Best Shoes to Wear with Shorts Reviewed & Rated

We’ve all been there… the weather is beautiful; you have the perfect pair of shorts picked out to enjoy the warmth. You get your outfit together, run to your closet to finish it off with some great shoes only to find… you have no shoes that look good with shorts. Fear not, you aren’t alone.

Last Updated: July 2, 2018
By NicoleH:

Summer is in full swing, and with our latest update, we've added a new classic to the top list of shoes to wear with shorts in 2018. When pairing your new pair of favorite shoes with shorts for thsi summer, think about the style you want to create, and if you want a statement making pair of shoes, or just something casual for BBQs. Be sure to read over our criteria and FAQs section to help you decide on your next new pair!

Even though shoes are at the bottom of our outfit, studies have shown that upon meeting someone new, the most likely thing they will notice about another’s outfit is their shoes. Pants do us the great favor of seamlessly transitioning leg to foot in one, smooth line; shorts can be a bit more difficult. Get a pair of shoes too clunky, and you’ll look like a clown stumbling around town. Get a pair too tight, and you’ll be wishing you left the shoes at home by the end of the day.

Featured Recommendations

Skechers USA Fray Cotton
  • Skechers USA Fray Cotton
  • 4.9 out of 5
    Our rating
  • Foam Base
  • Frayed Edges
  • Price: See Here
Merrell Hollyleaf
  • Merrell Hollyleaf
  • 4.7 out of 5
    Our rating
  • Sandal Style
  • Stylish Comfort
  • Price: See Here
Vans Core Classic
  • Vans Core Classic
  • 4.7 out of 5
    Our rating
  • Patterns and Colors
  • Canvas
  • Price: See Here

So, what are your options? Well, lucky for you we have that taken care of. Don’t think you have to sacrifice style, comfort, or durability when your wardrobe changes from coats and pants to tees and shorts. Below is a list of the top shoes to wear with shorts that will have you strutting around like the beautiful, confident, bare-legged champion you are.


10 Best Shoes to Wear With Shorts


1. Skechers USA Fray Cotton

Sometimes, there is nothing better than a classic. When it comes to pairing shoes with shorts, flip-flops are a tried and true choice. The height of casual, the Sketcher’s USA Fray Cotton Thong offers true comfort and freedom while being the best option to beat the heat. A solid sole paired with a comfortable fabric that hugs the feet, this shoe will look great with shorts without sacrificing comfort.
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Foam-Based Thong Straps
This sandal’s thong straps are made from a soft foam wrapped in canvas fabric that allows the foot to breathe but still offers comfort and support. If you’re looking for a laid-back vibe from your footwear, the Fray Cotton will keep you cool and casual.

High-Grip Outsole
The bottoms of these cotton thong sandals address an issue that many people have with flip-flops: the grip. Wearers can feel confident knowing they can enjoy comfort without sacrificing stability.

Cost and Value
Even though Skechers has produced a high-quality sandal, shoppers do not have to worry about price as this is the most economical option on our list. A low-cost sandal with high reliability makes this a valuable choice for anybody.

Foam Based

Fabric Upper

Frayed Edges

Good Traction


A bit stiff

2. Merrell Hollyleaf

The Merrell Hollyleaf thong sandal is the perfect match for any pair of shorts. Featuring colored canvas and leather uppers and a microfiber-wrapped footbed the Hollyleaf is as fashion-forward as it is comfy. Supportive cushioning and breathable lining, along with a molded sole makes for a comforting wear, while their toe-thong design and subtle floral pattern make these Merrell sandals a must-have for warmer weather. For added style, the Hollyleaf has stitching detail and an interloping rope accent, along with a one-inch heel and super-cute toe-ring thong style.
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Toe-Ring Thong
Not your regular thong sandal, the Hollyleaf is a uniquely styled toe-ring thong which features a wraparound toe-ring instead of the traditional Y-shaped thong. This style of thong offers a more secure fit and poses less risk of rubbing than the Y-shaped strap between the toes.

