How to Style Mens Shorts

Looking stylish in summer is a bit trickier than it is in other seasons. In cold weather you can wear multiple layers, have your choice of every fabric, and have more styles to choose from. Warm weather necessitates wearing only those layers and fabrics that breathe or wick moisture. You need to make each piece you put on count – in the best way.

Wearing shorts, while great for your comfort, complicates creating a stylish look even further. We’ve discussed how important it is to wear properly fitting shorts and the best short lengths to wear in our Shorter Men’s Guide to Wearing Shorts, and have an overview of Peter Manning short options in It’s Shorts Season, yet putting together stylish shorts outfits still may cause you angst.

Wearing shorts means that there’s a big blank space between your shorts hem and your feet. Your shoes and socks, or lack thereof, becomes a much bigger piece of your style story. When you have so little fabric and so few pieces involved, it’s important that every detail harmonizes because it becomes glaringly obvious if something is out of whack.

It’s been proven that women notice what shoes you’re wearing before they notice your shorts or shirt. Yet you want your shirt and your face to be the focus of your outfit. It becomes much more important to wear shoes that complete, rather than compete, with the look you’re trying to achieve. Your shoes aren’t partially hidden by your pants.

Every element of your outfit must balance in tone and heft. You want to keep a consistent level of dressiness between your shirt, shorts, and shoes. Similarly, you want to keep a consistent weight or look between all the elements. For instance, a large, bulky sweater or jacket will throw off any type of short you choose (chino, denim, tech, sport, or swimming). Similarly, wearing bulky, puffy, bright multi-colored high-top sneakers will diminish whatever else you’re wearing. The first, and probably only, thing that will be seen is your bulky shoes at the bottom of bare legs. If either the bulky sweater or shoes were part of a winter look that included a couple layers on top, full-length pants, a jacket, etc. the bulky item would be more in proportion with the rest of the outfit.

Let’s take a look at what it takes to coordinate an entire outfit for casual and dressy occasions with each piece making sense aesthetically while still being comfortable. It’s possible to do this with foundational garments that you may already have in your closet. It’s merely a matter of making the best use of what you have and adding the touches that will elevate boring or awkward to fashionable and comfortable.

Shoes to be worn with shorts

It’s worth giving a short summary of all the different types of shoes that you may want to wear with shorts before discussing which complement different types of outfits. Many, you are familiar with and may already have in your closet; a few you may never have considered. We’ll discuss them from the most casual and minimal to the dressiest.

• Flip-flops - Many people (style gurus) believe that flip flops and even slides only belong at the beach or pool, but the general population wears them out casually. If you want to elevate your look you can invest in a nice pair of leather flip flops or sandals rather than relying on plastic choices. You can find many intriguing casual options at shops such as OluKai® for flip flops, slides, sandals, and summer loafers. 

• Slides are often made of a plastic material like the ones worn by Jesse Eisenberg in “The Social Network”. They shouldn’t be worn with socks! The most familiar leather/suede slides would be those made by Birkenstock. (They also make sandals and styles that come in canvas rather than the familiar nubuck and leather.)

• Sandals come in a variety of materials and styles. Just remember not to wear them with socks!
• Espadrilles are from the Basque region of Spain and are made from canvas with a braided jute rope sole. Today you can find versions with crepe or other sole materials. The canvas uppers may need some breaking-in, and they aren’t designed for long distance walking; but they can go from very casual to dressier and give off a more sophisticated, European vibe. Rivieras carries a large selection of interesting styles and subtle patterns.   

• Huaraches are originally from Pre-Columbian Mexico and are usually made with braided leather and a thin sole, often made today from recycled rubber tires. They bridge the shoe and sandal. Their open spaces make them breathable, yet they provide more coverage than flip-flops or sandals for those who don’t want to flaunt their toes.
• Sneakers (canvas, leather, other fabrications) are a huge category. You can’t go wrong with sleek, minimalistic leather, traditional canvas (low or high-top) or suede versions. Unless you plan on a lot of walking, running trainers are better paired with very casual and athletic wear. There are a number of newer shoe companies like Allbirds that offer shoes in woven fabrics from eucalyptus or even wool in sneaker-like styles. These are a step up from other sneakers yet offer the cushioning and comfort of a higher tech trainer.
• Boat Shoes were first introduced by Sperry in 1935 to provide traction on slippery surfaces - like boats. Originally all brown, today you can find them in many colors of leather or suede, including multi-colored. Boat shoes are meant to be worn without socks, allow for ventilation, and are appropriate for all but the dressiest outfits. (Sperry also makes sneakers, sandals, and loafers.)
• Driving Shoes are similar to boat shoes, but they have rubber nubs on the toe pad and heal. These are a bit heavier than boat shoes and a bit dressier. They can be worn with socks when you’re wearing pants. With shorts, wear no-show socks, if any. 

