What Are The Best Shoes To Wear With Shorts | 2021 List

What Are The Best Shoes To Wear With Shorts | 2021 List

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Olyvia Smith

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Shorts are the epitome of casual fashion. After all, nothing quite beats the feeling of a cool breeze brushing against your legs when you wear shorts in hot weather.

Additionally, shorts are highly versatile; you can wear them on several occasions, be it a beach day or a Sunday brunch.

But arguably, the best thing about shorts is that you can style them with almost any shoes, and you’ll still end up looking good. Between flip-flops, dress shoes, crocs, sneakers, and waterproof footwear, you can make pretty much anything work with shorts.

Heck, shorts can even make socks and sandals look good, which is saying a lot.

However, having so many options makes it that much more challenging to make the right choice.

But don’t worry, because we’re here to choose for you! So, let’s cut a long story short and take a look at the best shoes you can wear with shorts.

1.  Loom Waterproof Sneakers

Loom Waterproof Sneakers 


  • Best waterproof footwear for running
  • Black and white minimalist design
  • Highly breathable
  • Lightweight material

People typically wear shorts for athletic purposes, be it working out, going for a run, or hiking in the woods. Of course, this makes sense since shorts give you the flexibility and range of motion that you need for athletic activities.

So, what better shoes to wear with athletic shorts than equally flexible waterproof footwear?

Loom waterproof sneakers are a game-changer for people who like to stay physically active. The selling point of these knit shoes is their 100% waterproof outer layer, which keeps your feet safe from unexpected puddles and heavy rainfall.

Shoe Anatomy 

But unlike most waterproof footwear, Loom sneakers boast unprecedented levels of breathability. Moreover, thanks to their knit construction and premium Merino wool interior, these shoes are the perfect complement to those hot, humid summer days.

Moreover, you’ll find that the Loom sneakers are just as comfortable as your shorts, if not more. These shoes maximize comfort and prevent unnecessary strain on your feet, ankles, legs, and back with an extensive cushioning system.

As far as their style goes, Loom sneakers boast a minimalist design. Their black-and-white exterior gives them a sleek and modern appeal, and you can easily pair the color combination with any outfit.

100% Waterproof Shoes

2.  Chuck Taylor All Star High Tops

 Chuck Taylor All Star High Tops


  • Best shoe for casual wear and weightlifting
  • Timeless high-ankle silhouette
  • Lightweight and breathable canvas upper
  • Extremely durable with a long lifespan

The key to styling shorts, or any other outfit, is paying attention to proportions and overall balance. The rule goes that if your outfit is light on the top, then it needs to be bulkier from the bottom, and vice versa.

So, since your shorts typically cut off above the knees, you can balance your overall outfit by wearing shoes covering your ankles. That’s precisely where the Chuck Taylor All Star High Tops come in.

The Chuck Taylor All Star High Tops, also known as the Converse All Stars, are tried and tested sneakers that have stood the test of time. Created in the 1920s, the All Stars have hardly changed in nearly a century, a testament to their solid design.

The shoe’s upper material is made from an extremely lightweight and breathable canvas that enhances the airflow through medial eyelets in the shoes. Be warned, though: the shoe is not waterproof, so you’ll be better off wearing waterproof footwear in rainy areas or muddy terrain.

This design has also helped the shoes expand beyond their original use case as basketball shoes. Nowadays, you can wear the All Stars from anything ranging from casual wear to weightlifting.

After all, what better shoe to pair with shorts than one designed specifically for a sport where the players wear shorts?

3.  Sperry Sea Kite Sport Moc Boat Shoe

 Sperry Sea Kite Sport Moc Boat Shoe


  • Best waterproof footwear for boating and fishing
  • Adaptive Wave-Siping™ technology
  • Water-resistant mesh upper linings
  • Removable EVA footbed
  • Quality leather build

What’s the first thing that comes to your mind when it comes to boating? Is it going fishing with your old man? Perhaps it’s sailing on a luxury yacht? Or maybe, canoeing on a calm lakeside?

No matter what the case is, shorts are a popular clothing choice for any boating activity. The reason? They help you dry off much quicker than a pair of pants or trousers. As such, you’ll also need a pair of boating shoes to pair with your choice of shorts before you go boating.

So what better choice when it comes to boating shoes than the Sea Kite Sport Moc Boat Shoe?

Whether it’s leather material, non-marking rubber soles, or a siping pattern on the soles for wet deck grip, the Sea Kite Sport Moc Boat Shoe has everything a decent boating shoe needs.

Patented adaptive Wave-Siping™ technology and water-resistant mesh upper linings help make this shoe the ideal candidate for boating. The shoe’s compression-molded EVA footbed is also fully removable for maximizing your underfoot comfort.

Now available in a brand new sporty look, the Sea Kite Sport Moc boasts the prestige of the original Sperry leather boat shoes with added flair and functionality.

4.  Croc Classic Clog

 Croc Classic Clog


  • Best waterproof footwear for a beach day
  • Incredibly lightweight
  • Ventilation ports for breathability and wicking moisture
  • Quick-drying and easy to clean
  • Available in 26 different colors

Now before you rush to grab your torches and pitchforks, hear us out first.

Like many on the internet, you might believe that crocs are unfashionable, tacky, or even cringey. But, regardless of your opinion on Crocs, it’s hard to deny one thing: The Croc Classic Clog might just be the best waterproof footwear for the beach available today.

Now, why is that so, you may be wondering? Several reasons. For one thing, the Croc Classic Clog is exceptionally lightweight, weighing only a couple of ounces. It is also a quick-drying, easy-to-clean shoe, both of which help when you’re at the beach.