These Merrell thongs are all about comfort! They feature supportive cushioning, breathable lining, and a molded sole that conforms to the shape of your foot providing customized comfort for every step. You will never have to worry about tired or achy feet again thanks to the Hollyleafs' incredible wearability.

Cost & Value
The Merrell Hollyleaf is a relatively lower-priced choice so you won't have to spend a fortune to find a pair of shoes that are going to look great with your favorite shorts. Comfort and style all wrapped into one uniquely styled pair of thongs.
  • Toe-Ring Thong
  • Contoured Microfiber Footbed
  • Cushioned 
  • Colored Canvas & Leather Uppers
  • Easy On & Off 
  • Straps Are Not Adjustable

3. Merrell Jungle Moc

A great shoe for working, exploring, or just getting out in nature, the Merell Jungle Moc Slip-On is a high-quality option meant to handle the rigors of the outdoors. Weather-proof and composed of pig suede leather, this shoe is among the most durable on our list. The trim and athletic design make it a great option for the more adventurous shoppers.
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Weather-Proof Materials
This shoe is composed of weather-resistant leather, making it perfect for any conditions. You’ll be able to explore creeks and lakes, take these to the beach, even learn how to paddleboard should you so choose!

Air-Cushion Midsole
A padded air-cushion situated in the midsole offers additional support and comfort for the foot – ideal for walking on rougher terrain. Each step will have you closer to reaching the perfect summer picnic spot or simply spending the day exploring the city.

Cost and Value
The cost of this shoe reflects the high-quality materials and durable build, but it is well worth it. Meant to endure harsh conditions and long-time wear, you can be sure that this purchase will be valuable for a long time. Ideal for summer hikers or other outdoor enthusiasts, but also great for days out on the town!

Weather-proof leather

Long-term use

Easy slip on/off

Amazing comfort


Arch support can be too high for some wearers

Sole separation at back of shoe

4. Converse Chuck Taylor All Star

4. Converse Chuck Taylor All Star
Gone are the days when these shoes were worn by old basketball players in short-shorts, the Chuck Taylor All Star has found a place with every generation since its inception, and today is no different. Widely held as a classic shoe option, Chuck Taylor’s are a great choice to pair with the right shorts. The perfect mix of casual and athletic, you can wear these from the classroom to the skate park (just maybe not on the basketball court so much these days).
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Durable Canvas
Part of the charm of the Chuck Taylor All Star is its dependability. A deceptively simple design, these shoes are built with quality canvas that can hold up to even rigorous activity. And, should you need to clean these, simply throw into a pillowcase and into the washer on the gentle cycle, which can help keep them looking and smelling new!

Brand Recognition
No matter where you go, you’re likely to see someone rocking a pair of Chuck’s. This shoe offers a unique style that makes a statement in any environment. From lifting in the gym to casual walks, or out for a concert or summertime festival, they’re a statement-making iconic shoe everyone loves. With the variety of colors available, you’ll be able to find one to be your next favorite pair to rock with shorts!

Cost and Value
A simple design paired with a strong brand recognition has kept this shoe at a very reasonable price point – as it has been for most of its existence. If you’ve not yet had a chance to invest in a pair, there is never a better time than now, especially as summer is in full swing. Try them out at your next big BBQ!

Extremely multi-functional

Great option for the gym

Excellent quality materials

Easily machine-washable


Narrow around the foot

Offers less support than other options

5. Skechers USA Expected Avillo

5. Skechers USA Expected Avillo
Skechers finds itself on our list again with their USA Avillo Slip-On Loafer. While also a slip-on option, this shoe is a sturdier option than the flip-flop. Loafers perfectly mix comfort with usability and are great for the on-the-move individual. An easy slip-on fit, you’ll be amazed at how much you are able to accomplish in these shoes – all without sacrificing style.
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Padded Collar for Ankle Comfort
A common failing of loafers is their tendency to rub uncomfortably on the ankle. The Avillo Slip-On Loafer has a padded ankle-collar, ensuring maximum comfort throughout the day. Say goodbye to upper ankle blisters from all day wear, and hello to the freedom to stroll about your favorite summertime festival in comfort.

