The 10 Best Transitional Clothing Pieces for Working Outside—No Matter the Season

Updated: Nov. 17, 2023

When the temperatures start changing, be ready for anything with these transitional clothing picks.

Sponsored By: Dickies
A portion of this piece was created in partnership with Dickies, an iconic brand that's been making workwear and apparel since 1922.

The 10 Best Transitional Clothing Pieces For Working Outside—no Matter The SeasonVIA MERCHANT

Transitional clothing is a must for anyone who spends time outdoors and needs workwear that holds up. Whether you’re working on an outdoor project or heading to a professional jobsite, you’ll want to be ready for whatever Mother Nature throws at you.

We found must-have transitional clothing picks for cold weather, hot weather and everything in between. That means you’ll stay comfortable and dry on those in-between days when you just don’t know what to wear. (You can thank us later.)

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Convertible Pants
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Convertible Pants

Available for both men and women, The North Face has made convertible pants for years, which have been a must-have transitional clothing staple. This pair is extremely versatile and made of a soft, sustainably conscious fabric. They have zip-off legs, so you can leave them long for cooler temperatures in the morning or evening, then remove the bottoms to make them shorts when the temperatures are at their highest. Plus, they offer some ultraviolet (UV) protection and resist odors.

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Hooded Quilt Jacket
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Hooded Quilted Jacket

One of the easiest ways to transition between hot and cold (and cold and hot) weather? A quilted jacket from Dickies. The faux fleece interior and diamond quilted lining provides warmth during the cooler months, but it’s not a bad idea to keep this jacket nearby for unexpected temperature drops all year. The hood comes in handy for rain and four pockets ramp up the practical factor. The Big & Tall sizes mean everyone can rock this piece comfortably. Speaking of coming in handy for rain, these are our picks for the best rain gear.

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Dickies

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Women's Water Resistant Pants
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Women’s Water-Resistant Pants

If you’re headed outdoors for early-spring or early-fall work, you never quite know what the weather will be. These water-resistant pants are a solid wardrobe workwear staple for women, as they act as snow pants, but aren’t as bulky. They have a fleece lining for warmth, along with a windproof and waterproof outer layer. Bonus: These pants are available in 19 colors and come at an affordable price.

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Mid Weight Vest
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Mid-Weight Vest

A good vest is a staple in the transitional clothing world, and L.L.Bean offers the PrimaLoft Packaway Vest for both women and men. The vest’s core features NASA-developed Aerogel, the lightest material on the planet. It’s wind- and water-resistant, so you’ll stay comfortable in the elements whether using for a spring or fall workwear piece. And when temperatures rise, the vest folds up and packs away into its own pocket!

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Classic Work Glove
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Classic Work Glove

A must-have for transitional clothing, this classic work glove from Backcountry is made of premium grain cowhide, meaning it’s warm, yet breathable. Grabbing a wooden tool? No problem. Need to prune roses? No pokes here! The pull-on style is easy and the elastic cuff provides comfort—no matter your outdoor activity.

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Waterproof Rain Jacket
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Waterproof Rain Jacket

When rain is in the forecast, having a waterproof rain jacket is a nonnegotiable. The drawstring hood ensures you’ll stay securely dry, and the two large pockets store your phone and keys or a spare pair of work gloves. Available in 25 colors and designs, this women’s coat comes with a pouch, meaning it can be folded up and left in your car or truck tool box for when a pop-up shower hits.

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Thermal Underwear Set
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Thermal Underwear Set

Base layers help keep you warm, and this fleece-lined set is like a second skin for those extra-chilly days. The breathable fabric wicks sweat away to keep you comfortable in the case that you’re getting overheated. Plus, the top and bottom offer room for movement, so you have flexibility to move freely while working outside. It’s a workwear must-have for men.

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Waterproof Socks
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Waterproof Socks

Nobody—and we mean, nobody—likes having wet feet. These unisex waterproof socks from Randy Sun are a must-have transitional clothing piece to not only keep your feet cool and dry when the ground is wet, but to wick sweat away from your skin. The socks have a smooth toe seam, so they won’t feel bulky in work boots, and the non-slip ribbed top keeps socks in place. They’re available in 19 colors and four sizes.

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Upf 50+ Sun Protection Shirt
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UPF 50+ Sun Protection Shirt

Even on those crisp days, don’t forget the SPF! This budget-friendly sun protection shirt works well as a transitional clothing piece, as it has an ultraviolet protection factor (UPF) of 50+. The quick-dry fabric wicks away moisture from your skin, the tagless collar and flatlock seams prevent chafing and the long sleeves are light, yet protective. It looks like we all need a sun protection shirt in our closets!

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Cap With Face Mask And Neck Flap
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Cap with Face Mask and Neck Flap

With weather changes come bugs, like pesky mosquitoes, and this foldable sun cap has a face mask and neck flap to not only protect you from pests, but from the sun, as well. Wear it out while fishing, hiking, working in the garden or just sitting around the fire pit at the end of the day. Made of microfiber polyester, it’s soft, breathable and can be adjusted for size. The face mask and neck flap are removable, and the hat has a foldable brim design, so it can be folded up and put away when not being worn.

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