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You’re going on a first date — eek! You’ve been counting down the days...but now you have to find something to wear. Ugh. It can be tricky picking out a first date outfit when there are so many factors to consider. Is it a casual date? A fancy dinner, an outdoor lunch, or a chill coffee date? Will the movie theater be cold, or should I just wait for my date to offer their jacket? Or even the worst-case scenario: the perfect outfit you picked out days ago is suddenly stained, see-through, or ripped?!
It happens to the best of us. Here’s some good news, though: great first date outfits won't require you to change yourself, your style, or the things you love to wear based on what you think they’ll like (that’s a recipe for feeling uncomfortable all night). But you do want to be strategic based on the occasion. Are you going mini golfing on a windy pier? Jeans will be way more comfortable than a mini skirt that keeps blowing up. Matching bike shorts and a crop top set are perfect for a hiking date, but not so much if you’re splashing out on a fancy dinner.
Common Mistakes to Avoid:
- Wearing brand new shoes, especially if you’re walking a lot. Blisters will make you uncomfortable even on the best first date ever.
- Not keeping the weather in mind — bring a denim jacket if you’re headed to the movies (they love blasting the AC!) or wear layers you can take off if you’re eating outside and end up sitting directly in the sun.
- Wearing clothes that you don’t feel 100% comfortable in — you’ll spend the evening tugging down the hemlines and adjusting your straps rather than getting to know your date.
Most importantly, remember that a first date isn't a test, it's a chance for you to get to know the person you’re with. If it works out — amazing. If it doesn’t, you now have a super cute outfit ready to be re-worn on your next date. Get ready to feel your best in these time-tested first-date outfit ideas.
Casual Date Vibes
A denim mini skirt is the perfect balance of chill and cute in an I-didn't-really-try kind of way, if that's what you're going for. Pair it with a simple tank and your favorite leather jacket for a polished, laid-back vibe.
REMI x REVOLVE Chloe Faux Leather Blazer in Black
EDIKTED Chiara Low Rise Denim Miniskirt
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First Date Denim
“Can I wear jeans on a first date?” YES. Absolutely, you can. They aren't too casual, if you were worried about that. A cute corset or tube top will balance out your chill jeans.
ALICE + OLIVIA Cristi Cropped Crepe-Paneled Tweed Top
ALICE + OLIVIA Cristi Cropped Crepe-Paneled Tweed Top
Now 55% Off
RE/DONE Comfort Stretch Ultra High Rise Wide Leg
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Romantic Date Energy
Enter your Bridgerton era with a puff-sleeved dress with a Soft Girl floral print. Oh, and a pro tip for a date outfit? Printed fabrics are wayyyy more forgiving when it comes to hiding stains. Phew!
Linsery Puff Sleeve Floral Print Ruched Dress
Linsery Puff Sleeve Floral Print Ruched Dress
Active & Outdoors
If your first date is an outdoors-y activity (think hiking a trail, going on a scavenger hunt, riding bikes, etc) bike shorts are the perfect cute-but-practical option. Pair them with your comfiest graphic tee and sunnies, and you’re ready.
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Smart Shoe Options
Block heels and heeled boots are always a better option than stick-thin stilettos, even if you aren’t planning on doing a lot of walking on your first date. What if you end up extending your date and taking a stroll while talking all night? Thicker heels are easier on your feet — trust.
Wenrine Crew Neck Ribbed Bodycon Dress
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Spring Has Sprung
If you’re just grabbing ice cream or going for a walk outside on the first date, go with a more casual sundress that still looks put together. Stack a couple of necklaces and try a fun hairdo like a bubble ponytail or french braids with butterfly clips.
AE x The Summer I Turned Pretty Knit Cami Mini Dress
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Year-Round Knit Dresses
A knit collared dress gives sporty-chic energy, especially if you accessorize with a cool pair of sneakers. It’s comfortable, AND it can be dressed up with statement earrings and a mini purse if you need it to feel fancier.
Little Black Dress >>
The sweetheart neckline looks romantic on everyone, and any other details like little bows or ruffles are too cute for words. Need a formula that always works? LBD + colorful heels and earrings.
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Comfort First
The last thing you want to be worrying about on a first date is if your shirt is riding up or not staying in place. Looking for a solution? One word — bodysuits.
Hannah Oh
Assistant Shopping Editor
Hannah is the assistant shopping editor at Cosmopolitan, covering all things from cute apartment decor to trendy fashion finds, TikTok products that are actually worth your $$$, and the perfect gift to buy for your boyfriend's mom. She previously wrote for Seventeen and CR Fashion Book. Follow her on Instagram for hot takes on red carpet fashion and unhinged updates on the books she’s reading on the train.
