Few things on earth are as sweet as waking up in the morning knowing you’re going to be able to rock shorts and hoodie all day long. The gods don’t often deliver a day just brisk enough, and just warm enough, to make the combination of a worn-in hoodie and shorts the ideal outfit, but when they do, oh boy, is it good. Shorts and hoodie season isn’t just for those of us who love menswear—a similar phenomenon happens for runners like me. I’m calling it “long sleeves and shorts season.” While that doesn’t really have a ring to it, it encompasses more styling options, which is always welcome in the gray area of not-too-hot, not-too-cold temperatures.

When building your long-sleeve-and-shorts running kit, you can choose from dozens of combinations, since the variety is what makes the pairing perfect for any temperature range. I wear shorts until temperatures reach the mid-40s—below that, I’ll reluctantly make the switch to running tights—so living in NYC, I’m in shorts for at least 10 months a year. Once I have my shorts picked out, the fun begins: It’s time to layer up.

To get you started on the journey of wearing shorts in the cold, I compiled some of my favorite pieces that mesh perfectly for those brisk, medium-temperature days when shorts are a must, but keeping your upper body comfortable is a tricky task. Mix and match to your pleasure, and remember that at some point you won’t have so much freedom when it comes to donning your running kit, so get these fits off while you can.

Ciele

Sorino Performance Long Sleeve Shirt

The silk-Merino blend is as luxe as they come, and this shirt from Ciele works on its own or as a base layer. The Montreal-based brand knows something about running in bad weather, so you know it can be trusted when a chill hits the air.

Soar Running

Dual Run Shorts

Another banger from Soar Running are their trail shorts. They have a ton of pockets and integrated elastic bands for keeping EDC and nutrition close at hand, plus the fit is incredible: I’ve never once worried about chafing of any kind in these bad boys, even on runs that go beyond the two hour mark.

Tracksmith

Harrier Long Sleeve

Tracksmith’s soon-to-be-legendary running gear (the brand’s still young!) is great for all seasons. Its long-sleeve Harrier is made of Merino wool, great for its thermo-regulating properties, with a fit that’s tailored to your body without being clingy.

2XU

Aero 9 Tri Shorts

Want to run better and take less time to recover? Compression tights are the way to go, and if you’re sticking to the whole shorts thing, then these nine-inch Aero shorts from 2XU will keep all your muscles compressed so you can perform better and last longer (on your run).

Satisfy Running

CloudMerino Long Tee

Merino is the king of layering. It’s naturally moisture-wicking, temperature-regulating, and anti-stink, so you can wear it all day long in just about any temperatures. You might even be able to sneak two runs in before it starts to get musty. Satisfy’s CloudMerino isn’t cheap, but it’s some of the softest, most comfortable Merino I’ve ever worn.

Satisfy Running

Rippy Dyneema 3″ Trail Shorts

Running shorts are inherently skimpy, but the Rippy trail shorts from Satisfy blend a comfortable base layer with a thicker, more resilient outer layer that provides extra coverage where you need it. Dyneema is one of the strongest materials out there, so, despite their name, you don’t have to worry about these shorts ripping if you encounter unexpected foliage on a trail run.

Bandit Running

Auragrid Mockneck

When temperatures drop a bit more, a grid fleece with a mock neck is the way to go. The neck provides just an extra bit of protection and the material is breathable enough to keep you warm without drenching you in sweat.

District Vision

Ripstop Layered Trail Short

If you haven’t noticed yet, I love 2-in-1 shorts—specifically ones made for trail running. These ones from District Vision pair a comfy half-tight with a ripstop outer layer that provides wind protection and a bit of added warmth around your nether regions, which will be appreciated when you encounter a headwind.

Soar Running

Race Base Layer T-Shirt

This is my go-to base layer for fall and winter running in LA. It’s lightweight, the fit is incredible, and it is easy to pair with other layers. Plus, the white sleeves help when I’m running in the dark.

Janji

M’s 7″ Multi Short 2-in-1

There’s no shortage of pockets with these Janji shorts—a godsend for any runner. From gloves to protect your digits to extra gels, these shorts will make sure you have everything you need whether it’s a warm-up three-mile run or a long-hauler.

How to Stay Warm in Shorts

The optimal upper body combination is a long-sleeved base layer with a short-sleeved tee over the top of it. It’s comfortable, it lets me pair a light long-sleeve layer with something more substantial over the torso if needed, and it makes me feel like I’m in a ’90s music video—which is always a bonus. If it’s extra-cold, I’ll swap out the short-sleeved tee for a long-sleeved one or add a thicker piece over my base layer, like a light fleece, quarter-zip, or sweatshirt. There’s something really fun about getting to flex your personal style on a run, whether that means pairing your favorite band tee with a performance layer or mixing and matching layers in new combinations.

This is also a great time to play with different materials. The cool weather means you won’t sweat much but don’t need to dress like the Michelin Man, so if you love to run in cotton (like I do), toss a long sleeve tee or hoodie on. If you’re going for an all-day adventure or might encounter some changes in the weather, pick out a Merino layer that will keep you cool when the sun comes out and warm when the clouds converge. If a techy, performance base layer is your go-to, throw that on for sweat-wicking, temperature-regulating goodness and throw something different over the top of it. The choices really are endless.

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