Boots are one of the most versatile types of shoes. They can be worn with jeans or skirts and even shorts. But, there are some boots that are more suitable than others for wearing with shorts.

Below, we’ve rounded up some of the best boots you can wear with shorts.

The Chelsea Boot

The Chelsea boot is a classic boot style that was originally worn by British soldiers in the 19th century. It’s a short boot that comes up to just below your calf, making it perfect for wearing with shorts. The Chelsea boot comes in black, brown and tan colors and can be found in both leather and suede options.

The Ankle Bootie

Ankle boots have become very popular recently due to how comfortable they are to wear all day long. Ankle boots come in a wide range of styles including flat, heeled and wedge heels as well as different heel heights such as 1 inch or 2 inch heels. A great thing about ankle boots is that many styles come with zips on their sides so you can put them on without having to bend down too much or struggling with buckles! Ankle boots can be worn with jeans as well as shorts but make sure that you choose ones that aren’t too high-waisted –

Casual Shoes To Wear With Shorts

When it comes to must-have wardrobe items for men, shorts are cool and comfortable clothing that work for many occasions. While most guys love these versatile garments, picking the right shoes to wear with shorts can be daunting. To create a fashionable ensemble, you’ll need to find a combination of shorts and shoes that fits your style and complements your outfit. Whether you’re dressing up for date night in the summer or want a smart casual outfit on vacation, there are several types of shoes that look good with shorts.

Some men will pair casual shoes like trainers and espadrilles with cargo shorts and a polo shirt for a relaxed look, while others may prefer dressy footwear like loafers and boat shoes with chino shorts and a button-down shirt for a smart classy style. With so many different shoe styles to consider, it can be a challenge choosing the right footwear to go with shorts.

To inspire you with ideas, we’ve compiled this guide on the best shoes to wear with shorts. From sneakers and high tops to loafers and dress shoes, explore the different ways to style men’s shoes with shorts for a stylish look.

Shoes To Wear with Shorts

Casual Shoes

You can wear casual shoes with shorts to create a relaxed and stylish look. When styling trainers, sneakers, espadrilles and other casual men’s footwear, it’s important to keep your outfit fresh and on-point if you want to pull off the right aesthetic.

For a comfortable and modern style, you can pair athletic footwear with jogging shorts and top the ensemble off with a designer t-shirt, black Havana hat and cool sunglasses. Whether you’re going to the beach or having a brunch date, this trendy streetwear look can work all around town. You can also go with fashion sneakers, khaki shorts, a lightly woven henley shirt and a sports watch for a sexy and elegant look.

Modern and versatile, canvas slip-on footwear looks excellent with denim, khaki, and chino-style shorts. Guys can get that sharp and clean-cut finish by making sure these textured shorts land right above your knee. Guys with muscular body types can go a little higher, and even cuff the bottoms, for an easy attractive style. If you want to dress up with a bold look, you can always go with chino shorts, a button-down shirt, casual blazer and loafers.

With so many casual men’s shoes to choose from, trendy guys will experiment with contemporary footwear like wool runners, low-profile leather sneakers, slide sandals and chukka boots.

Smart Casual Shoes

If you want to take your outfit to the next level, you can wear smart casual shoes with shorts for a classy and stylish look that will stand out. To pull off a charming style, you’ll need to invest in high-quality smart footwear like loafers, suede Oxfords, dress sneakers and leather boat shoes. Modern gentlemen will also need to shop for shorts that look effortlessly chic and exude style.

For the perfect dapper aesthetic, combine leather sneakers, loafers or Oxford shoes with navy, khaki or white chino shorts, a braided belt, button-down shirt and designer sports watch. Dress up the ensemble with a blazer or take it down a notch with boat shoes and a polo shirt.

Men's Smart Casual Shoes To Wear with Shorts

Classic and trendy, loafers with nubuck uppers and dark leather outsoles work well with dress shorts. Focusing on clean lines and close-to-foot fits will give you that refreshing and fashionable look that stylish guys go for. Versatile and cool, smart casual shoes with shorts are a popular choice for fashion-conscious men.

