Best Shorts For Men And How To Wear In Style

The Best Shorts For Men And How To Wear In Style

The Best Shorts For Men And How To Wear In Style

Athletic, relaxed, or preppy, shorts are the quintessential summer staple that every man needs but most have difficulty finding.  Shorts, given their casual reputation, can read messy and unrefined if done in the wrong fabrics and if the fit is off. Done well, however, and shorts will read polished, boosting your casual wear for summery looks done to absolute perfection. From short shorts to dressier versions, we take you through the best shorts for men to wear this summer. And the best shoes to wear with shorts.

The Dos & Don’ts of Shorts

Shorts are most definitely not the easiest clothing piece to pull off. Whether you are someone who lives in shorts or prefers a pair of jeans, first things first, the fit is everything. Not all men have similar proportions, and the way something sits on someone else may not necessarily complement your body. So try on shorts before you purchase them. Strike an appropriate balance and find shorts that will be fitted, but not entirely constricting. Do not opt for shorts in cheap or ‘board-short’ fabrics for everyday wear – this will read juvenile and will not allude to a mature aesthetic.

When to Wear Shorts


Casual Shorts

Shorts are the answer to relaxed casual looks. Team them with a chambray/linen button-down or a simple t-shirt. A pair of espadrilles or boat shoes will elevate your look and are a more appealing option than the typical thongs most gents tend to wear.

Smart Casual

Smart Casual Shorts

It is important to realize that shorts need to be worn in the right context. We recommend thoroughly considering whether shorts would be ok for the smart casual event you are attending. If so, team chino-Esque shorts with simplistic dress shirts and an appropriate blazer or throw a lightweight sweater over your shoulders. Loafers and sneakers are great shoes for smart-casual events.

Sports Luxe

Sports Luxe

When it comes to perfecting sports luxe, comfortable shorts are integral, but the way they look should take maximum priority. It’s all about the way you adapt sporty clothing for everyday wear, so ensure your shorts are in basic colors for maximum versatility. Team your shorts with other staples, like rich-toned bomber jackets, white trainers, and novel baseball caps for a playful take on the sports luxe trend.

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Different Types of Shorts

There are many short styles on the market, but we’ve selected three of the most versatile styles that should be a part of your everyday wardrobe.

Cropped Shorts / Short Shorts

Cropped Shorts - Short Shorts

The cropped short nods back to yesteryears with their retro vibes and shorter proportions. One of the most versatile short styles; the cropped short offers much in terms of flattering slimmer to medium body types and works terrifically for casual days and nights alike. Versatile tones are great, but don’t be afraid to experiment with a bit of color given this type of short is typically a casual staple piece. Team your short shorts with white trainers, espadrilles, and playful accessories like baseball caps, bright watches, and round sunglasses.

Tailored Shorts


The tailored short is typically reserved for smart-casual looks. With their chino vibes and more inflexible materials, they are great for updating dressy casual looks for the warmer months. While they are stylish, tailored shorts are also great for practicality and will allow your legs to breathe. The main thing you should remember when opting for tailored shorts is to find them in versatile colors like navy, khaki, and beige, which will afford you a great deal of adaptability for your wardrobe.

Baggy Shorts


Your biggest responsibility when it comes to baggy shorts is to ensure that they are well-balanced for your body type. Proportion is key, so ensure you know what works with your body, but more importantly for your height. Experiment with different fits and textures to ensure that the baggy short will be a flattering piece as opposed to reading clownish or dated. Preserve a much shorter length with your baggy shorts.

7 Best Shoes To Wear With Shorts

Thanks to their effortlessly cool style and versatility, shorts can be sported for countless occasions and multiple dress codes. While this adaptability makes shorts an easy choice of clothing, it can also make deciding on accompanying footwear incredibly difficult. Choosing the correct style of shoes is essential to creating a stylish appearance. Luckily, we’re here to help with our guide that shows you the best styles and how to wear them properly.

