Best Shoes to Wear with Shorts Reviewed

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.

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
 
Converse Chuck Taylor All Star
  • Converse Chuck Taylor All Star
  • 4.5 out of 5
    Our rating
  • Canvas Upper
  • Gusseted Tongue
  • Price: See Here
 
Vans Classic Skate
  • Vans Classic Skate
  • 4.5 out of 5
    Our rating
  • Simple Low Top
  • 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 10 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.

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 economic option on our list. A low-cost sandal with high reliability makes this a valuable choice for anybody.
Pros

Excellent value

Lasts longer than most sandals

Form to your foot for maximum comfort

Stylish

Cons

Hard sole for sensitive feet

Fraying threads at joint of thong

2. 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.

Brand Recognition
No matter where you go, you’re likely to see someone rocking a pair of Chuck’s. This shoe offers unique style that makes a statement in any environment.

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.
Pros

Extremely multi-functional

Great option for the gym

Excellent quality materials

Easily machine-washable

Cons

Narrow around the foot

Offers less support than other options

3. 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 is 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.

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.

Cost and Value
Slightly costlier than the sandal, the loafer is still a very affordable option for the casual shoe shopper. A common choice for shorts-wearers everywhere.
Pros

Great look with no laces

Dependable long-term option

Great for all ages

Works with or without socks

Cons

Retains foot odors

Tend to run small for fitting

4. Dunham Captain Boat Shoe

4. 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. The rare shoe that gets better the more you wear it.

Removable Memory Foam Footbed
The Captain Boat Shoe has a removable memory foam footbed that ensures maximum comfort that lasts over time.

Cost and Value
Because this shoe is made from 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.
Pros

Great for hard-to-fit feet

Comfortable for wide feet

Great looking ‘formal’ option

Won’t slip in wet areas

Cons

Shallow depth can cause fit issues

Not water-proof

5. Merrell Jungle Moc

5. 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 makes 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.

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.

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.
Pros

Weather-proof leather

Long-term use

Easy slip on/off

Amazing comfort

Cons

Arch support can be too high for some wearers

Sole separation at back of shoe

6. Birkenstock Arizona Birkibuc

6. Birkenstock Arizona Birkibuc
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. These shoes are meant to last long-term.

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.

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 to your unique foot perfectly all while lasting for many years. The cost may be higher, but the quality is unparalleled.
Pros

Comfortable even for long-distance walking

Longer life than average shoes

Can be worn casually or with an outfit

Fit uniquely to your foot

Cons

Complicated sizing structure

Take some time to break in

7. Vans Classic Skate

7. Vans Classic Skate
Beloved by skaters everywhere, Van’s are no longer a niche shoe. Having broken into the mainstream, you can find just about anybody wearing Van’s these days. The classic Skate Shoe model was made to be worn with shorts. Laces tied, untied, or sans laces at all, this is a unique and efficient shoe that looks great with a pair of shorts.
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Highly Customizable
Available in a variety of color and texture options, this shoe has evolved to have many variations over the years. There is even the option for personal customization to give your shoe a truly unique feel.

High Quality Canvas
Built with high quality canvas, this shoe adapts to the shape of your foot over time while allowing it to breathe.

Cost and Value
A low-cost option, the Vans Skate Shoe is a great value. This shoe is also known to last, so you can be sure that the price you pay will be well worth it.
Pros

Classic appearance

Highly customizable

Wear in to shape of foot

Long-term wear

Cons

Heavy shoe

Lace eyelets can tear

8. Nike Air Jordan 1

8. Nike Air Jordan 1
There really isn’t much to be said about Jordan’s that hasn’t been discussed tenfold already. A great shoe with a world-wide brand, the Nike Air Jordan 1 is the epitome of the Jordan shoe. The classic high-top Nike design is eye-catching without being too flashy and the leather and rubber materials offer top-level comfort.
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Solid Rubber Outsole
The solid rubber outsole with deep grooves allows for maximum comfort and grip, whether you are playing ball or just walking around.

Air-Sole in Heel
A built-in air-sole in the heel provides additional comfort and support for athletic movements. This shoe is built to withstand high-level movement while providing great feel.

Cost and Value
When you buy a pair of Jordan’s, you know you are paying for the name. However, between the overall visual attractiveness of the shoe, the comfort and support it provides, and the athletic capabilities, this is a very valuable purchase.
Pros

Air-sole in heel

Solid rubber sole with top-level grip

Great appearance

High-quality materials

Cons

Large shoe

Peeling at bottom of sole

9. Adidas Originals Seeley

9. 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.

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.

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.
Pros

Abrasion resistant material

Multi-functional

High grip outsole

Comfortable build

Cons

Don’t breathe well for long use

Too narrow for wide feet

10. Timberland Icon 3-Eye

10. Timberland Icon 3-Eye
A hearty, well-built shoe, the Timberland Icon Three-Eye is a favorite of those who want the durability of a boot but the freedom of a shoe. Made of high-quality leather, this shoe has a highly ridged sole, making it great for rougher terrain. The leather of the shoe molds to the wearer and is built to last for a long time.
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High-Ridge Rubber Sole
Similar in appearance to a boat shoe, this model is heftier and more durable. The high sole ridges allow the wearer to feel confident walking on rougher surfaces.

Leather Lining and Footbed
While other shoes may only use leather for the upper part of the shoe, this Timberland uses leather for the lining and footbed, allowing for maximum comfort and quality.

Cost and Value
This shoe is made of very high-quality materials and the price is reflective of that. The value is high however, as you can expect them to last for years without losing their shape.
Pros

Can handle rugged terrain

Casual appearance for everyday wear

Long-lasting

Versatile

Cons

Too shallow for some inserts

Narrow build

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.