Here are the best shoes to go when you are wearing shorts but wanted to still look cool and classy.

Dressing up classy and smartly boosts confidence level. You feel better and more confident to face the day when you look good. How you look and feel will affect your disposition, so it is encouraging to dress up classy.  On casual days, you feel like wearing shorts; hiding those toes is critical to looking classy. Save those espadrilles and sandals on the beach because if you opt to look smarter and classy in shorts, you must pair them with shoes. 

Here are the best shoes to wear with shorts to look classy.

Casual sneakers

Sneakers are the most versatile shoes in various styles, from minimal to Jordan, and are made in leather or canvas that are good to wear in warm weather. They can be dressed up or down to fit any occasion and style. 

For a classy look with the right balance of casual and comfort, opt for toned-down and minimal styles. The neutral colours, such as off-white and black, match almost any shorts and style. 

5 Best Shoes To Wear With Shorts To Look Classy


A pair of loafers is a must-have for men who want to look smart and classy. Loafers come in three styles: the penny, tassel, and Gucci. These are mostly lightweight and classic slip-on styles with flat heels. 

Being another versatile and best shoes, loafers are great for that semi-formal look while enjoying more comfortable footwear. For a classy style, opt for a toned-down style, stick to browns and blacks, and ensure the shorts’ style is equally smart-looking. Lastly, when pairing it with shorts, wear it sock-free. 


Brogues are dressier shoes for men, but their versatility goes from a rugged look to a slim and more elegant look.

Opt for brogues and chino shorts to achieve a smart and classy look. Do not underestimate the appeal of well-polished brogue shoes for a killer combo in warmer weather. 

For Robert Johnston of GQ Magazine, “As for the brogue/short/polo combo, it will look great. Two things, however: leave the polo untucked and don’t wear socks.”

5 Best Shoes To Wear With Shorts To Look Classy

See: How to Take Care of Your Leather Shoes

Boat Shoes

Unarguably, boat shoes are the most iconic style of casual shoes and the best option when you are going to be around water. The soft rubber sole and the leather section make it comfortable to wear while conveying a timeless, cool, effortlessly stylish, refined look.

Boat shoes in neutral colours best style with chino and linen above-the-knee shorts and tailored shirts for balance. Darker tones of these best shoes are perfect for business-casual aesthetics, while lighter colours make for semi-formal styles.

5 Best Shoes To Wear With Shorts To Look Classy

See: How to Wear Boat Shoes for Different Occasions

Desert Boots

Desert boots make you look dapper in a flash, whether summer or colder. When you want to take a break with your boat shoes and leather brogues, desert boots are the following best style to wear with shoes. 

For a casual yet smart look, pair the brown, beige and black desert boots with the chino shorts and smart-look unbuttoned shirt. You can also wear it in a relaxed suit. 

Pro tip: Opt for a sock-free look for a sleek and classy style when wearing shoes in shorts. However, you can also wear socks but make sure that it is invisible. 

In classy style, shorts and shoes are perfect to don, especially in warmer weather or simply if you want to forgo using pants. However, not all footwear is applicable because some will make you look sloppy. That is why, here are the best shoes that you can perfectly pair when you are wearing shorts and achieve the right balance of smarter appeal and comfort.