12 First Date Outfits That’ll Make You Feel Comfy and Confident (2024)

12 First Date Outfits That’ll Make You Feel Comfy and Confident (1)

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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

12 First Date Outfits That’ll Make You Feel Comfy and Confident (2)

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

12 First Date Outfits That’ll Make You Feel Comfy and Confident (3)

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EDIKTED Chiara Low Rise Denim Miniskirt

12 First Date Outfits That’ll Make You Feel Comfy and Confident (4)

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First Date Denim

12 First Date Outfits That’ll Make You Feel Comfy and Confident (5)

“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.

RE/DONE Comfort Stretch Ultra High Rise Wide Leg

12 First Date Outfits That’ll Make You Feel Comfy and Confident (7)

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Romantic Date Energy

12 First Date Outfits That’ll Make You Feel Comfy and Confident (8)

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

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Active & Outdoors

12 First Date Outfits That’ll Make You Feel Comfy and Confident (10)

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

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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

12 First Date Outfits That’ll Make You Feel Comfy and Confident (13)

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Vince Camuto Membidi Bootie

12 First Date Outfits That’ll Make You Feel Comfy and Confident (14)

Spring Has Sprung

12 First Date Outfits That’ll Make You Feel Comfy and Confident (15)

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

12 First Date Outfits That’ll Make You Feel Comfy and Confident (16)

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Year-Round Knit Dresses

12 First Date Outfits That’ll Make You Feel Comfy and Confident (17)

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.

Madewell Ribbed Polo Knit Mini Dress

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Little Black Dress >>

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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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SNDYS Barcelona Dress

12 First Date Outfits That’ll Make You Feel Comfy and Confident (20)

Comfort First

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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.

12 First Date Outfits That’ll Make You Feel Comfy and Confident (22)

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.

12 First Date Outfits That’ll Make You Feel Comfy and Confident (2024)

FAQs

What should a 13 year old wear on a first date? ›

For an active date, consider nice shorts, capris, or pants; a skirt or dress may make it more difficult for you to move around in. Pair your bottoms with a fun top; an off-the-shoulder blouse or a patterned tank top would work well. For a date at the movies, a restaurant, etc. you could choose a skirt or dress.

What is the perfect date outfit? ›

You want your outfit to feel as laid-back as the date. "Opt for a casual, easy vibe," Priyanka says. "Keeping it low-key is the main focus." As jeans are practically the definition of casual, they're an ideal choice. "Light-wash, high-waist denim with a T-shirt is a great look and also very classic," Priyanka notes.

How do I look impressive on a first date? ›

First Date Tips: How to Impress and Score a Second Date
  1. Dress Comfortably. ...
  2. Plan an Activity. ...
  3. Ask Questions. ...
  4. Big Talk Beats Small Talk. ...
  5. Resist Drinking Too Much. ...
  6. Talk About the Future. ...
  7. Extend the Date. ...
  8. Pay Attention to Body Language.
Apr 10, 2019

How do I look confident on a first date? ›

Stand/sit tall with your shoulders back and head held high, walk with intention, smile, make eye contact and voila; you're looking more confident in an instant. What you wear will also affect your visual impact — we'll delve into that shortly.

What colors do guys find most attractive? ›

Scientists have revealed that wearing the colour red will make you more attractive to the opposite sex. Studies reveal that red is the most attractive colour to both men and women but, curiously, the two genders are attracted to the same colour for different reasons.

What do guys want a girl to wear on the first date? ›

The bottom line is that there is no specific item men want to see a woman wear—on dates or otherwise. One friend mentioned that a girl's style should just be "proper for the occasion." If we're going out for fancy drinks or dinner, a co*cktail dress is always nice to see. Jeans are great for dive bars and movies.

Should you wear your hair up on a first date? ›

If you want to keep the focus on your clothing, like you're a model or walking a red carpet, then go updo. If you want your face and outfit to flow together for a first date or casual days, then let your locks hang low.

Is it OK to have a BF at 13? ›

Healthy friendships are encouraged for teenagers between 13 and 15, but romantic relationships could be too much for them to handle. Parents should discuss dating guidelines with their teens and monitor their behavior closely while providing support and guidance as needed.

Is it OK to date at 13 or 14? ›

Rest assured that it's totally normal for a 14-year-old to be interested in dating, and this is a healthy, important part of growing up. However, that doesn't mean that their relationship will look a whole lot like a regular adult relationship.

Will a relationship at 13 last? ›

High school relationships can last, but they're not always common. According to CDC study, relationships starting at a younger age have higher breakup rates, but some high school sweethearts stay together long-term. The maturity level and goals of the individuals often help determine the relationship's success.

What bra to wear on a date? ›

Rock the off-shoulder top with a pair of jeans or a skirt and your date is yours. Wondering what bra to wear with it? Go for a strapless bra and stay care-free. Your eyes should be on him and not on your bra straps.

How can I look attractive on a date? ›

17 Great Dating Tips to Make You Instantly More Attractive
  1. Have a ready-made smile to appear fun and happy. ...
  2. Don't be negative - no one likes a Debbie Downer. ...
  3. Playing hard to get will make you more desirable. ...
  4. Try and relax in order to really connect with a date. ...
  5. Exercise to wow your date both physically and mentally.
Jan 5, 2024

What a girl looks for on a first date? ›

One of the most important things that women want on a first date is to feel comfortable. This means that the man should make an effort to put her at ease and make her feel comfortable in his company. The man should also be a good listener and be interested in what she has to say.

Is it standard to kiss on the first date? ›

There's no one right answer to this question. In some circ*mstances, it might be appropriate to kiss on the first date, but it can depend on a variety of factors. For example, it can be important to consider how your date feels about it and whether you feel comfortable kissing someone that you're just getting to know.

How can I be attractive on a first date? ›

17 Great Dating Tips to Make You Instantly More Attractive
  1. Have a ready-made smile to appear fun and happy. ...
  2. Don't be negative - no one likes a Debbie Downer. ...
  3. Playing hard to get will make you more desirable. ...
  4. Try and relax in order to really connect with a date. ...
  5. Exercise to wow your date both physically and mentally.
Jan 5, 2024

What is acceptable on a first date? ›

When you're planning a first date, don't go somewhere too fancy or too loud. Pick somewhere lighthearted and relaxed. You want to hear and experience the other person. The point of a first date is to see how well you connect with each other—not how much you spend on dinner or how good you read lips over drum solos.

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