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October 18, 2024

What To Wear on a Date: 15 Stylish Outfit Ideas

Source: iStock.com/ArthurHidden

There's nothing quite like the mix of excitement and nerves before a first date. And while you might wonder what you'll talk about and whether you’ll make a good impression, the most stressful pre-date worry is landing on the perfect outfit.

To help you decide what to wear on a date, we've done some thorough outfit research. Read on for get-ups that will have you looking and feeling your best, no matter the activity.

What you should wear on a first date: 15 ideas

The key to dressing for a first date is matching your look to the atmosphere. Whether you're going for casual coffee, a laid-back picnic, or a romantic dinner, your clothes should reflect your personal style and the outing’s setting. 

We've compiled a list of 15 outfit ideas for first dates to help you feel confident and make a great impression.

Walk-and-talk date

A low-key strolling date calls for a casual but stylish outfit. You want to feel comfortable and look great without going overboard. These options will help you strike the perfect balance.

1. Jeans, shirt, and sneakers 

Woman in blue jeans, matching denim jacket, white tee, white sneakers, cream cap, and a cream handbag on her shoulder.
Source: Image generated by ThredUp’s AI-powered Style Chat

It doesn’t get much more laid-back than this. Complement your favorite pair of jeans with a simple shirt for a breezy walk in the park. Add a pair of classic white sneakers and complete the look with a light jacket that suits the weather.

2. Maxi dress, denim jacket, and flats

Woman in a floral maxi dress, wearing a denim jacket on her shoulder, white sneakers, and posing with her right arm elevated behind her head.
Source: Fab_1/Shutterstock

When you're feeling a bit more flirty, reach for a flowy maxi dress. Wear it with a cropped denim jacket and flats for a relaxed vibe. If you'll be doing lots of walking, you can also swap the flats for a pair of sneakers. This outfit is perfect for a stroll around the city or a wander through the farmers’ market. 

3. Leather jacket, T-shirt, and jeans

Woman in black skinny jeans, white tee, black leather jacket, black ankle boots, and sunglasses, holding a black handbag with silver details.
Source: Image generated by ThredUp’s AI-powered Style Chat

Add a bit more edge to a casual first date with leather. Layer a fitted leather jacket over a white T-shirt and wear your favorite jeans to complete the look. Black loafers or ankle boots keep the outfit classy yet comfortable. 

Coffee date

A coffee date at a cute cafe feels slightly more romantic than a walk in the park. That said, we still recommend wearing comfortable shoes in case you extend the date with an impromptu stroll. Here are a few outfit ideas.

4. Striped blouse, cropped jeans, and ballet flats

Woman wearing a striped white and gray blouse, blue cropped jeans, round white-framed sunglasses, black ballet flats, and a white handbag with a light scarf tied to its brown handle.
Source: Image generated by ThredUp’s AI-powered Style Chat

Tuck a light, breezy striped blouse into cropped jeans for a put-together look. This outfit is simple to assemble and looks especially great with ballet flats. Add a colorful crossbody or bucket bag for a functional but playful touch.

5. Turtleneck, mini skirt, and sneakers

Woman in a black leather mini skirt, dark green turtleneck, light gray scarf, black knee-high boots, sunglasses, and holding a handbag with a golden chain.
Source: Image generated by ThredUp’s AI-powered Style Chat

If you want to look smart and approachable, a fitted turtleneck with a mini skirt is always a great idea. Pair the outfit with clean, minimalist sneakers to keep things comfortable. You can also wear this look with knee-high boots for an edgier take. Since turtlenecks are quite warm, this is an ideal choice for a fall outing.

6. Oversized sweater, boyfriend jeans, and ankle boots

Woman wearing a gray oversized knit sweater, white scarf, blue boyfriend jeans, round sunglasses, black ankle boots, and a black handbag on her shoulder.
Source: Image generated by ThredUp’s AI-powered Style Chat

Grab a macchiato with your latest crush in an oversized sweater and relaxed-fit boyfriend jeans. This ensemble is just elevated enough with chic ankle boots. When your date goes longer than intended, the outfit transitions perfectly for dinner out or an evening on the couch. 

Movie date

If you're wondering what to wear for a first date at the movies, think comfortable but still classy. The following outfits offer enough wiggle room for you to be able to sit back and enjoy the show.

7. Cropped hoodie, high-waisted jeans, and sneakers

Woman wearing a black cropped hoodie, high-waisted jeans, dark blue coat, white sneakers, round sunglasses, and holding a yellow leather tote.
Source: Image generated by ThredUp’s AI-powered Style Chat

You can't go wrong with a cropped hoodie and high-waisted jeans. Add your go-to sneakers and a mini backpack or small tote bag, and you have the perfect outfit for a casual movie date. Movie theaters can get chilly, so bring a jacket or coat if you want a layer. 

