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

PDF download Download Article
PDF download Download Article

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

PDF download Download Article
  1. 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. Advertisement
2

Sundress

PDF download Download Article
  1. 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

PDF download Download Article
  1. 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.
    2. Advertisement
4

One-piece swimsuit and short shorts

PDF download Download Article
  1. 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]
    • 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

PDF download Download Article
  1. 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]
    • 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]
    2. Advertisement
6

Athleisure top and pants

PDF download Download Article
  1. 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]
    • 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

PDF download Download Article
  1. 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.
    2. Advertisement
8

T-shirt and jeans

PDF download Download Article
  1. 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]
    • Remember—you don't need to go overkill with your outfit when you're making a first impression! [6]
9

Cardigan and dress

PDF download Download Article
  1. 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]
    • 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.
    2. Advertisement
10

Sweatshirt and joggers

PDF download Download Article
  1. 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

PDF download Download Article
  1. 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.
    2. Advertisement
12

Statement coat, blouse, and pants

PDF download Download Article
  1. 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]
    • Bundle up even more with a cute beanie and mittens.
    • Complete your looks with a pair of tall socks and chunky combat boots.

Join the Discussion...

What do I wear on a first date?
WikiButterflyWhisperer301
WikiButterflyWhisperer301
Going on my first date in a long time and want to look good. What do guys like women to wear? Does anyone have a go-to outift or like rules for a first date? Thanks for the tips!
Stefanie Safran
Dating Coach & Matchmaker
For women, your number one priority should be your comfort! Plan an outfit with shoes that are comfortable. Don't feel like you have to go for a big sexy look. You don't want to feel like you're coming out of your top or your feet are hurting like crazy when you've walked two blocks. Everybody's styles are a little different in terms of what clothes or makeup they like to wear, so you do you! Just make sure not to be overdone with crazy amounts of makeup or jewelry.
Maria Avgitidis
Matchmaker & Dating Expert
If you're meeting someone off of the internet, the best way to make a good first impression is to actually have posted a photo that looks like you and that is recent, because it's not good luck when you don't look like your photo. You should put an accurate photo of yourself on your profile; the person that wants to be with you will want to be with you.

The second way to make a great impression is to actually look the part for the date. So, what I always say is if you're going to go on a date after work, try to do a stop in between the date and the work just to get out of your work mindset: stop at Starbucks for a coffee or a tea, or talk to a friend first. Get out of the work mentality and go into your date mentality. Those are totally different people, especially for most women.

Look the part, hopefully put an effort into the impression you want to give to this person. That means wearing either well-fitted jeans or a nice dress, nice shoes, heels or flats. Look like you're taken care of, make sure your hair looks good, and overall you're comfortable. A first date is not the place to wear something you just bought that you're not comfortable in yet. The first date is a time to wear something that you definitely feel comfortable in, that makes you feel good and makes you look good.
See all 13 Replies and
Read Discussion

Expert Q&A

Search
Add New Question
  • 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.
    Thanks! We're glad this was helpful.
    Thank you for your feedback.
    If wikiHow has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission. Support wikiHow
    Yes No
    Not Helpful 0 Helpful 1
  • 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.
    Thanks! We're glad this was helpful.
    Thank you for your feedback.
    If wikiHow has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission. Support wikiHow
    Yes No
    Not Helpful 1 Helpful 3
Ask a Question
200 characters left
Include your email address to get a message when this question is answered.
Submit
      Advertisement

      Tips

      Submit a Tip
      All tip submissions are carefully reviewed before being published
      Name
      Please provide your name and last initial
      Submit
      Thanks for submitting a tip for review!

      You Might Also Like

      170+ Deep, Heartfelt & Passionate Love Messages to Send Your Guy
      How to
      Make Your Girlfriend Want to Have Sex With You
      45 Sweet Paragraphs That’ll Make Your Girlfriend Cry
      How to
      Turn a Girl On
      150+ Romantic & Funny Questions to Make Your Boyfriend Laugh
      How to
      Prepare for Your First Time for Guys
      How to
      Tell if Your Boyfriend Is Gay
      28 Funny Jokes to Tell Your Girlfriend
      How to
      Kiss Your Boyfriend to Make Him Crazy
      How to
      Turn On Your Girlfriend
      How to
      Find Out if a Guy Secretly Likes You
      How to
      Tell if Someone Has a Dating Profile
      50+ Conversation, Board, and Video Games to Play with Your Girlfriend
      Signs a Woman is Sexually Attracted to You
      Advertisement

      References

      1. ↑ https://www.collegefashion.net/fashion-tips/what-do-i-wear-there-amusement-parks/
      2. ↑ https://youtu.be/uRm5qYXOoek?t=421
      3. ↑ Lisa Shield. Dating Coach. Expert Interview. 13 December 2018.
      4. ↑ https://www.gq-magazine.co.uk/article/what-to-wear-on-a-first-date
      5. ↑ Lisa Shield. Dating Coach. Expert Interview. 13 December 2018.
      6. ↑ Lisa Shield. Dating Coach. Expert Interview. 13 December 2018.
      7. ↑ https://youtu.be/dkysewH0QiU?t=431
      8. ↑ https://www.glamour.com/gallery/winter-date-outfit-ideas

      About This Article

      Thanks to all authors for creating a page that has been read 24,039 times.

      Did this article help you?

      Advertisement