Shorts can be one of the trickier menswear garments to navigate. Guys often feel unsure of the proper fit, or even self-conscious about the suitability of shorts in a given environment.

That said, short styling can be broken down into a few easy-to-remember rules and recommendations. The first, and most important, is fit.

Inseam

Inseam, or the length of your shorts, is the most important aspect of both the fit and style of your shorts. Generally speaking, inseams run from five inches in length (the shortest length, typically reserved for guys who want to show a bit more thigh) and eleven inches (reaching to or slightly below the knee). 

“Standard” short inseams usually fall between seven and nine inches, with nine being considered an universally acceptable length for most guys. Falling roughly an inch to two inches above the knee, the nine inch inseam is the length most often employed for off-the-rack short sizing. 

Finding the inseam that works best for you will mean deciding how much thigh you’re comfortable showing while simultaneously respecting your proportions; for example, if you’re taller with longer legs, you may want to default to a nine inch inseam rather than the shorter five or seven inch inseams. Men of average height with more muscular legs will feel more comfortable with a five or seven inch inseam. 

As a general rule, shorts longer than ten inches run the risk of appearing ill-fitting and unflattering to your legs and body. Before you throw any of your existing shorts away, though, it’s worth noting that many shorts with longer inseams can be cuffed or rolled to achieve a more stylish and flattering length.

Styling

Shorts are, as a rule, a casual garment. But that doesn’t mean they can’t be dressed up for more formal occasions. 

A tucked-in dress shirt will work best with a pair of shorts when the midsection is properly tapered (not bagging or blousing out around the waist). A well-matched belt will also be crucial to pulling everything together, especially when wearing a tucked shirt. 

Untucked dress shirts look best when their length falls just shy of the bottom of the crotch of your shorts. The longer your shirt is, the shorter your shorts will appear - so you’ll want to pay careful attention to the balance between shirt and short lengths. 

Likewise, casual tees, henleys and polos are best worn untucked with shorts. You’ll want these more casual shirts to fall two to three inches below the waist or beltline. 

Shoes

When choosing shoes for an outfit with shorts, think low: lower ankle-height shoes or sneakers are great, slip-on shoes or loafers even better. 

In the age-old argument of whether or not to wear socks with your shorts, personal choice will weigh heavily. For most ensembles, though, no socks will almost always be preferable; this is especially true of dressier outfits.

In the rare instances where socks do work with shorts, they’re typically worn with athletic or skateboarding shoes (think: low-cut classic Vans sneakers). This can be treacherous stylistic territory, though, so proceed with caution. 

For guys who require socks for pragmatic or hygienic purposes, no-show socks are a wonderful way to keep your bare feet covered while avoiding the pitfalls of ankle-socks-with-shorts. Luckily they’ve become readily available online and in stores in recent years.