Deciding on what to wear can be one of the most daunting tasks when it comes to prepping for a first date. One key thing to remember? Comfy pieces are your best friend, because the last thing you want to be thinking about is that off-the-shoulder blouse that won’t stay put. Looking good definitely doesn’t need to equal discontent, and in the end, you’ll want to walk out that door in something that makes you feel the most confident. To help save you some stress, I’ve rounded up seven simple yet heart eye-worthy ways to style your outfits, whether you’re looking to dress up for a night out or go for a more casual, toned-down approach. Keep scrolling for some seriously chic date-night outfit inspiration from our community.
For the Roller Rink
Like I said, the keywords here are comfort and confidence. A trip to the roller rink deserves a cute (but still functional) ensemble to go along with it. For optimal skating moves, put on your coziest sweater and statement denim like these lace-up jeans. Top off the cropped pant look with pink Old Skool Vans, and add frilly socks just for fun.
For the Drive-In
For a chilly night out at the movies, your favorite jeans paired with a simple button-down will do the trick. These versatile pieces leave you with some room to play around with accessories, which is where the real fun starts, as we know. This community member bumped up her look with a classic bandana and a western-inspired belt. And last but not least, she threw on a fuzzy leopard print coat for good measure. It’s easy, effortless, and especially suitable for cuddling purposes.
For the Concert Night
We’re back at it again with the beloved western belt, but a little more dressed up this time. Integrate the double buckle into a bold, monochrome outfit, opting for a distressed denim skirt instead of pants. The winning piece just may be the intergalactic ankle booties, but it’s hard to choose a favorite when everything meshes together so seamlessly. Before you head out the door with those tickets, don’t forget to grab that leather jacket.
For Exploring the City
Whether it’s visiting record stores, going to a bookshop, thrifting for some cool vintage, or all of the above, you’ll want to show up in your best threads that’ll last you the whole day. You can never go wrong with a T-shirt dress, and if it’s velvet and covered with pretty patches like this one? Even better. A good pair of Doc Martens are sure to get you through all that walking as you two lovebirds have your own mini-adventure for the day.
For a Fancy Brunch
If you’ve got yourself a bougie brunch date, use it as a perfect excuse for breaking out the heels. And with just a few solid layering techniques, you can work in some sartorial magic. For a play on texture and silhouette, try a bustier over a metallic button-down.
For a Museum Day
A day looking at pretty art calls for an elegant button-down dress like this little number. It’s like the T-shirt dress’ older sister—sophisticated, and with the slightest yet most beautiful ruffle detailing on the bottom. You can shoot for an olive tone if you’re into earthy hues, or a brighter color if you fancy. It doesn’t get any easier than this.
For a Dinner Date
And finally, we’ve made it to the classic dinner date. Instead of limiting yourself to longer, flowy dresses, consider all your options with a mini. You can take some inspiration from this perfect look with a unique floral pattern and a silhouette reminiscent of the ’60s. We know throwing on a leather jacket can finish off a good look, but who says you can’t wear matching shoes while you’re at it?
Now that you’ve got your outfit decided, try these low-key hairstyles for an effortless date-night look.
Featured photo by @iamthehag.