What to Wear on a Walking Date: 11 Stylish Outfit Ideas

Co-authored by Lisa Shield and Hunter Rising

Last Updated: April 20, 2022 References

If you're heading out for a walking date, how can you dress to impress while staying comfortable? Even if you have a lot of outfits to choose from, striking the balance between stylish and practical clothes is as easy as a walk in the park. Keep reading for a list of complete outfit ideas, from the hottest summer styles to the best looks for when the weather cools down!

1

Crop top and dark denim

A statement crop top will be attractive and eye-catching. Crop tops are perfect if you want to stay cool and show off a bit of your tummy, so pick a flirty top that shows some skin. Stick to bright colors or interesting patterns since they’ll look like you’re dressing up more for the date. Finish your outfit with a classic pair of dark jeans or short shorts.
- Stick with flats or a pair of strappy sandals to tie your whole look together.

2

Sundress

A patterned dress looks great when you’re out in the summer sun. Sundresses come in so many different lengths and colors, so try a few on to see what looks best on you. Keep in mind where you’re going for a walk so you don’t wear anything that could drag on the ground or easily snag.
- Wear a floppy hat or a pair of sunglasses to keep the sun out of your eyes.
- A pair of flat sandals, sneakers, or espadrilles are great options to help you stay comfortable.

3

Tank top and skirt

Beat the heat of a hot summer day with this cute fit. Pick a solid-colored tank for a clean and simple look, or choose one with a fun pattern if you want to make your outfit stand out. Stick with a mini or midi skirt so it’s easier to walk around without getting caught in the fabric. You can either leave your tank untucked for a casual look or tuck it into your skirt if you want to look a little more put together.
- Accessorize with a chunky necklace to draw your date’s eye to you.
- If you’re worried about the temperature dropping, bring a jacket or sweatshirt with you. You can always tie it around your waist if it’s too warm.

4

One-piece swimsuit and short shorts

Try this versatile outfit for a romantic stroll on the beach. A one-piece swimsuit can be a great alternative to a regular tank top if you’re spending your date near the water. Put your favorite pair of shorts over your swimsuit to finish your look. You can easily pop into the water for a dip if the moment feels right.^{[1]
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- Bring along a light sweatshirt or jacket in case it gets a little chilly.
- Complete your outfit with a comfortable pair of chunky sandals or slides.

5

Statement blouse and shorts

A bright or patterned blouse is sure to catch your date’s eye. Pick a top that has a busy pattern or bright color since it will make your date look over at you more. On a warmer day, choose a sleeveless or short-sleeved top. If you’re afraid of getting cold, stick with long sleeves that you can roll up. Tuck your top into a nice, clean pair of denim or khaki shorts that show off your legs.^{[2]
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- Tennis shoes are a great choice to stay comfortable while you’re walking, but a pair of flats or sandals work well too.
- Pair your blouse with a nice pair of jeans and some boots for a sexy, classic outfit.^{[3]
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  Expert Source
  
  Lisa Shield
  Dating Coach
  Expert Interview. 13 December 2018.}

6

Athleisure top and pants

This athletic style fits tight and shows off your body. Since you’re staying active during your date, it makes sense to wear an outfit you’d normally work out in. Any tight, breathable fabric works well, so try out options like a sports bra with a crop-top hoodie, a tank top, an athletic tee, a cute windbreaker, leggings, or yoga pants to look stylish on your date.^{[4]
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- Since athleisure clothes don’t have a lot of pockets, bring along a small purse or a fanny pack to hold the rest of your things.
- Rock a pair of matching sneakers or trainers with your outfit to finish off your look.

7

Athletic shirt and shorts

You’ll stay cool and comfortable if you’re hitting the hiking trails. A more strenuous hike could make you sweat more, so dress in breathable moisture-wicking athletic clothes. Try out a cute form-fitting shirt or tank top with a light sweatshirt or jacket layered over it in case you get cold. Any breathable pair of shorts or athletic leggings look great and complete your outfit.
- For summer hikes, make sure you bring a hat and some sunscreen.
- If you’re going on a difficult trail, wear hiking boots so you have more traction. For a flat, easy trail, sneakers are a great pick.
- Avoid wearing cotton clothes since they take a long time to dry if they get sweaty.

