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What to Wear on a Casual First Date

Updated: May 2

by Siobhan Quinn

Photo by Helena Lopes from Pexels

The spring season is beginning to bloom and love is in the air—and you have a casual date to plan for! What better way to spend an afternoon than strolling with someone you fancy, listening to the birds chirping, and feeling the sunshine on your skin? Going for a walk with your date is an amazing way to build a connection, get some fresh air, get your body moving, and take in the beauty of the world around you. Deciding to plan a walking date is the easy part. What’s more difficult, however, is figuring out what to wear. You want to be comfortable, but cute. Stylish, but functional. Well, babe, you can do it all with these simple tips.


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Layers are your Best Friend!

Unless the weather forecast shows very hot temperatures, layering up may be in your best interest. Even if it’s 65 degrees outside, you never know how that temperature may fluctuate once you’re actually out in the open. A strong breeze could leave you shivering and unable to focus on anything else besides how chilly it is, effectively lowering the quality of your date. Instead, come prepared with a layer or two—a cardigan over your tee shirt, a flannel over your tank top, a denim jacket over your sleeveless dress. Should you find yourself too warm at any point, you can just take the top layer off and tie it around your waist for an effortlessly cute look. And if you guys are walking in the shade and you’re beginning to shiver, you can throw it back on. Simple, easy, cute.


Wear Clothes that Give You a Good Range of Motion.

How loose or tight you want your clothing to be is entirely up to you. But when it comes to a walking date, you don’t want to wear anything too rigid that lacks proper breathing room. Your new leather pants may be cute AF, but how comfortable would you be walking for an hour in them? That v-neck crop top is gorgeous, but will you be constantly worried about a rogue boob popping out? Choose stretchy clothes that are easy to move around in, and make you feel confident. This could be a babydoll dress or biker shorts with a light crewneck sweater. Whatever comfortable clothes you choose, make sure they reflect you!

The Shoes You Choose Matter!

If you take nothing else from this article, take at least this piece of advice: Wear comfortable shoes! There’s nothing worse than having to cut your date short because your feet are hurting or you’re getting a bad blister. Wear a pair of shoes that you know for sure you don’t have any issues walking in. If it’s a new pair of shoes, wear them around the house or while running errands to make sure they don’t start bothering you after extended use and lots of walking. But this doesn’t mean your shoes can’t be cute! Although those high heels and wedge sandals might not be the right fit for this date, there’s a time and a place for them down the road. For now, consider wearing something like Allbird's Wool Pipers or these cute sandals from Skechers. Your feet will thank you!


The next time you’re preparing for a casual date, remember: You don’t have to sacrifice comfort for fashion or vice versa. You can wear clothes that make you feel good and look even better—ones that don’t leave you too cold, too hot, or in pain. Stay safe, stay cute, and stay comfortable out there, loves!