Perfect Shoes to Rock with Shorts: A Style Guide for Men & Women 

April 25, 2025

When the temperatures rise, there’s one staple style that always comes back in rotation - shorts. From tailored city shorts to breezy resort wear, this warm-weather essential keeps things cool without compromising on style. Throughout history, shorts have been a staple not only for fashion but also for functionality and comfort. But here’s the real challenge: finding the perfect shoes to wear with shorts. 

The right footwear can either pull the whole look together or completely throw it off. Even the most well-designed shorts that you can pick won’t make you look good if you don’t pair them with the right pair of footwear. Whether you're planning a Sunday brunch, a stroll by the beach, or even a smart-casual dinner, your shoe game matters when it comes to shorts. Especially because they’re on full display.  

To help you pick the right shoes to pair with shorts, we’ve created a guide. This is your ultimate guide to shoes that go with shorts - designed for both men and women, with handpicked styles that bring together premium design, comfort, and unmatched style. So without further ado, read on to find out how to pair the right shoe with shorts in your wardrobe. 

Best Casual Shoes to Wear with Shorts

Let’s start with off-duty dressing, which is where you’re most likely to wear shorts. When you’re going for laid-back comfort with polish, here are some winning footwear picks that you can choose from. 

Slip-On Sneakers

Classic, fuss-free, and forever in style—slip-ons are the ultimate go-to when you want a put-together casual look without trying too hard. Pair them with denim shorts and a linen shirt or a cropped tee for a look that’s effortlessly cool. Go for no-show socks if you want to keep the look clean and minimal, or even pick statement socks if that’s your style. 

Perfect for: 

• Quick local coffee runs 

• Airport travel days 

• Weekend errands in the area 

Ladies, if you’re updating your wardrobe of shoes that can be paired with shorts, don’t miss Metro’s edit of women's sneakers. 

Minimalist Loafers

Loafers aren’t just for formal wear—they’re just as at home in a smart-casual setup with tailored shorts and polos or printed shirts. They’re one of the best pairings with shorts when your top wear is a semi-casual style like a half-sleeved t-shirt or a polo shirt. 

Perfect for: 

• Brunches with friends, where you’re looking to strike a casual premium look 

• Sundowners, where the style quotient matters 

• Casual Fridays at work (if your dress code allows) 

Men, it is time to elevate your shorts look with structured loafers for men. 

Dress Shoes That Go Well with Shorts

Think shorts can’t look sophisticated? Think again. The trick is in styling them with the right structured, dressier footwear. Here’s how you can pick the right dress shoes to go with your shorts look. 

Pointed Flats & Mules (for Women)

Pairing shorts with pointed-toe flats or elegant mules gives your look instant polish. Perfect for pleated or paperbag shorts paired with a blouse or blazer. Make sure to check out your look once before finalising it, as the colours and patterns on each piece can affect the overall synergy of the look. 

Penny Loafers & Driving Shoes (for Men)

Opt for leather or suede styles with dress shorts and a button-down shirt. Avoid socks for a clean, European-inspired finish. This is a very popular look for vacations and Euro-trips. Beach destinations especially see a lot of this style. 

Perfect for: 

• Date nights where you’re looking to make a good impression 

• Upscale lunches where the style quotient matters 

• Creative professional settings where you want to come across as fashionable  

If you're going for shoes to wear with dress shorts, lean toward materials like leather or velvet and silhouettes that feel more refined and elevate the overall elegance of your look. 

Sneakers and Trainers: The Perfect Pairing for Shorts

Let’s be honest - sneakers are the universal shoe solution. And when it comes to shoes to wear with shorts, they’re a go-to for a reason. They can be mixed and matched with almost any type of shorts, and that’s why they’re so popular. Here are the types of sneakers that you can pick from to make your shorts look pop. 

1. Chunky Trainers

Great for street-style looks with biker shorts, tennis skirts, or even oversized blazers. These add volume and impact to your look that goes perfectly with street style. 

2. Classic Low-Tops

Whether canvas or leather, low-tops work beautifully with chino shorts or denim cut-offs. Add a plain tee or a polo for a modern, clean aesthetic. These land the old-money aesthetic. 

3. White Sneakers

The MVP of your wardrobe. White sneakers go with literally everything. Pair them with printed shorts, monochrome looks, or co-ords. White or any other neutral colour is always the best to pair with a wide range of options. 

These styles work for both men and women—make sure to invest in a quality pair that offers both comfort and statement style. 

Sandals and Heels: Stylish Summer Footwear for Shorts

When it comes to summer shoes that go with shorts, few pairings beat the effortless combo of sandals and shorts. Sandals are the OG pairing with shorts that you can never go wrong with. 

Sandals for Men & Women

Leather sandals or strappy flats instantly give your look that Mediterranean vacay energy. Whether you’re wearing linen shorts or a flowy playsuit, sandals bring the breezy vibe. Pick ones that have an easy closure so that you can take them off easily when you’re headed to the beach or just lounging. 

Explore Metro’s newest men’s sandals for timeless summer elegance. 

Heeled Sandals or Wedges (for Women)

Want to take things up a notch? Wedges or block-heeled sandals with shorts are perfect for summer evenings, brunches, or rooftop events. These depend on the cut of the shorts that you’re picking. 

Best Shoes to Wear with Shorts for Different Occasions

Let’s match your footwear to your calendar, shall we? Here’s a handy table that will help you get every choice right when it comes to choosing footwear to go with your shorts. 

Occasion	Recommended Shoes
Beach vacation	Strappy sandals, espadrilles, flip-flops
Brunch date	Loafers, mules, platform sandals
Travel / airport	Slip-on sneakers, trainers
Casual office days	Dress loafers, minimalist sneakers
Dinner parties	Heeled sandals (women), leather loafers (men)
Concerts / Events	Chunky sneakers, low-top trainers

Bonus Tip: When in doubt, build your look around your footwear. A standout pair can dictate the vibe of your whole outfit. 

Conclusion

Shorts are no longer reserved just for casual weekends—they’ve become a canvas for creative, refined, and fashion-forward dressing. And the secret to making them look premium? The shoes. 

From sleek loafers to sporty sneakers and elegant sandals, there are endless shoes to wear with shorts for every mood, moment, and personality.

At Metro, we design footwear that’s as versatile as your lifestyle. Whether you’re dressing for city strolls, getaway days, or sunlit soirées, our curated collection—spanning sandals for men, women's sneakers, and loafers for men—ensures your shorts game stays strong and stylish.