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Men’s Guide to Styling With Shorts

Styling with shorts - A man wearing denim shorts while standing in front of a bike.

When the hot summer months start, it’s time for every man to switch from trousers to shorts. However, for most guys, styling with shorts is a tricky fashion choice as they simply can’t tell what to wear them with. This is why most men prefer to wear shorts only indoors, as they are unsure of how to style up when stepping out.

This post aims to make things less confusing by suggesting some fashionable styling tips you can try out. Dig in!

What to Wear Shorts With

Shorts come in different designs, colors, shapes, and sizes. While some are smart-casual and are okay to wear to the office, others are only ideal for taking a stroll at the beach. When styling with shorts, the rule of thumb is always to wear a shirt, socks, shoes, or accessories that match the vibe of your shorts. 


Shorts are casual, and so should be the shirts they are paired with. For your fabric shorts, wear them with a polo, v-neck, or short-sleeve, button-down shirt. Avoid long-sleeved, button-fronted, collared shirts as much as possible, as they are too much of a stylistic mix, even with the sleeves rolled up. 

T-shirts are easy to match with shorts as they go together so well, creating a simple yet effective style. If you want to add some sophistication, try layering up with a button-up shirt over the T-shirt. 

A Two-Piece Set

A two-piece short suit, or a casual set, is a wardrobe staple. These matching outfits are ideal for dinner parties or a night out at the club. However, note that most two-piece sets are bold and in your face. Therefore, if you are ready to embrace the spotlight and flaunt your wild side, this trend is perfect for you.  


When styling with shorts, the most popular casual shoes include slip-on and laced Vans. Some simple, low-top canvas sneakers are also a comfortable choice for most men. You could also wear your nice pair of shorts with slip-on loafers or boaters. Sandals are generally the most casual option: okay for a casual stroll at the beach but highly inappropriate for a graduation party. 


The general rule of thumb is to avoid long socks when styling with shorts. This is why it’s best to skip any shoes requiring long socks or looking awkward without socks.

Ankle socks work well with most shoes worn with shorts. They can help keep you comfortable if you aren’t used to wearing shoes without socks. If you want to wear sandals, avoid wearing socks underneath unless you are targeting an extremely custom look.  


You can elevate your look using the following accessories:

  • Watches. A watch is a critical element of a grown man’s summer style. Choose one that’s simple, durable, and functional.
  • A pair of sunglasses. Men’s sunglasses are also some of the most popular summertime accessories. To complement your summer look, wear sunglasses that perfectly fit your face.
  • Hats. You should also step out of your comfort zone and try wearing a hat to add to your sophistication and culture. A hat is a statement piece and the perfect topper for any look.

How to Wear Shorts to Every Occasion

Shorts are versatile and will keep you cool and comfortable this summer, regardless of where you are headed. Consider trying out some of the outfits below:

  1. Stretch cotton shirts are a summer staple. They are ideal for any occasion, and their breathability and stretch fabrication ensure you remain cool and comfortable throughout the day. Try pairing them with a linen shirt and boat shoes to achieve the ultimate smart-casual vibes.
  2. When it’s time to hit the bar, you can wear your khaki shorts with a burgundy print shirt. This look goes well with sleek, minimalistic leather, traditional canvas sneakers.
  3. Denim shorts are perfect for casual under the sun, whether at the beach, bar, or BBQ. The most obvious garment to wear them with is a T-shirt, but you could switch things up with a nice linen shirt. Complete the look with a slip-on shoe or a laced sneaker, and you are ready for a fun summer evening.
  4. If you want to keep things simple and effortlessly chilled, you can never go wrong with a pair of linen shorts. This breathable material is perfect for a smart-casual event or an evening stroll. Pair these versatile shorts with a light shirt or T-shirt and some sandals. 

As evident, shorts do not always have to be plain and boring. At Family Britches, we strive to create timeless and outstanding looks for the modern man. Discover custom-tailored, high-fashion clothing with us for the perfect summer wardrobe.

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