10 Shoes to Wear With Shorts

Summer is here, and shorts are a favorite of mine for the season! It’s the perfect time to break out those shorts and enjoy the warm days. I personally love wearing them because they keep me cool and comfortable, making them perfect for any summer occasion. I also love how switching up my shoes and shorts pairings gives me an endless list of outfits to wear. So, today, I’m sharing a round up of 10 shoes that go well with shorts. From classic sneakers to sandals and more, these shoe options will help in making styling your shorts outfits easy and fun!

Also, if you’re looking for shoes to style with your dresses this summer, be sure to check out my 6 Shoes to Wear With Summer Dresses post to get inspired.

10 Shoes to Wear With Shorts

what Shoes to Wear With Shorts

Sharing a variety of chic shoes to style with your shorts this season.

Classic Sneakers

Classic sneakers are a go to option of mine for pairing with shorts. They are perfect for when you want to feel comfortable, but still look cute. Making them great for casual outings like picking up the kids from school, a casual day out, travel days, and more. I also really like opting for a jean shorts outfit paired with chic sneakers, like Adidas Sambas. Then, pairing that with a simple tee for a relaxed, everyday look. My agolde jean shorts are definitely my go to when reaching for a comfortable and stylish pair.

Ballet Flats

Ballet flats are always a great option when you want a chic and polished look with shorts. When I want to look sophisticated while wearing shorts, I opt for black shorts outfits. Also ballet flats are perfect for dressing up black shorts outfits. Style them with a blouse and tailored black shorts for a sophisticated, yet comfortable look. Ideal for a summer brunch or casual work meeting.

Flat Sandals

Flat sandals are perfect for warm days when you want to feel not only comfortable, but stylish. They pair well with jean shorts, linen shorts, and more. Linen shorts in particular are great when paired with flat sandals for a chic beach day outfit idea. Also, if you’re looking for more beach outfit must haves be sure to check out my post here.

Boat Shoes

Boat shoes are another great style to pair with shorts for anything from a beach day, to a boat day, and more! They look great with khaki or chino shorts, giving off a preppy, old money vibe. Style them with a blouse and khaki shorts for a classic, refined outfit. Don’t forget to check out my post on 16 Old Money Summer Outfits if you’re loving this timeless aesthetic.

Penny Loafers

Penny loafers will instantly add elegance to your shorts outfits. They go well with tailored shorts, like black or white ones, for a more polished look. Pair them with a button down shirt and tailored shorts for a smart casual outfit idea. This look would overall, be perfect for a dinner out with friends or a comfortable day at the office.

Heeled Sandals

Heeled sandals are the perfect way to elevate your shorts look, adding a bit of height and sophistication, while still looking summery. They work wonderfully with dressier shorts, like high-waisted or tailored ones. Even leather shorts would be great for a date night look. For more ideas on what to wear with leather shorts, don’t forget to check out my post.

Slingback Heels

Slingback heels are a go to of mine when I want to add elegance to my shorts outfits. They work especially well with tailored shorts or black short outfits, giving a chic and polished look. Pair them with a stylish blouse and tailored black shorts for a sophisticated evening or workwear outfit.


When you want to elevate your shorts look while staying comfortable, opt for wedges. They add comfort and height, making them a great summer shoe. They pair well with jean shorts, linen, cotton shorts, and more adding a casual yet elevated feel. Overall, they are ideal for outdoor events like summer parties with the family!

Thong Sandals

Thong sandals, also known as flip flops, are a summer staple. They go great with casual shorts like cotton or denim. Pair them with a casual tee and cotton shorts for an easy summer outfit. Perfect for beach days or relaxed weekend outings.

Mary Janes

Mary Janes are not only on trend right now, but are also a great way to elevate your shorts looks. Style them with a tucked in blouse and high waisted shorts for a classic, feminine look. Perfect for brunches or even work events this summer.

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Shoes to Wear With Shorts

Check out my latest posts for more chic inspiration!

Please feel free to email me at thegraydetails@gmail.com if you have any questions!  I’m always happy to help with styling or picking out a specific outfit for an event!   Have an amazing day!!

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As always, thank you so much for stopping by today, I truly appreciate all of you! xx, Amanda


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