Extra Wide
This shoe has an extra-wide build that makes sure all wearers find it comfortable. The breathable fabric combined with the wide build allows the shoe to form to the feet of anybody. Perfect for those who may need to think about allowing room in their footwear, such as those with Morton’s Neuroma, where restrictive footwear can exacerbate a medical foot condition.

Cost and Value
Slightly costlier than the sandal, the loafer is still a very affordable option for the casual shoe shopper. It’s perfect for those with wide feet or other foot ailments that require roomier toe boxes. A common choice for shorts-wearers everywhere, and sure to please!

Great look with no laces

Dependable long-term option

Great for all ages

Works with or without socks


Retains foot odors

Tend to run small for fitting

6. Birkenstock Arizona Milano

6. Birkenstock Arizona Milano
With this shoe, Birkenstock has done the near-impossible: they have made a classy-looking sandal. With high-quality materials and a simple yet effective design, the Arizona Birkibuc Sandal is a favorite of many. Birkenstock is renowned for the comfort and stability of their shoes, and this model is no different. The rare sandal that you are able to wear all day comfortably, you can also boast a timeless design that wears well with a wide-range of clothing options, especially shorts.
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Contoured Cork Footbed
Designed to form to your foot over time, the cork footbed is a sole that grows even more comfortable over time. This means there is some break in required before the Milano truly feels like you’re walking on air, but it’s worth the time spent. These shoes are meant to last long-term, with their durable footbed and overall design.

Shock Absorption Sole
Not only designed to form to your foot, the sole of the Arizona Birkibuc Sandal also is able to absorb jarring landings much better than other sandal options in the market for top comfort. If you’re concerned about heel pain or need arch support, Birkenstock has you covered with the structural design of the footbed combined with shock absorbing sole.

Cost and Value
Birkenstock’s generally run at a higher price than the average shoe in the market, but they are highly customizable and designed to fit your unique foot perfectly all while lasting for many years. Birkenstock prides their footwear on comfort designed from the natural mold of a foot, and the Milano won’t disappoint. The cost may be higher, but the quality is unparalleled.

Comfortable even for long-distance walking

Longer life than average shoes

Can be worn casually or with an outfit

Fit uniquely to your foot


Complicated sizing structure

Take some time to break in

7. Dunham Captain Boat Shoe

7. Dunham Captain Boat Shoe
The boat shoe is a classic option that has gained steam over the past decade. Dunham’s Captain Boat Shoe is the typical iteration of this model, with a leather body, laces stretched over the top, and a solid rubber sole. Suitable for a cocktail party on the water or just running errands, the Captain Boat Shoe is a reliable option that mixes class with usefulness.
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High Quality Leather
This shoe is made from high-quality leather that allows your foot to breathe while molding to its shape. An example of the rare shoe that gets better the more you wear it. Also more durable than other materials such as mesh or textiles, you’ll be able to keep these for quite some time to come. Be sure to take care of the leather to extend the lifetime of the shoe.

Removable Memory Foam Footbed
The Captain Boat Shoe has a removable memory foam footbed that ensures maximum comfort that lasts over time. And, should you need custom orthotics, it’s an easy task to remove the footbed and replace. Great comfort for when you plan to be standing aboard an afternoon fishing excursion.

Cost and Value
Because this shoe is made of leather, it has a slightly higher price point than some of the other options. But, the benefits of this shoe being a classier option, combined with the comfortable build, makes it a cost-effective purchase. And with its styling, it’s a perfect shoe to compliment any pair of shorts!

Great for hard-to-fit feet

Comfortable for wide feet

Great looking ‘formal’ option

Won’t slip in wet areas


Shallow depth can cause fit issues

Not water-proof

8. Adidas Originals Seeley

8. Adidas Originals Seeley
The Adidas Originals Seeley Skate Shoe is the classic Adidas look. Three solid stripes down the side with a solid background all on a sleek design has made this a popular shoe choice for years. A classic two-toned look, this shoe has it all: comfort, appearance, quality. Whether you want to look fresh or feel great, these shoes work great on just about anybody.
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Abrasion Resistant Material
The upper portion of the shoe is composed of abrasion resistant material – meaning your shoes will stay looking great even after you’ve broken them in. You can feel free to wear these about town, off trail, even play a spontaneous game of soccer without worrying about scuff marks.