Dress Shoes

As a flattering and handsome combination, dress shoes with shorts are perfect for outdoor summer events or spring weddings that require you to wear semi-formal attire. Exceptionally sophisticated and chic, you can style your dress shorts with a subtle cuff and then pair your bottoms with dark leather Oxford shoes.

Black shorts and polished black leather shoes look strong and bold, while dark navy dress shorts with brown dress shoes add an elite and dignified tone. Brogues can offer a unique touch and distinct styling to any outfit, especially if you’re pairing this shoe style with tailored designer shorts.

On hot summer days, guys can balance walnut-colored monk strap dress shoes with khaki or chino shorts. For a refined and relaxed approach, top these pieces off with a light and untucked button-down shirt. You can put on a banker-striped button-down shirt to achieve a powerful and sharp look.

A stainless-steel sports watch or leather-strapped dress watch is essential for these stylish outfits. While dress shoes with shorts are always elegant and modern, never forget to check the dress codes for upscale events and venues.

Dress Shoes with Shorts


Sneakers are a wardrobe must-have for fashionable men who want versatile footwear with shorts. Whether you’re going for a hip athleisure style or streetwear chicness, wearing sneakers with shorts can help create a timeless and youthful look. Some guys will want to combine jogging shorts or fitted performance shorts with wool runners for a contemporary gym look that can be appropriate for brunch. Some gentleman may pair low-profile leather designer sneakers with chino shorts and a t-shirt or untucked button-down shirt for a casual style.

For a rugged, masculine and fashionable aesthetic, many guys will wear on-trend shoes with khaki shorts, a polo and an athletic watch. Popular modern brands like Allbirds, Madewell and Atoms offer basic runners in trendy eye-catching colors that look cool and flattering.

Classic brands like Nike and Adidas are tried-and-true and can be styled athletically or fashionably. Guys can pair Dunks or Stan Smiths with a monochrome t-shirt and shorts, then top it off with a colorful windbreaker. Distinct and effortless, you can strike a balance between sporty and urban.

You also can’t go wrong with fitted shorts, a crew neck t-shirt, and low-profile white leather sneakers. Stylish men will seek out limited edition kicks from cool-guy brands like Oliver Cabell, M.Gemi, and Common Projects as well as high-fashion designers like Prada, McQueen and Balenciaga.


Loafers are classic men’s footwear that look mature and masculine, making the different styles perfect to wear with shorts. You can choose casual loafers with shorts and a t-shirt for a comfortable outfit in the summer or create a smart casual to semi-formal look with chino shorts, a button-down shirt and a blazer for nicer occasions.

When piecing together your attire, you can go for elegant and minimalist penny loafers, timeless tassel loafers or luxurious bit-loafers, each providing sleek lines and an attractive ankle presence. Leather bit loafers and dress shorts offer a debonair and sharp style. Iconic and instantly recognizable, Gucci’s horsebit loafers are a worthwhile investment and fashion must-have.

High Top Shoes

If you want a cool look that will stand out, you’ll want to wear high tops with shorts for a bold outfit. High-top sneakers are youthful casual footwear that can create fashionable outfits when styled properly. From khaki cargo shorts with t-shirts to black chino shorts with sweaters, you can make high tops and shorts work to suit your aesthetic.

For starters, you’ll want to invest in classic high-top sneakers from brands like Converse, Vans, Nike and Adidas. Chuck Taylors offer a trendy streetwear style when paired with canvas shorts and a bomber jacket. Fashion a cool retro outfit by wearing your Chucks with denim shorts and a fitted raglan shirt.

High Top Sneakers with Shorts

In the late summer and early fall months, you may try white canvas high-top sneakers with black shorts, long socks and a sweater. You can even dress up your look with fitted chino shorts, suede high-tops and a button-down shirt.

Brands like Beckett Simonon and Koio offer unique leather-crafted hybrid high-tops that are great with smart casual outfits, while luxury designers like Gucci and Prada make fashion footwear for stylish and daring attire. Whether you like canvas, suede or leather high-top styles, you’ll need to experiment with different brands and looks to get the perfect look.

Boat Shoes

Boat shoes are versatile and easy to wear with shorts, providing a smart or casual look depending on your outfit. When piecing together your attire, pick boat shoes that add a sophisticated touch for a weekend power-look or a charming casual touch for an effortlessly chic style.

