4 First Date Outfit Ideas For All Kinds Of Outings

by Taylor Borde

4 First Date Outfit Ideas For All Kinds Of Outings

You landed the date, now you have to figure out what to wear. Grabbing drinks or going hiking—we’ve got you covered with an outfit for every type first-date activity. Get ready to make a stunning first impression.


The sheer stress of simply going on a first date is enough to overwhelm. Now throw in the question of what to wear. Where does one even begin? We’ve all been there at least once or twice.


Put your worries aside. We’ve got you covered on the outfit front with four editor-approved first date outfit looks that are sure to wow. Grabbing drinks after work, dinner on the weekend, or spending the day with Mother Nature—whatever your romantic vice—scroll below for stylish inspiration that’ll get you feeling like your most beautiful, confident self, whatever the occasion.


1. Flirting Over Cocktails

Cocktail happy hour is a casual setting to get to know your most recent crush. Don’t over-do it with something too fancy. Stick to something you’re comfortable in, like your go-to jeans and a simple, black top that shows a little skin. We’re particularly in love with the pretty ruffles and flattering ruching of this Reformation tank. Chunky-heeled sandals and a small, textured crossbody will add the perfect finishing touches.



Get It! Clockwise from top left: Levi’s jeans, $98; Reformation top, $98; Mango necklace, $30; Topshop heels, $80; Estee & Lilly crossbody bag, $33 $23


2. Sit-Down Dinner


A romantic dinner calls for something a little more sophisticated. Opt for a silhouette that’ll keep you cool and confident all the way through dessert. A flirty print or vibrant color is a fun way to show off your personality. Pair with white heeled mules (stay away from stilettos) and some bold earrings.



Get It! Clockwise from top left: H&M scrunchie, $4; Tobi dress, $72 $36; Baublebar earrings, $34; River Island mules, $64; Zara crossbody bag, $50


3. Casual Movie Date


For a relaxed and casual movie date, forgo vintage Levi’s for bottoms with a bit more room to move (i.e. nothing 100 percent cotton). A long wrap skirt is always a good staple to start with because you’re automatically comfortable and the style is universally flattering. Tie up or tuck in a graphic tee for a cool girl look that can’t go wrong. We’re loving this first date outfit with a cropped moto jacket to keep cozy in a chilly theatre.




Get It! Clockwise from top left: & Other Stories skirt, $69; Urban Outfitters tank, $39; Staud mini tote, $196; Topshop moto jacket, $88 $59; Forever 21 sandals, $20


4. Hitting the Trails


More of an outdoorsy type? Be prepared for anything Mother Nature could throw at you with an outfit that’s equal parts cute and comfy. Show off your sporty side with a fun sports bra and high-waisted athletic leggings paired with sneakers you’re not afraid to get dirty. Throw a chic baseball cap and lightweight jacket in your carry-all so you can focus on your cute date instead of the weather.



Get It! Clockwise from top left: Madewell hat, $30; Beyond Yoga sports bra, $65; Old Navy leggings, $33 $20; Adidas sneakers, $85; Kendall + Kylie backpack, $80