I’ve Survived 10 Chicago Winters—Polar Vortexes and All. This Is the Gear That's Earned My Trust.

Chicago has earned its reputation as a winter tundra, where polar vortexes and lake-effect snow routinely pummel the city. To live here is to adapt to winter, not retreat from it. My days still revolve around “L” train commutes, neighborhood strolls with my kiddo, and exploring tucked-away hiking trails scattered throughout the city—even when temperatures drop to the teens and snow reaches past my ankles. Winter doesn’t stop me from going outside; it simply changes the cold-weather gear I reach for.

The best city-to-trail gear checks several boxes: It layers and works well in a modular system, easily stows when you go indoors, and blends in aesthetically for everyday wear. It also needs to feel comfortable enough to wear all day, from dropping my daughter off at daycare and waiting for the bus to working at the coffee shop or biking to the climbing gym.

For fellow city dwellers who bounce between city sidewalks and dirt trails, these 17 cold-weather essentials are built to handle both.

Best City-to-Trail Gear: At a Glance

Layers

• Patagonia Nano Puff Hi-Loft ($329)
• Fjällräven Keb Fleece Crew Neck ($200)
• Smartwool Second Cut Fleece Jacket ($175)
• REI Midweight Base Layer Top ($55)
• REI Midweight Long-Sleeve Base Layer Tights ($55)
• Patagonia Nano-Air Light Bottoms ($229)

Footwear

• Vivobarefoot Explorer Mid JJF ($230)
• Danner Mountain 600 ID GTX ($250)
• Kahtoola NANOspikes ($64)

Accessories

• Smartwool Second Cut Mittens ($65)
• Hestra Axis Gloves ($110)
• Hestra Gravita Merino Liner ($55)
• Turtle Fur Chelonia 150 Fleece Beanie ($22)
• Turtlefur Chelonia 150 Neck Warmer ($20)
• MiiR 360 Traveler 16oz ($33)
• Thule Stroller Footmuff ($180)
• Ombraz Cammina Sunglasses ($160)

Layers

Patagonia Nano Puff Hi-Loft

A synthetic, insulated jacket designed for chilly and windy weather

$329 at REI (Women’s)

$329 at REI (Men’s)

This synthetic insulated jacket is my go-to for city living, especially when fending off the unpredictable winter weather we have in Chicago. When temperatures drop to near freezing, this jacket delivers serious warmth thanks to the lightweight PrimaLoft Silver insulation, and a durable water repellent (DWR) shell fabric sheds light rain and snow. Its boxy shape provides plenty of room for extra layers underneath.

Fjällräven Keb Fleece Crew Neck

A breathable and durable fleece midlayer

$200 at Fjällräven (Men’s)

This is not your average sweatshirt. I think of it more like a Swiss Army knife of a sweater—moisture-wicking and breathable, built to handle wear and tear, and seriously comfortable. It’s reinforced with Fjällräven’s G-1000 on the shoulders and durable polyester and wool blend elsewhere. I throw it on as a midlayer for winter hikes and quick errands alike, either on its own on warmer days or under an insulated jacket if it dips into the 40s or below.

Smartwool Second Cut Fleece Jacket

A super soft fleece jacket made from respun recycled wool

$105 at Smartwool (Women’s)

$105 at Smartwool (Men’s)

What looks like a no-frills fleece comes with a sustainability story worth mentioning. Smartwool crafted this full-zip fleece using pre-consumer scraps form their Classic Thermal Merino Base Layers. Made from 75% upcycled content, the production of this fleece saves 350,000 pounds of material from going to the landfill. The wool delivers the same softness and warmth as brand-new merino. I wear this fleece on its own on daily walks and bike commutes in slightly warmer weather or while hiking as a midlayer underneath a waterproof shell.