• Loafers, brogues, or Derby shoes are usually only worn with dressy shorts outfits. Suede versions are more visually appropriate, especially when they are done in lighter colors. Remember to keep them minimalist and without heavy, dark soles. 

The final consideration is socks – should you wear them and what type of socks should you wear. The absolute biggest NO for socks is not to wear them with sandals or slides. Generally, if you want to wear socks for comfort, wear no show or ankle socks so they won’t be seen. The only possible exception is if you’re wearing high-top canvas sneakers.

Styling beach & athletic wear 

Starting with the most casual of summer wear - things you would wear to the beach, running errands on the weekend, or hanging around the house by yourself or with friends - you may prefer to wear jersey or tech fabric shorts. You’ll find that level of comfort in our Peter Manning Workout Shorts or Tech Shorts.

Our Tech shorts have a 7” inseam and mimic the style and silhouette of Chino shorts so they bridge the gap between super casual and casual. They are made of quick dry nylon and have UV protection so they are also perfect for a day out in the sun (or water).

Our Workout shorts have a 5” inseam, drawstring waist, quick dry, moisture wicking technology and UV protection of UPF 50. The polyester/elastane fabric is stretchy and it has a built-in lining. For workouts, you may want to pair your shorts with a tech fabric shirt for high wick-ability.

Keep in mind that shorter shorts usually give off a more casual vibe than a longer short (still kept 2-4” above the knee).

Both shorts look great with t-shirts (crew or v-neck), polos, or henley’s. Looking down to your feet, you have the option of wearing sneakers (either slim looking minimalistic leathers or canvas, or if you are planning on being active rather than casual relaxation, trainers), sandals, slides, or even flip flops.

Boat shoes are another appropriate water day shoe.There are a couple other types of shoes that can also be worn with casual outfits. All of these can and should be worn without socks.

Styling for a casual day out

For a casual day out – shopping or a meal – tech shorts and especially chinos are appropriate shorts. Add any of the shirts mentioned above or choose a Short Sleever in madras, linen, or seersucker button-up shirt. All of these can be worn untucked. (Remember that Peter Manning shirts are proportionally sized so your untucked shirt will be the proper length as will the sleeve hems.) Most shoes will be appropriate; however, you might want to stay away from clunky trainers, flip-flops, and any shoe that is either too dressy or casual for the shirt you choose.

Another great look for chino shorts is to pair them with a Peter Manning Casual Shirt (long sleeved shirt) and roll the sleeves up to your elbows. Peter Manning offers poplin versions in stripes and gingham checks as well as solids. These shirts are lightweight enough for summer wear – especially for evening events and paired with loafers or espadrilles to present a sophisticated look.  

Shorts with rolled long-sleeve shirts were actually first worn in WWII as the uniform of the Desert Rats, Afrikakorps, and Free French Corp. Prior to that time, shorts were relegated to children who tended to rip the knees of their pants playing. After the war, shorts were embraced by men for the cool comfort they provided.

Business casual & dressier affairs

There are some instances where shorts, however dressed up, aren’t appropriate. Some companies have dress codes that prohibit them (often banks, law offices, or corporate headquarters). If you are unsure whether shorts are allowed, veer on the side of caution and skip the shorts.

If you’re wearing shorts to a dressier event, stick with chinos or linen shorts with cotton, linen or seersucker Short-Sleeved Shirts, or a long-sleeved shirt. Untucked shirts give off a more casual vibe than tucking it in and adding a belt. Of course, you can also choose a light-weight sweater vest or sweater to add over the shirt. Another option is to add an Unstructured Linen or Seersucker Jacket. The most appropriate shoes would be leather/suede loafers or slip-ons, brogues, or driving shoes. You’ll want to move away from sandals, sneakers, flip flops, etc.

Final Thoughts…

As always, the fit of your clothing will make or break your look. Even dressed casually, your clothing needs to fit properly. Putting together a great looking shorts outfit can be trickier because each part of the outfit is more noticeable – especially your shoes. You need to make sure that all the pieces of the outfit work together harmoniously. Each item should evoke the same level of casual-to-dressy mood.