The shoe is also waterproof and breathable, having several ventilation ports. The ventilation ports not only help with breathability but also with shedding any debris such as beach sand. After all, what’s more annoying than having sand stuck in your regular beach flip-flops that you can’t seem to remove?

The Croc Classic Clog is available in 26 different color options, making it easy to pair with your board shorts or swimming trunks on a beach day.

Also read: The Best Barefoot Shoes for Walking or Running


5.  M. Gemi Sacca

 M. Gemi Sacca


  • Best loafers for casual wear
  • Unlined interior for breathability and flexibility
  • Durable suede build
  • Handcrafted in Tuscany, Italy

From cargo to denim, shorts encapsulate the casual look in all their forms. Similarly, loafers are the smart casual shoe choice for everyday wear. So naturally, pairing both together makes for an excellent smart casual fashion combination.

While there are many high-quality loafers on the market to pair with your shorts, none steal the thunder quite like The Sacca by M. Gemi.

Unlike cheap loafers made from faux suede, The Sacca has a natural suede upper. The sand-colored suede upper also makes the shoe highly durable, in addition to looking gorgeous.

The interior of the shoe is also unlined, with a leather footbed. This interior makes the shoe not only breathable but also highly flexible. The leather sole also adds to the overall flexibility of the shoe.

The best part? The Sacca is handcrafted in Tuscany, Italy, and has a genuine moccasin construction. That said, the Moccasin build is also a double-edged sword; combined with the shoe’s high vamp, it makes the shoe non-waterproof footwear.

All in all, If you love handmade, authentic Italian shoes at an affordable cost, you’ll be hard-pressed to find a better bargain than The Saccan. To best pair with shorts for a sophisticated yet casual look, we recommend skipping socks entirely with this shoe.

6.  Birkenstock 1774 Arizona Croco

 Birkenstock 1774 Arizona Croco


  • Premium leather sandals
  • 1774 Birkenstock logo printed
  • Embossed leather Croco upper
  • Cork latex footbed
  • Nappa leather insole lining

So far, we’ve looked at premium shoes like The Sacca by M.Gemi. We’ve also seen reliable shoes that have been around for over a century, like the Converse All Stars. If you’re a fan of both, you’re in for a real treat with the Birkenstock 1774 Arizona Croco.

Founded in 1774 by German shoemaker Johann Adam Birkenstock, Birkenstock has since become one of the world’s most successful and prestigious shoe companies.

Sure, you may find Crocs tacky, but you’ll think twice before saying the same for the 1774 Arizona Croco. As a matter of fact, we’re almost embarrassed putting the two in the same sentence; after all, Birkenstock shoes are in a league of their own.

It is no secret that this shoe’s luxurious appeal is the reason why many buy it. That’s why you’ll be delighted to know it comes printed with a 1774 Birkenstock logo, as well as an exclusive 1774-design shoebox and dust bag.

It’s not just luxury that the Birkenstock 1774 Arizona Croco is known for, though; the shoe’s signature slim Nappa leather insole and cork leather footbed offer a good mix of both comfort and versatility. As such, you can pair these sandals with almost any pair of shorts.

As the saying goes: If it ain’t broken, don’t fix it. That’s why the Birkenstock 1774 Arizona Croco brings back the original 1774 design of the shoe from the days of Birkenstock himself.

7.  Skechers Bobs Breeze for Women

 Skechers Bobs Breeze for Women


  • Perfect alternatives for flip flops
  • Extremely breathable and lightweight
  • Beach shoes

Whereas shorts are the ultimate summer clothes, espadrilles are the ultimate summer footwear. These Skechers Bobs Breeze are perfect for anyone looking to have a comfortable, breezy summer.

These chunky canvas shoes are great for pairing with shorts. The platform heel not only balances out your proportions but also gives you a little extra height. Moreover, the hefty soles are perfect for today’s trends of campy footwear.

In terms of performance, the soles are noticeably flexible and lightweight. This allows you to take each step with confidence as the sole bends according to the natural movement of your feet.

Moreover, the soft and breathable canvas upper is the perfect material for those insufferable summer days. When the sun is beating down and the humidity is off the charts, the Bobs Breeze will stay true to their name and ventilate your feet.

However, the most notorious feature of these shoes is their memory foam midsole. Essentially, the memory foam helps distribute your weight equally across your whole foot. This, in turn, ensures that you don’t develop pain hotspots as you stand on your feet the whole day.

Frequently Asked Questions


Here are the answers to some frequently asked questions that will help you pick the best shoes to pair with shorts.

Which Shoes Look The Best With Shorts?

Shorts are versatile, which means that they can go well with almost any type of shoe. Sneakers, loafers, boat shoes, crocs, flip-flops, leather sandals, and espadrilles will all work depending on the occasion and types of shorts you wear.

Should You Wear Socks With Shorts?

Socks are always essential when you wear closed shoes to prevent foot odor and bacteria buildup. But when it comes to shorts, you should try to wear short socks so your socks remain hidden. Of course, sneakers are an exception to this rule and you can definitely wear long socks or crew socks with sneakers.


Finding the right pair of shoes to pair with your shorts may seem intimidating at first. After all, there are so many different shoes to choose from these days.

That said, as long as you know what you need the shoes for, it’s relatively straightforward to pair them with your shorts.

So whether you’re spending a day at the beach, an afternoon fishing, or just need some waterproof footwear for a hiking trip on a rainy day, you can always find a shoe to pair with your shorts.

Just try out one of the options on our list above, and you’ll be making smart fashion choices in no time!

You may also like: 10 Best Halloween Custom Shoes Ideas


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Olyvia Smith


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