Guys should consider neutral-colored leather boat shoes with tailored chino shorts and a dress shirt to achieve a classy ensemble. Whether you’re walking around New York City or hanging out at the beach in Los Angeles, try a smart casual summer look that consists of brown leather boat shoes, a white polo shirt and slim-fit chino shorts.

Always refined and masculine, get boat shoes in neutral colors like dark brown, tan, slate, navy or beige for a timeless look. To stand out with bold footwear as your statement piece, invest in bright summer colors.

Boat Shoes To Wear with Shorts


Brogues are a great way to style a classy and timeless aesthetic with shorts, giving guys a dapper and sophisticated outfit that will stand out. Stylish and unique, this formal shoe style will add flair to your look but will require a balance when paired with upscale fitted dress shorts. There are many different types of brogue footwear, including the Derby with open lacing and the Oxford with closed lacing. These dress shoes can also come in different perforations such as full or wingtip, half and quarter.

In the summer, you can wear linen shorts with an understated lightly-woven shirt and a straw trilby hat. For a preppy Ivy League look, you can sport your brogues with seersucker and top off the style with a luxury crew neck t-shirt or a comfortable polo shirt. Brogues are fashionable shoes to wear with shorts and a button-down shirt when you want a smart casual look that will impress.


Sandals are the most casual type of footwear that guys wear with shorts for a cool and comfortable look. Whether you’re at the beach, lake, or a summer pool party, you’ll want to find a good pair of sandals and open-toed shoes to go with your shorts. Some men may choose flip-flops, but we recommend investing in leather sandals from quality brands like Birkenstock and Grenson. The Birkenstock fashion trend works well with utility shorts or light-colored linen shorts, while creative sandals like leather mules and huaraches can offer a unique style.

To maintain a masculine look, get sandals made in dark brown colors like tobacco and java. Flip-flops can be simple, understated and matched to your swim shorts or shirt. For an upscale touch, you can buy a long-lasting pair of fashion flip-flops, like the Olukai leathers or Prada brushed sandal.


Espadrilles and shorts are a natural fit for men who want a cool and casual look. Known to be comfortable and great for the summer, espadrilles are classic rope-soled that add a trendy textured accent to any casual or smart casual outfit. You can get espadrilles with a cotton upper for a relaxed finish or a canvas upper for a simple cool vibe. You can wear espadrilles with shorts in many different ways, making these shoes a wardrobe staple for stylish guys.

Espadrilles with Shorts Men

Guys can go clean-cut and fresh by pairing espadrilles with chino shorts, which can take you from the boardwalk to a lunch date to a music festival. You can round out this outfit with a t-shirt for a flattering basic look, a fitted polo shirt for a nice classy appearance, or a button-down shirt for a smart casual approach. Take your look to the next level by putting on a linen blazer to create a trendy ensemble. As one of the most popular casual men’s shoes, you need a pair of espadrilles in your closet.


Guys can always wear shorts with boots for a sleek and rugged look. While boots and shorts are a natural pairing, there are many different types of boot styles and constructions to choose from. Some guys will choose suede chukka or work boots for a strong masculine aesthetic, while others will go for leather Chelsea or combat boots.

Great for casual outfits, crepe sole desert boots look distinguished with military or khaki shorts, a hunting vest and a tan utility jacket. A field watch like the Hamilton Khaki Field or the Rolex Explorer II is a must-have accessory that will complete this well-balanced outfit.

Cargo shorts and work boots like tan Timberlands paired with a t-shirt make for excellent streetwear that demonstrates flair and fashionable taste. You can also decide to style light suede chukka boots with an equally light-colored pair of shorts and a navy cardigan. Masculine and clean-cut, make sure you keep the top and bottom cardigan buttons undone to achieve this handsome look.

For a bold fashion statement, guys can experiment with dark brown or black suede Chelsea boots. For a smart casual look, try leather Chelsea boots with shorts and a button-up shirt or take it a step further with a short-suit. While this ensemble is risqué for the conservative, fashion-forward men will love pushing boundaries and turning heads everywhere they go.

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