The cold weather shorts rule

Shorts above 55. Joggers below.

Under 55Switch to joggers and a hoodie.
55 to 64Shorts, but the top half carries it.
65 and upShorts and a polo. No debate.
ColdCoolShorts weather

Yes, men can wear shorts in winter, down to about 55 degrees. Above that line the shorts work if the top half is warm. Below it, switch to joggers, because the knees give out before the style does.

55The 55 degree rule

The rule is simple. At 65 and up, wear shorts and a polo. From 55 to 64, wear shorts with a crewneck or a hoodie. Under 55, wear joggers. Wind drops the number by five, so a 58 degree windy morning is a joggers morning.

Phoenix highs sit near 67 in December and January, so Arizona men get a lot of shorts days in winter. The catch is the morning. A Scottsdale 6 AM tee time starts in the 40s, and shorts at that hour are a mistake you make once.

Temperature Bottom Top
65 and up Drew Short 5 or 7 inch Tom Polo
55 to 64 Drew Short 7 inch Alec Crew or Hayden Hoodie
Under 55 Alec Jogger Hayden Hoodie

65+What to wear at each temperature

65 and up

Shorts and a polo. Pick the five inch if it is 70 or hotter, the seven inch if it is not.

55 to 64

Seven inch shorts and a warm top. This is the zone people get wrong.

Under 55

Joggers and a hoodie. Do not fight it. You will look better and feel better.

Drew Short 7 inch in Fern, athletic shorts for men | PILLAR
Drew Short 7 inch FernThe all season short. Seven inches covers more knee when the air cools.$55
Tom Polo in Grey, performance polo for men | PILLAR
Tom Polo GreyA polo with shorts reads as a choice, not a mistake.$40
Alec Crew, crewneck for men on cool mornings | PILLAR
Alec CrewThe warm top that makes shorts work at 58 degrees.$85

7inWhy the seven inch wins in winter

A seven inch short covers about two more inches of thigh than a five inch short. In cool air that is the difference between comfortable and cold. Keep the five inch for the warm half of the day. The 5 inch versus 7 inch breakdown walks through the exact numbers, and the inseam guide covers golf, pickleball and the gym.

Drew Short 5 inch in Black, athletic shorts for men in heat | PILLAR
Drew Short 5 inch BlackFive inches is for 70 degrees and up. Save it for the warm half of the day.$55

TOPThe top half does the work

Warm top, light bottom. A crewneck is the cleanest answer because it hides the shorts line and holds heat at the core. A hoodie does the same with more weight. Read crewneck versus hoodie if you cannot decide, and what to wear under a quarter zip for the layer between.

Keep the colors apart. Navy top, sand or fern short. If both pieces are the same dark, the outfit reads as pajamas. For longer weather swings, what to wear in 50 degree weather has the full list.

<55When it drops, swap the bottom

Under 55 the move is not a warmer top. It is different pants. A jogger gives you the same comfort as a short with none of the cold. Read joggers versus sweatpants before you buy, then pair the Alec Jogger with a Hayden Hoodie. If a polo is underneath, fold the collar out.

Hayden Hoodie in Beige, hoodie for men | PILLAR
Hayden Hoodie BeigeBelow 55, the hoodie goes on and the shorts come off.$98
Alec Jogger in Black, joggers for men | PILLAR
Alec Jogger BlackThe swap. When it drops under 55, change the bottom half.$89

BUYTwo kits, one click

Both kits clear free shipping over $75. Choose your size and go straight to checkout.

Warm day kit, $95

Drew Short 7 inch in Fern and the Tom Polo in Grey.

Buy the kit in SBuy the kit in MBuy the kit in L

Cool morning kit, $140

Drew Short 7 inch in Fern and the Alec Crew.

Buy the kit in SBuy the kit in MBuy the kit in L

Frequently Asked Questions

Can men wear shorts in winter?

Yes, down to about 55 degrees. Above that, shorts work if the top half is warm, like a crewneck or a hoodie. Below 55, joggers are the better call.

What temperature is too cold for shorts?

Under 55 degrees is too cold for most men, and under 45 is cold enough that you will notice it in your knees within minutes. Wind and shade matter as much as the number on your phone.

Can you wear shorts in 50 degree weather?

You can if you are moving, like a round of golf, a run or a pickleball game. If you are standing around or sitting, put on joggers. Movement is what makes 50 tolerable.

What shorts length works best in cool weather?

Seven inches. It covers more of the knee than a five inch short, so the cold hits less skin. Save the five inch for 70 degrees and up.

What should I wear on top with shorts when it is cool?

A crewneck or a quarter zip, in a color that does not match your shorts. Warm top, light bottom is the whole trick, and it is why a hoodie plus shorts looks intentional.

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