3 Cute Outfits To Wear With Slip-On Sneakers

At one time the only ones wearing slip-on sneakers were suntanned teenage skateboarders in California!  But no more. Slip-on sneakers have gone mainstream and are a favorite of young and old. Women of every age are huge fans of these hip-comfort shoes. In fact, they’ve even been spotted in the streets of Paris!

Thousands of patterns, colors, and styles make slip-on sneakers fun and exciting to wear with your favorite casual outfit.  If you are wondering how to style them, here are 3  cute ideas for what to wear with slip-on sneakers this spring and summer!

white Slip on sneakers and jeans

1.  Wear Slip-On Sneaker With Cropped Pants 

Wearing sneakers with a t-shirt and cropped jeans is a super casual no-brainer but there’s just something about a slip-on sneaker that takes the overall look up a notch. Make that two when you wear a slip-on sneaker with a little personality like these star-embellished ones from Michael Kors.

Not only would they make simple jeans and t-shirt outfits a little dressier, but they also hold their own in a more polished version of that classic uniform like the one I show here. With a chic bag and the t-shirt swapped out for a more formal shirt or blouse, regular sneakers would look clunky and not quite right. But these slip-on’s are perfect.

raffia slip on sneakers with shorts

2.  With Shorts

Many women balk at the thought of wearing shorts after 40 but hey, why not on a hot summer weekend? The trick is to find a pair that works with your body and that isn’t too long or too tight. (For more tips on how to wear shorts after 40, check out my post here.) Slip-on sneakers make shorts look hip and cool. They’re more sophisticated for an over-40 gal than regular running shoes and a starting point to build a cute summer outfit around. These raffia wedge sneakers are summery and fun.

Your choice of tops is important too. The goal is to look classy, not trashy, so when you’re showing some skin on the bottom half like you do when you wear shorts, keep things a little more covered up on the top. A never-fail recipe is to wear a pair of shorts with a classic white button-down.


3.  Yes, Slip-On Sneakers Can Be Worn With A Dress

You wouldn’t think to wear sneakers with a dress, but they actually look really cute with a casual sporty style. This cute cotton t-shirt dress with its relaxed vacation vibe is the perfect match for these sunny, gold slip-on sneakers in suede that are sure to bring a smile to everyone’s face.

Tuck these away in your suitcase when you go on holiday this summer. They’re comfy, easy, and easy to kick off when you want to put up your feet and have yourself a margarita!

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5 thoughts on “3 Cute Outfits To Wear With Slip-On Sneakers

  1. I enjoy reading all your fashion articles; you are spot on! I am 50-plus years old and fond of leggings.
    I just wanted to inquire about wearing leggings with flats or ballet flats shoes. Is it okay if there is a skin gap between the tapered end part of the legging and the heel of the foot? Or should we cover the whole heel with the legging? I.e., that means very long leggings. I notice my leggings tend to shrink a little after use, so revealing that gap of skin.
    Kindly advise, please.

    1. Hi MB,
      Thanks for dropping by. It’s lovely if your leggings end above the ankle, at the ankle, or just below the ankle. You don’t need to cover your heel with your legging at all. I think it looks most chic just at the top of the ankle. Please have a look at these posts to see how they are worn. Cheers, Deborah or or

  2. Not a big fan of slip-on sneakers. I think they look clunky on me so I will stick to a cute pair of sandals for spring & shorts weather…

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