How to Pick the Perfect Outfit For Every Date

women in date outfits


When it comes to meeting up with a potential crush, or even your spouse, there’s nothing worse than being stressed about what to wear on a date. Whether it’s the first date or the 20th, choosing a date-night outfit can feel daunting. You want a look that’s sure to impress (without upstaging your sparkling personality), feels effortlessly put together (but not overdone), and fits the venue…not to mention the weather forecast. It’s a lot.

Finding the perfect confidence-boosting look shouldn’t be a challenge, and that’s where we come in! Our Stylists have spoken: They’ve pulled some outfits that’ll help seal the deal for another date. Ready? Let’s get serious.

first date outfits for women

What to Wear on a First Date 

You’ve just scheduled a first date with someone you’re excited about (yay, you!). A first meetup is all about getting to know each other, which means it’s time to put your personality—and sense of style—out there.

When plotting your date-night fashion, make sure to keep location, time of day and weather in mind. (Pro tip: If the dress code isn’t immediately obvious, do a little social media sleuthing to see what people typically wear to your venue.)

Now, let’s get dressed: One-and-done styles like dresses and jumpsuits take the guesswork out of curating the perfect ensemble. A versatile slip dress or printed midi silhouette are both easy options to dress up or down. Meeting for a low-key lunch? Throw a chunky cardigan over a floral dress and add minimal white sneakers for an effortless-yet-polished feel. Convening for an after-dark drink? A moody-hued midi, slick leather jacket and ankle boots are sure to impress. 

If dresses aren’t what make you feel your best, leather-look pants are a great canvas for a bold statement top. Go wild with animal prints, sparkling metallics or feather trims, which double as conversation starters.


movie date outfits for women

What to Wear on a Movie Date

Grabbing a bite to eat and catching the latest blockbuster is a classic date-night agenda. When it comes to movie date outfits, it can be tricky to gauge what you should wear. It’s still a date, so you want to look put together…but sitting in a theater (or cuddling up on the couch) for a few hours also calls for a comfy and casual date outfit

Keeping it casual and cool is the move for a cinematic outing. Start by pulling out a few staples that are already hanging in your closet, and let them inspire a date-night worthy look. Your favorite cashmere cardigan is fit for seeing the latest star-studded romcom, especially when paired with a floaty or structured midi skirt. Keep the look feeling effortless with a pair of fresh sneakers, and don’t forget a denim or leather jacket to brave those chilly movie theater temps. If drama is more your genre, novelty denim (think embroidery, embellishments or a colorful wash) will make a statement and keep you comfortable during the two-hour run time. Add a chunky knit sweater or relaxed tee to round out the ensemble, then pass the popcorn. 

hiking date outfits for women

What to Wear on a Hiking Date

Ain’t no mountain high enough! But before you go conquering the great outdoors, first you’ll need to tackle your closet. Whether the activity involves hitting the trails, taking a scenic nature stroll or even rock climbing, active endeavors call for an entirely different dress code than your average evening date. 

For a hiking date outfit, start with lightweight layers (the elements can be unpredictable, after all). Opt for a comfortable base—we like a matching set or breathable technical pants—and an easy tee. Poppy-red leggings are sure to make an impression, while earthy neutrals will look great against any landscape. Add a cool quarter-zip or hoodie, and top it all off with a sporty bomber that looks great on or off the beaten path.

Heading out on a wintry excursion? An insulated puffer coat will keep you feeling cozy and looking chic beyond the trailhead. As for accessories, hands-free is the way to go. A utility-inspired backpack or belt bag is the perfect carryall for snacks, sunnies, water bottles or whatever mother nature requires. And, to help keep you on your feet even as your date sweeps you off them, finish your look with a sneaker-boot hybrid complete with supportive tread.

Dinner date outfits for women

What to Wear on a Dinner Date

Whether you’re invited to a charming little bistro or the most romantic restaurant in town, a dinner date means it’s time to put some effort into your look du jour. When laying out your date-night outfit, the venue should be your first consideration.

Dining at a hip new rooftop spot? A statement top and a pair of feel-great-look-amazing jeans fits the downtown dress code. Opt for a pair with a dark wash and finished hem for a little extra polish, and top it off with your fave going-out top. Delicate lace dials up the drama, while anything puff sleeved and printed is sure to turn heads. Seal the deal with strappy heels or stiletto booties, and don’t forget to grab a standout metallic clutch or shoulder bag on your way out the door. For a meal at an elegant establishment, you can never go wrong with an LBD or JBJ (little black jumpsuit). Whether sheath, a-line or something slinky, be sure to choose a silhouette that highlights your shape and makes you feel your best. Add glistening drop earrings that’ll shine in the candlelight, and you’re ready to rendezvous. 


Get styled by Stitch Fix for date night 

Wondering what to wear for date night? Let our Stylists help get your wardrobe rendezvous ready. Take your style quiz, schedule a Fix and get ready to receive an array of date night outfits that fit your unique taste. Try on your new outfits in the comfort of your own home. Pay for what you love, and send back the rest. Shipping and returns are always free, and there’s no subscription required. You go make a great first impression, and we’ll make sure you feel confident doing it. 

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