Vulcanized Rubber Outsole
The outsole of this shoe offers surprisingly strong grip, making this shoe not only a great looking model but a stable one as well. If you’re an avid skater or BMX trickster, you’ll love the feel of these on the board or bike. And even if you’re not, they still have an iconic appeal that will catch compliments.

Cost and Value
This shoe is priced among the middle of the pack, making it a great deal for the casual shoe-wearer. You can know that the cost of the purchase is going to a shoe that will last you a long time and maintain its look.

Abrasion resistant material


High grip outsole

Comfortable build


Don’t breathe well for long use

Too narrow for wide feet

9. Vans Slip-on Core Classics

9. Vans Slip-on Core Classics
Vans is a brand you can’t go wrong with when it comes to laid-back casual styling. Becoming quite popular in the 1970s through to 1990s, it’s still a go-to classic brand for lace-ups, high tops, slip on, and skater or BMX enthusiasts. The Core Classics is a slip on version of their classic design, available in patterns and colors galore, so you’ll be sure to find one suited to your individual style tastes.
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Vans Slip-on Core Classics come in a variety of colors, patterns, and statement-making designs that will have these shoes getting nods of approval when paired with shorts. Checkered patterns give some fun retro feel to your outfit, while a simple neutral color can pair well with bright colored shorts or shirts. Slip-on design keeps it looking casual and relaxed, which can be perfect for BBQs, game night, or just out and about in town.

Thick soles keep these Core Classics springy to the step and pad your feet in plush comfort. Its easy slip-on design makes them a breeze to get on and off, and a padded collar helps keep blisters at bay. Elastic along the tongue maintains the fit of the shoe keeping it snug to your foot. The low cut design also allows ankle movement and flexibility in case you decide to take these for a spin on the board or bike.

Cost and Value
Depending on which color or pattern you choose, these can vary in price, but by no means are expensive for a great pair of shoes. Van’s comfortable slip-on keeps your look casual, but funky patterns can help make a statement if you prefer. With such variety, you can dress up a pair of boring shorts, or dress down a colorful short. Core Classics are a great addition to anyone’s collection!
  • Slip On
  • Iconic
  • Patterns and Colors
  • Breathable
  • Comfort
  • Durability

10. Keen Bali

10. Keen Bali
The Keen Bali is a top-selling slip-on that pairs perfectly with any style of short. Complete with a metatomical footbed that provides an internal support system that gives excellent arch support and cradles the foot for superior comfort. The Bali's slip-on design makes for easy on and off wearability, and a non-marking rubber outsole offers grippy traction on any surface. A hydrophobic mesh lining and polyester webbed upper make these Keen's a great choice for warmer weather and is sure to look stylish with all kinds of shorts and summer outfits.
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Slip-On Design
The Bali has a slip-on design which makes for super easy on and off wearability and they looks as stylish as they are comfortable making the Bali a perfect pair of shoes to wear with your favorite shorts. With adorable styling found in the webbing, it gives an Indonesian feel to your next look.

Hydrophobic Lining
Keen's Hydrophobic lining is a lightweight material that keeps your feet cool and dry by allowing moisture vapor to pass through its open-cell structure and away from your foot. Feel free to rock these on hot days, or take for a stroll around the creek or pool.

