Men’s Shorts in Winter & Fall: How Cold Should You Go?

Asking how long you can wear men’s shorts into cold weather is a bit like asking how hot you like your soup. Everyone’s preferences are different. But if you’re curious about the fashion rules pertaining to men’s shorts in winter and fall, then there are a few things you should know before it comes time to switch to pants.

To Shorts or Not to Shorts, That is the Question

What will you prefer? It depends on your own situation:

  • In New England, you’ll see most shorts disappear around October, November ath the latest. Dealing with a harsh New England winter means bringing out the warm clothes, and try as they might, New Englanders can only hold out for so long. With a mild winter in South Carolina, for example, you’ll likely see at least a few pairs of men’s shorts year round, even into the colder months.
  • If you like to ride your bicycle a lot, then cool air moving quickly can require some added warmth. If you simply need to lounge around the house, however, shorts are perfectly comfortable even as the weather gets cool outside.
  • Some people are more comfortable in pants than shorts, and vice versa. Some can’t wait for fall to arrive and switch to Stretch Corduroy. Others simply lengthen the cut of their shorts to 9-Inch Men’s shorts and keep the summer alive.
  • Sometimes, it’s simply a matter of personal style. You can add some warmth to your outfit by switching to long sleeves for a “preppy” look in the fall, or you can switch to pants and start getting ready for winter. It’s completely up to you.

To determine how long you’ll keep wearing shorts as part of your routine this year, ask yourself what’s most important to you.

Men’s Shorts in Winter: How to Wear Your Shorts Longer

If you decided that your personal preference is to wear shorts as long as possible, there are a few ways you can keep warm without getting weird looks.

  • Add a sweatshirt. You’d be surprised at just how much total-body warmth you can get simply by adding a warm sweatshirt and keeping the shorts. Throw a sweatshirt over these Sunny Stretch Twill Flat Front shorts, and you’ll be able to squeeze more life out of what you thought was simply a summer purchase.
  • Add a rugby shirt. The “New England preppy” look often includes long sleeves on top of shorts as the weather starts to cool.
  • Switch out the sandals and hike up the socks. No matter what you try to do, at some point, it will get too cool for sandals. Although no-show socks are all the rage these days, don’t be afraid to wear quarter socks with shorts. It would look strange in summer, true, but when the mercury drops, no one will wonder why you’re wearing them.

Typically, cold weather climates will only allow a sane person to keep wearing shorts until October or November. When winter hits in earnest, you may want to switch out the shorts for thick pants like Vintage’s Stretch Corduroy. With the lessons you’ve learned here, though, you should have no problem wearing your shorts throughout the year.