Have a date coming up? There’s something really exciting about getting ready for a planned occasion with that special someone. Of course, a big part of that is deciding what to wear. You want your date outfit to check a lot of boxes: It needs to make you feel like your most confident and gorgeous self, it needs to match the vibe of the date destination, and, if it’s a first date, there’s first impression jitters to contend with, too.
Not to worry. Our expert team of Stitch Fix Stylists are (always) here to help! They’re chock-full of experience in picking out the perfect date night outfit for any occasion.
Whether you’re on that first date, a special Valentine’s Day outing or out for the hundredth-something time with your significant other, our comprehensive go-to guide of what to wear has got you covered. This way, you’ll know exactly what to wear on a date night, no matter the venue.
Let’s get into it! Here’s our list of 6 date night outfits for any and every outing.
Romantic Dinner Reservation
Excited to try out the new town hot spot? Or thrilled to hit up your sweet little go-to—you know, the one where you’re greeted with: “The usual?” No matter where the plan takes you, a dinner reservation is the perfect time to debut that new piece you’ve been dying to wear.
Stylist Michelle’s favorite dinner date outfit: “A sleek dress with statement earrings or heels—it’s a timeless look.” You really can never go wrong with a great one-and-done dress. Try out a fun color or pattern, or, when in doubt, a LBD (little black dress) is a classic. Not into dresses? No prob. A sleek bodysuit and trousers combo is a date-worthy option, too.
Accessorizing is just as important as ordering right. “Elevate your look with thoughtful details that feel authentically you,” says Stylist Michelle. Make a statement with accents like animal-print or sparkling shoes, faux leather jackets, bold earrings or a chic little bag. Then you’re all set. And remember, getting dessert is a non-negotiable.
“Elevate your look with thoughtful details that feel authentically you” -Michelle, Stylist
Date Day
Who says dates are only for nighttime? Coffee and brunch dates are absolutely underrated. For your daytime rendez-vous, Stylist Michelle suggests, “Go for a midi skirt with sneakers for an easy yet stylish outfit.”
In our opinion, the midi skirt is as underrated as a day date. And, it’s so easy to dress up or down. In this case, dress it down with a classic tee and add on some layers like a button-down and bomber. Alternatively, “Add a leather jacket or oversized blazer for a touch of casual edge,” says Michelle.
Sneakers are the perfect finishing touch. There are so many great choices, but right now, we’re especially loving retro-looking sneaks (they go with everything). Another look we love? A fun, colorful sneaker to add a bold pop against a neutral-toned outfit. Think: beige shacket, tonal tee, your favorite jeans and some bright red sneakers. Practical yet super fun—just like your day date.
“Go for a midi skirt with sneakers for an easy yet stylish outfit.” -Michelle, Stylist
Night at the Movies
Ah, the movie date. It’s a classic for a reason. There’s something about a buttery popcorn and crispy soda on a reclining seat that just hits different. Plus, you can always count on the did-you-like-it conversation post credits. Stylist Michelle notes it’s the perfect time to “relax, unwind and look effortlessly put-together,” and we couldn’t agree more. But, what to wear?
It’s all about balance for this stylish date night outfit—something that’s equal parts comfortable and really cute. An undeniable go-to from Stylist Michelle: “Wide-leg jeans paired with a fitted tee and a denim jacket for a touch of layering.”
Another movie date night outfit? Dress things up with a feminine blouse in a fun print. Jeans are still a classic essential, but a trending cuff style or barrel-leg silhouette makes them feel fresh. Finish off with some easy slip-on sandals, suede booties or a clean sneaker. That’s a style wrap.
“Relax, unwind and look effortlessly put-together” -Michelle, Stylist
Ready for Anything
Date night outfits in 2025 can look a little different than usual. For example, if you’re more into that adrenaline rush, you can try axe throwing, escape rooms and hikes…and look good while you’re at it. Stylist Michelle offers the important reminder: “Be ready for anything without sacrificing style.”
Her outfit advice? “Wear stylish yet functional activewear, such as high-waisted leggings and a cropped hoodie.” In the cooler months, pair it with a puffer jacket just in case you feel a chill. You can always tie your hoodie around your waist if needed.
Activewear is the best time to try out a fresh color combo like peach and grey, or navy and cream. We always love a monochrome matching set moment, too. It looks like you put in a ton of effort, even if it only took a few seconds to pull it together.
“Comfortable shoes, like sleek hiking boots or trendy trainers, are a must,” says Stylist Michelle. Nothing like feeling the love by getting your heart pumping.
“Be ready for anything without sacrificing style.” -Michelle, Stylist
Cozy Night In
Dates are truly all about quality time. Sometimes the hustle and bustle of going out is just not the vibe—we get it. Food delivery, good TV and a cuddle sesh is a perfectly acceptable (and romantic) date, too.
Your look can go one of two ways: ultra-comfy cozy or leveled-up lounge. For the former option, Stylist Michelle recommends “Cozy joggers and an oversized sweatshirt for a relaxed look.” And to complete the look: “Slipper booties keep things warm and toasty.” This outfit pairs perfectly with a fireside hot cup of cocoa for two.
Want to level up your chill outfit for date night? Get a comfy-yet-polished look with a plush sweater and a printed jacket. Fair Isle knits are a certified winter classic. Wear it with your favorite pair of perfect-fitting jeans and some lined lug-sole booties. This outfit is ready to run the leaderboard in any game.
“Relax, unwind and look effortlessly put-together” -Michelle, Stylist
Rocking Out
A shared interest of the same music is its very own love language. Stylist Michelle’s outfit for showing up and showing out: “A metallic cami with classic denim and a leather moto jacket and boots for that rocker twist.” If it’s more a jazz band vibe, swap the boots for sleek stilettos for a more polished look. Talk about hitting all the right notes.
More of a casual concert? You can’t go wrong with a vintage-inspired tee (or even band merch). Switch things up with a slip skirt—animal print is current and it adds the perfect amount of edge. Finish things off with a trusty sneaker so you can dance all night long.
“Wear a metallic cami with classic denim and a leather moto jacket for that rocker twist.” -Michelle, Stylist
Get ready for date night with Stitch Fix
Want to look good and feel great on all your dates with the best outfits for any outing, tips and tricks from your very own personal Stylist? Take your style quiz, order a Fix and let your Stylist do the work for you. They’ll choose just-for-you pieces to save you time (and a trip to the mall). Keep what works, and return the rest—or keep 5+ pieces and get 20% off your entire order. Shipping and returns are always free—no subscription required. It’s as easy as 1, 2, 3.