Cost & Value
The Keen Bali is a mid-priced option and should definitely be a strong consideration when buying shoes to wear with sandals. The Bali's slip-on design and metatomical support system offer unparalleled comfort and support, while the non-marking rubber sole gives excellent traction on both wet and dry surfaces.
  • Metatomical Internal Support System
  • Non-Marking Rubber Outsole
  • EVA Molded Footbed
  • Good Traction
  • Hydrophobic Mesh Lining
  • Narrow At Toe

So, hopefully you’re feeling a bit less worried about pairing the perfect pair of shoes with the shorts piled up in your closet. When it comes to pairing shoes with shorts, you really don’t have to break the bank to find something that will shoot your confidence up and your foot pain down. There are a ton of options out there, whether you want to focus on comfort, style, or durability – it is just a matter of finding what works best for you. Don’t be afraid to try something new. Pick out some great shoes, lace them up (or slip them on) and go about your business knowing that you look awesome.


Criteria Used To Evaluate The Best Shoes To Wear With Shorts


Who doesn’t love the summer? The warm sunshiny days, the long strolls along the beach, the cute summertime outfits, including your favorite pairs of shorts… But one sure-fire challenge can be finding a pair of shoes that actually look good with shorts. The wrong shoes can make your feet look too big or just make you look ridiculous, plain and simple.

So what type of shoes can you wear to look stylish all summer long? Firstly you need to know the basics, what the different styles of shoes to wear with shorts are.

  • Ballet Flats: The classic that never goes out of style, the ballet flat. Ballet flats are a slipper-like shoe that has the appearance of being without a sole. They are dainty, cute, and look oh-so-great with shorts.
  • Sandals: Everyone loves a good pair of sandals! Sandals are an open and airy type of shoe that attaches the shoe sole to the wearer’s foot with either a strap, an open upper, or a mesh-like material. In general, most sandals will look good when paired with shorts, after all, that is what they’re made for.
  • Flip-Flops: Flip-flops are an even more relaxed type of sandal where the sole attaches loosely on the foot with a y-shaped strap. Flip-flops are a great choice of shoe to wear with shorts so long as you’re not planning on walking long distances or engaging in sports. Flip-flops offer little in the way of support and offer even less protection for your feet, which is why prolonged walking or playing sports in flip-flops is not advisable.
  • Loafers: Loafers are a relaxed shoe for summer that has no laces or fastening system. What could be better than simply slipping on your shoes and heading out the door? Loafers usually have a low-heel, or completely flat heel and can be worn by a man, woman, or child. There are both casual and dressy loafers which makes them a great option for pairing with a more business style short for summer days spent at the office.
  • Canvas Sneakers: Canvas sneakers are always stylish and fun for the summer. Not only are canvas shoes super-breathable and airy, but they also look great with a pair of shorts. Wearing a pair of canvas sneakers with your favorite shorts will make for a relaxed and casual, yet stylish and fashionable look. Canvas shoes are quite versatile and can be worn for walking, beaching, or even for business.
  • Boat Shoes: With the warmer weather comes the time for boating and nothing will make you look more stylish while you sail than a pair of boat shoes. But they’re not just for boating they look great with shorts no matter where you are.
  • Espadrilles: Espadrilles can be a flat, high-heel, or commonly a wedged platform. They are made with a canvas or cotton upper and the sole is made of esparto rope. This type of shoe never goes out of style and always looks great with a pair of shorts. Men, women, and children can all look great while wearing a great pair of espadrilles.



It can be tough to find a shoe that will look good when worn with a pair of shorts that is also going to keep your feet comfortable. Flip-flops, for example, is a popular choice to wear with shorts but can be uncomfortable and offer little-to-no-support.

Luckily, there are tonnes of features available with shoes that can help to keep your feet comfortable even during warmer temperatures. Some of the key comfort features to look for are:

  • EVA Cushioned Midsole: EVA is a lightweight man-made material that offers great cushion, flexible comfort, and airy breathability.
  • Contoured Footbed: This type of footbed is designed so that it contours to the shape of your foot providing excellent support and a customized wear.
  • Padded Arch Support: The arch of the foot can cause all sorts of aches and pains if it is not properly supported which is why a padded footbed can be very important. If you suffer from plantar fasciitis this can be particularly important.
  • Rubber Outsole: Rubber is an airy and lightweight material that also offers superior traction so it is grippy even on wet surfaces.


