belt are always memorable.

What color is best for a date night? ›

There is something sexy about a red dress that makes it the #1 choice to wear on date night. Regardless of fashion trends, a red dress is always in style. You will always find a dress in this hue at any major retailer, making it a winner every time. A black dress is also a great option.

How do you look seductive on a date? ›

They find it sexiest when you're wearing something that's sophisticated, beautiful and fits your body well without showing too much skin. For example, a black dress with a modest front and an open back, or a silky blouse with a lace camisole peeking through.

What should date night look like? ›

A date night is an occasion where a couple dedicates time to be spent together, usually alone, with the purpose of reconnecting and bonding. A date night usually consists of a main activity, such as a dinner and/or a movie, or a few activities planned one after the other.

What do girls usually wear at night? ›

While we don't know many women who would willingly wear a bra to sleep, some of the most common clothing items worn to bed by the ladies are underpants, socks and even undershirts. The main effect undergarments have on sleep has to do with temperature regulation.

What to wear when he comes over? ›

As a general rule, balance out your silhouette by pairing a tighter top with looser jeans or an oversized top with fitted bottoms. Slide into skinny jeans and a cropped hoodie if you want to show a little more skin.

What should I wear to a night out with my husband? ›

This is a personal preference, but typically something nice and comfortable. Depending on the occasion, you could wear a dress, skirt, slacks, or jeans with a nice shirt or blouse. Make sure you feel confident and comfortable in whatever you choose.

What does a 40 year old woman wear on a night out? ›

Make it a statement top, like the one-shoulder sequin top I'm wearing in the main pic, add some stand-out accessories and you'll be the coolest belle of the ball. The jeans should be your most comfortable; skinnies, cropped or boyfriend style. Just add a pair of heels or sparkly flats and some eye-catching jewellery.

What looks good on 40 year old woman? ›

Invest in high-quality basics like well-fitting jeans, crisp white t-shirts, and classic blazers. Experiment with bold prints, bright colors, and trendy accessories to add interest to your outfits. Try mixing and matching different textures and fabrics to create unique and personalized looks.

What does it mean when a guy wants to match clothes with you? ›

Wearing matching clothes, or clothes that just coordinate with each other shows that the couple has been together for a long time and that their relationship has allowed them to be themselves comfortably while still remaining unified. Plus, couples who coordinate their outfits show that they're on the same page.

What does a casual date look like? ›

Casual dating implies a relaxed and not serious relationship, where two people spend time together, sometimes going on dates and prioritizing physical intimacy. College students and people using dating apps often engage in casual relationships.

What should I wear on a casual dinner date? ›

Casual Ensemble: Casualwear allows for comfortable T-shirts, jeans, and sneakers, but you can upgrade the look with a jacket or overshirt.

What is considered casual date? ›

Casual dating or a casual relationship is a physical and emotional relationship between two people who may have casual sex or a near-sexual relationship without necessarily demanding or expecting the additional commitments of a more formal romantic relationship.

Can you kiss on a casual date? ›

As long as you both want to kiss, it doesn't matter when you do it. You may feel comfortable kissing on a first date, but remember that your date may not be, so assume nothing, and don't feel bad if they're not up for it. They may feel more comfortable after you've gone out a few times!

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