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13 Casual Date Night Outfits That’ll Keep You Looking Hot and Feeling Good

Casual Date Night Outfits

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.

Blazer

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.  

Casual Summer Date Night Outfits

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. 

Casual Winter Date Night Outfits

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.

Sweater

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.

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