8. T-shirt dress, bomber jacket, and slip-on sneakers

Woman in a graphic T-shirt dress, black bomber jacket, boots, sunglasses, and a dark red shoulder handbag.
Source: Image generated by ThredUp’s AI-powered Style Chat

Wear a T-shirt dress with a bomber jacket and sneakers for a weekend movie date. This slightly dressier theater look is great for evening showtimes without being too done up. If you're worried about getting cold, swap the sneakers for boots and add a thick pair of tights. 

9. Leggings, chunky knit sweater, and knee-high boots

Woman wearing black leggings, a cream chunky knit sweater, a scarf, and black ankle boots, holding a black handbag.
Source: Image generated by ThredUp’s AI-powered Style Chat

Want to look polished without sacrificing comfort? Pair a chunky knit sweater with your favorite black leggings. Add ankle boots, and you've got a fashionable movie date outfit that's ultra cozy. 

Dinner date

Going out to restaurants calls for a more sophisticated look than other casual activities might, so it’s a fun opportunity to show off your upscale style. Here are three outfit ideas sure to impress.

10. Little black dress, strappy heels, and clutch

Woman wearing a black dress, black strappy heels, a belt, and sunglasses, holding a black clutch purse with turquoise details.
Source: Image generated by ThredUp’s AI-powered Style Chat

A little black dress is a classic option for a dressy first date at an upscale restaurant. Pair it with strappy heels, bold earrings, and an embellished clutch for an elegant look. If black isn't your thing, try a party dress in a fun color with more understated accessories. 

Pro tip: Buy your dress online on ThredUp for a fraction of the retail price. 

11. Blouse, pleated midi skirt, and pumps

Woman wearing a pale purple pleated midi skirt, pale pink heels, a white flowy blouse, and sunglasses, holding a pale pink handbag.
Source: Image generated by ThredUp’s AI-powered Style Chat

If you love a dreamy rom-com look, a pleated midi skirt with a flowy blouse is an excellent choice. This feminine outfit is elegant and can be worn with pumps or flats. For cooler evenings, add a fitted blazer

12. Silk top, tailored trousers, and heeled sandals

Woman in a dark green silk top, tailored black trousers, heeled sandals, and sunglasses, holding a light brown handbag, with a small medallion around her neck.
Source: Image generated by ThredUp’s AI-powered Style Chat

For a more casual dinner, try a silk top and sharp trousers. Add strappy sandals if it's warm out or heels if you want some lift. A structured purse takes this outfit to the next level. 

Outdoor adventure date

If your first date involves an outdoorsy activity like hiking or rock climbing, you need a practical outfit that looks great and lets you move. Get inspired from one of these ideas.

13. Athleisure set, lightweight jacket, and sneakers

Woman in a matching dark blue athleisure set, white sneakers, and an orange lightweight jacket, wearing large sunglasses and holding a black backpack.
Source: Image generated by ThredUp’s AI-powered Style Chat

A matching athleisure set is trendy and high-performance. Add a lightweight windbreaker or denim jacket to keep you warm, and don't forget to pack a sporty backpack with necessities like snacks and water. Complete the look with a pair of functional sneakers. 

14. Leggings, oversized sweater, and hiking boots

Woman in black leggings, a dark red knit sweater, and a knit beanie, wearing black hiking boots and resting her hand on the straps of a backpack.
Source: Image generated by ThredUp’s AI-powered Style Chat

Athletic leggings with an oversized sweater is the perfect cool-weather hiking outfit. This look is laid-back without being sloppy and lets you move freely to keep up with your date. Complete the outfit with sturdy hiking boots that provide support for whatever the day has in store.

15. Shorts, flannel, and sandals

Woman in denim shorts, a cream tank top, and an open dark green and blue flannel shirt, wearing brown sandals and sunglasses, with a dark red belt bag on her waist.
Source: Image generated by ThredUp’s AI-powered Style Chat

Wear shorts and a tank top if you're headed to a sunny outdoor spot. Add a flannel in case there's a breeze and choose thick sandals made for walking. You can store your keys and phone in a belt bag to keep your hands free while you adventure.

Find your first-date clothes on ThredUp

Choosing the perfect outfit helps you put your best foot forward on a first date. Whether going for a casual coffee or a fancy dinner, dressing to suit the occasion is just one way to look and feel confident.

If you have a date coming up, ThredUp takes the stress out of finding the ideal look. Our platform lets users buy and sell clothes online, with an extensive collection of preloved garments from top brands. Find specific items with our Improved Search feature or use our Style Chat feature for style inspiration. We drop over 5,000 new items daily at up to 90% off typical retail prices.

Explore ThredUp today to build a wardrobe that's sustainable, affordable, and first-date ready.