Having a shoe that is breathable and airy is important during warmer weather because just as you wear shorts to stay cool, your feet also need to cool off when it’s hot. There are certain materials that are much more suited for wearing in the summer than others, materials like; canvas, mesh, linen, viscose, and even leather-lined shoes, will all have good airflow and allow your feet to breathe.

Whereas, materials like polyester and acrylic have poor ventilation and will make your feet sweat. Sandals and open-toed shoes are, of course, another airy choice of shoes to wear with shorts and they’re often made of light materials like mesh, or have a leather-lined insole and straps.

Odor Control

Shoes that are worn with shorts are usually more susceptible to odors because the weather tends to be warmer when people opt for wearing a pair of shorts. Warm weather causes our feet to sweat and moist areas are the perfect breeding ground for bacterias and mildew and once bacteria begins to grow odors aren’t far behind!

There are, of course, odor controlling products like powders, sprays, and gels that can be bought separately from the shoe, but why spend extra money on a secondary product when you can have a shoe with built-in odor control?!

There are several different odor controlling technologies that are applied during the manufacturing of a shoe, but three of the best are;

  • Cleansport NXT™ – Cleansport™ technologies use probiotics as a natural method of odor control. The process involves the use of beneficial microbes that are bonded to the surface of the shoe’s fabric that end result is natural, non-toxic odor control.
  • Microban®  – Microban® treated shoes offer the wearer benefits such as, preventing sweat, odor and mildew prevention and eliminating odors. Microban® treatments utilize antimicrobial odor control technologies to capture and prevent bacteria from multiplying and creating smells. These treated materials are subjected to customized experiments to simulate the actual intended use, including; wearability tests, repeated laundering tests, and shower simulators, to ensure totally product efficiency.
  • Aegis® – Aegis provides a microbe shield against bacteria, mildew, and odor by enhancing the fabric of the shoe and creating active antibacterial action. Aegis relies on a micro polymer coating, which eliminates bacteria, mold, and fungus on contact, it contains no chemicals and is effective for the entire lifespan of the shoe.

Frequently Asked Questions


Q: Can I wear socks if I have shorts on?
A: Socks and shorts don’t typically look good together, but there are a few styles of sock that can be fashionably worn with shorts. Invisible socks, for example, are your best option because they’re, well, invisible. Be sure to purchase invisible socks that have rubber on the back to prevent them from sliding down your foot.

Q: What about shoes for longer shorts, like the ones to the knee?
A: The shoes on our list tend to be well-suited for shorts of any length so they will look good with both longer and shorter ones.

Q: How can I find a comfortable pair of shoes to wear with shorts that aren’t going to hurt my feet?
A: The shoes on this list are highly rated for comfort and will keep your feet feeling great all day long. Some key features to look for in a shoe are; a padded and contoured footbed, supportive outsole, and adequate protection. It is also important that a shoe allows proper airflow around the feet and toes to prevent sweating. When your feet sweat, they slide around in your shoes which can cause rubbing and blisters. Without proper support and cushioning your feet can become tired and fatigued at the end of the day.

Q: Are thong sandals really bad for your feet?
A: Yes and no. Most thong or flip-flop sandals are seriously lacking in both support and cushioning which can be detrimental to your feet. There are, however, lots of thongs that are well-made and offer additional support and cushion where it’s needed the most. There are several options on this list that are comfortable and stylish that definitely won’t hurt your feet


  1. SCOTT CHRISTIAN, 10 Shoes Every Guy Should Have for Summer, Article, Jun 30, 2017
  2. PRIYA RAO, Every Single Type of Shoe You Need for Summer, Article, May 07, 2017
  3. The Idle Man, 5 Perfect Shorts & Shoes Combinations, Article, Feb 01, 2018
  4. Fashionbeans Editors, The Right Shoes to Wear With Shorts,
  5. Hannah Clare, 5 Perfect Shorts and Shoes Combinations,
  6. On Point Fresh, How Men Should Wear Shorts,
  7. On Point Fresh, Men’s Summer Fashion – Latest Trends In 2018,

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