1. Sneakers

Sneakers with shorts

Looking to experiment with street style in a fashion-forward way? Sneakers are the ultimate choice in footwear for the cool guy. From classic sports brands such as Nike, Converse, and Adidas to the high fashion houses of Prada and Alexander McQueen, designers far and wide are now producing contemporary, must-have sneakers. No matter your sense of style, these casual, comfortable yet fashionable shoes are an essential staple in your wardrobe all year round. Partnered with shorts, sneakers nail an effortlessly cool aesthetic, perfect for the summer months. What’s best is they can be dressed up or down to fit any occasion. For a day-to-day casual look, we recommend pairing your sneakers with a polo or t-shirt. On the other end of the spectrum, a more formal occasion calls for a shirt and chino shorts.

2. Loafers Shoes With Shorts

 Shorts with Loafers

If you don’t already own a pair of loafers, then what are you waiting for? These stylish slip-on shoes are a wardrobe must-have and come in three different styles: penny loafers, tassel, and Gucci. Paired with shorts, loafers make the perfect ensemble for daytime outings. It’s up to you how formal or informal you go, but a pair of chino shorts combined with a shirt, casual blazer, and loafers make a great semi-formal look for the summertime. That being said, loafers are a very versatile shoe. If you’re looking for a casual ensemble, a plain white tee will work just as well. The key to making this look work is choosing the right style in the right color. Of course, this style will only look sharp provided it’s worn sock-free.

3. Brogue Shoes With Shorts

Shorts with Brogues

For a classic look, brogue shoes are a timeless item in men’s fashion. Not only are they neat and stylish, but they can also add a unique touch to any outfit thanks to their distinct perforations. Brogues typically come in two styles: the Derby with open lacing and the Oxford shoes with enclosed lacing. They are further categorized by the different perforations they feature. Designs include the full brogue (wingtip), half brogue, and quarter brogue. When styling an outfit, it’s important to remember that a smart shoe must be matched with a pair of equally smart shorts. Coupling brogues with tailored shorts creates a look that’s perfect for a smart-casual setting. The key to making them look great is to balance them with a classic colored shirt. Just remember to ditch the socks and grab a pair of sunglasses.

4. Sandals and Flip Flops

shorts with sandals

Spending the day on the beach or by the pool? You’ll need a shoe that is both comfortable and breathable. Sandals are a great choice in footwear for the summer months. Being such an affordable and simple shoe, it’s no surprise why they’ve become so popular in recent years. There are now so many styles to choose from, and when paired with shorts during the warmer weather, they make a great match. For this look, team a pair of pool or denim shorts with a plain tee and practical sandals. Just make sure your feet are properly groomed before slipping on these shoes.

5. Boat Shoes With Shoes

Shorts with Boat Shoes

When boat shoes are worn the right way, they can be incredibly stylish and can bring some maturity to an outfit. Boat shoes strike a comfortable balance between smart and casual, making them easy to dress up or down. When it comes to more formal events, pair them with chino shorts for an effortlessly refined look. Opt for a good fit, and match them with a tailored shirt for balance. It’s best to choose boat shoes in neutral colors such as navy, tan, or beige.

6. Espadrilles Shoes With Shorts

Espadrilles With Shorts

For a casual yet trendy style, espadrilles are a great option. These shoes are one of the comfiest summer shoes on the market. When it comes to styling these shoes, there are a few items of clothing that will help you achieve a casual appearance. As versatile as they are stylish, chino shorts are one of those items you can sport for multiple occasions. Pair them with your espadrilles, a shirt, and a blazer for a polished look. Or for something a little more casual, a simple polo teamed with denim shorts will create the perfect weekend ensemble.

7. Desert Boots With Shorts


While shorts are thought of as the cool, casual essential in any wardrobe, the addition of some desert boots can instantly change their appearance. The classic footwear style is a staple for any closet and lends a unique aesthetic to any ensemble. Ideal for casual outfits yet easily dressed up for more formal occasions, these shoes are versatile and fashionable. Pair desert boots with a tailored shirt and chino shorts for a rugged yet chic appearance. Boots and shorts may seem like an odd combo, but coupled with the right clothing, it can make for an ultra-stylish ensemble!

Best Shorts For Men

Shorts are a great way to enjoy the heat of summer while looking stylish, without having to die in your warm, itchy, smelly jeans.

The Best Shorts can easily be dressed up or down, depending on the occasion – they’re the perfect staple to a summer wardrobe.

Choose one made of the finest natural material such as linen, cotton, and chambray to allow your skin to breathe. Excessive pockets that come with varieties such as cargo shorts are a no-go, instead, choose something that is minimal yet practical.