8

T-shirt and jeans

Rock this classic, comfortable style no matter when you’re going out. Stick with solid-colored or simple patterned shirts rather than graphic tees so you look a little more dressed up. Rock a pair of jeans that fit tight on your legs, but not so tight that you have a hard time moving around.
- Try wearing a red shirt since the color can make you look more attractive.
- Accessorize with some jewelry, like bracelets or a belt.
- Put on a pair of sneakers to finish your outfit.
- Layer a leather jacket on top for a really cool, classic look.^{[5]
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  Expert Source
  
  Lisa Shield
  Dating Coach
  Expert Interview. 13 December 2018.}
- Remember—you don't need to go overkill with your outfit when you're making a first impression!^{[6]
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  Expert Source
  
  Lisa Shield
  Dating Coach
  Expert Interview. 13 December 2018.}

9

Cardigan and dress

This cute layered combo looks amazing on a chilly night. Stick with midi dresses so you can easily walk around without dragging or snagging any of the fabric. Choose a cardigan that has a neutral color or is complementary to your dress so it doesn’t clash. That way, you have the option to button up when you start feeling cold.^{[7]
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- If you’re still feeling cold, put on a pair of tights or leggings underneath your dress.
- Chunky sneakers or combat boots can complete your look.

10

Sweatshirt and joggers

Go for this relaxed, athletic look when it starts to get colder outside. Choose a fitted sweatshirt that hugs your body since it will look a little nicer than if it were baggy. Rather than wearing a loose pair of sweatpants, stick with joggers since they’re a little tighter on your leg and will accentuate your body. If you want to coordinate your whole outfit and look put together for your date, try out a matching tracksuit.
- Put on a pair of tennis shoes or trainers with your outfit so you’re ready to walk around.

11

Sweater and leggings

You’ll feel chic and comfortable in this autumn and early winter fit. This style looks great when it starts getting chilly, but might be a little too cold for later in the season. An oversized knit sweater works great since you can wear it like normal or slide it off of your shoulder for an even flirtier look. Finish your outfit with a pair of insulated leggings so you don’t get chilly.
- Wrap a scarf around your neck for an even more bundled look.
- A pair of knee-high socks and tall boots can help keep your legs from getting colder.

12

Statement coat, blouse, and pants

Stay warm and stylish with this multilayered look. If you’re out walking on a winter date, plan ahead by putting on a coat that makes you stand out. Make sure you still dress up with your favorite blouse and a comfortable pair of pants underneath so you still look great if you need to take your coat off.^{[8]
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- Bundle up even more with a cute beanie and mittens.
- Complete your looks with a pair of tall socks and chunky combat boots.

Expert Q&A

Question

What should a guy wear on a first date?

Lisa Shield
Dating Coach
Lisa Shield is a love and relationship expert based in Los Angeles. She has a Master's degree in Spiritual Psychology and is a certified life and relationship coach with over 17 years of experience. Lisa has been featured in The Huffington Post, Buzzfeed, LA Times, and Cosmopolitan.

Lisa Shield

Dating Coach

Expert Answer

Wear something clean that wasn't just pulled out of the laundry pile. A nice pair of jeans and a T-shirt can work well for a first date—you don't need a tie or anything.
Question

How can I be sexy for a date?

Lisa Shield
Dating Coach
Lisa Shield is a love and relationship expert based in Los Angeles. She has a Master's degree in Spiritual Psychology and is a certified life and relationship coach with over 17 years of experience. Lisa has been featured in The Huffington Post, Buzzfeed, LA Times, and Cosmopolitan.

Lisa Shield

Dating Coach

Expert Answer

Wear a balanced outfit! For example, you could pair a lower-cut blouse with a nice pair of jeans, or wear a long-sleeve shirt with a short skirt.