REI Midweight Base Layer Top

A midweight baselayer long sleeve that’s equal parts stretchy and warm

$55 at REI (Women’s)

$55 at REI (Men’s)

Five years ago, this baselayer top flipped my whole winter layering mindset upside down. I’d always been told merino was the only way to go. No exceptions. But as a more casual outdoor enthusiast who prioritizes comfort and tends to find merino itchy—and is picky about what’s actually worth the splurge—I took a chance on this polyester midweight top. Turns out, I have zero regrets. This base layer is a true staple for my winters. If I’m outside for longer stretches in the cold, it’s on. Plus, it’s rare to find a long sleeve top for $55, especially one that’s comfortable for everyday wear.

REI Midweight Base Layer Tights

A matching bottom baselayer built for cold-weather layering

$55 at REI (Women’s)

$55 at REI (Men’s)

These base layer tights feel more like stretchy, fitted PJ bottoms than plasticky synthetic leggings. And that’s why I love wearing them. They’re so dang comfortable and truly, the Goldilocks of leggings—not too tight, not saggy, but just right. I love them just as much for chilling indoors at a cabin getaway as I do for cold-weather hiking.

Patagonia Nano-Air Light Bottoms

Lightly insulated, breathable pants designed for cold cold-weather adventures

$229 at Patagonia (Women’s)

$229 at Patagonia (Men’s)

Trust me when I say I wear these pants most days of the week. From brisk walks through Chicago’s parks or lounging on the couch after a long day of work, these insulated pants have become a favorite in my everyday wardrobe. They balance breathability and warmth thanks to insulation on the front and back of the legs with stretchy side panels that allow vapor to escape when I’m working up a sweat.

Footwear

Vivobarefoot Explorer Mid JJF

An insulated, flexible winter boot with a barefoot-style feel

$230 at Vivobarefoot (Women’s)

$230 at Vivobarefoot (Men’s)

These unique winter boots are as comfortable as they are rugged. I tend to avoid clunky, heavy shoes (especially when I’m so frequently on-the-move in the city), so standard winter boots are a “no” for me. The Vivobarefoot Explorer Mids have become my favorite winter shoes for both neighborhood walks and urban hiking. When streets are icy and temperatures hover near freezing, they keep my feet warm while still feeling natural and flexible underfoot. The wide toe box actually lets my toes splay the way they’re supposed to, which provides more stability and balance compared to any other boots or shoes I’ve worn in winter.

Danner Mountain 600 ID GTX

A waterproof hiking boot built for wet conditions

$168 at REI

$250 at Backcountry

On days that blur commuting, social plans, and winter weather, I bring these waterproof Danners along. They’re built like a hiking boot, fit like a shoe, and look right at home at a concert or dinner. I commute in them on blustery winter days and keep them laced up long after the workday ends when I’m out with friends. And despite the dozens of miles I’ve put on them this season, I haven’t noticed any wear and tear in the suede or soles.

Kahtoola NANOspikes

Stretchy crampons that provide low-profile traction on icy sidewalks and packed snow

$64 at REI

$64 at Kahtoola

After snowstorms, these come out of storage fast. The tungsten carbide spikes add instant traction on icy sidewalks and have spared me several very public (and painful) slips on slick pavement. And I appreciate how easy they are to slip over the soles of my boots and shoes. I went with size small NANOspikes since I wear an 8.5 women’s shoe, but I wish I had opted for the medium. I recommend sizing up one size if you’re on the cusp, especially if you plan to wear them over bulkier winter boots or thick soles.

Accessories

Smartwool Second Cut Mittens

Cozy mittens made from upcycled wool

$65 at Smartwool

These mittens are a solid choice for anyone who values simple, sustainable gear. Using respun wool just like the Second Cut Fleece, Smartwool’s Second Cut Mittens have been a newfound favorite of mine for more casual activity in the city—like pushing the stroller or walking to the train in biting wind. The fabric around the thumb is a bit chunky for texting, but the touchscreen leather on the palm and thumb actually work way better than I expected.

Hestra Axis Gloves

A lightweight glove insulated with PrimaLoft

$110 at Hestra

In Chicago, we’re more used to sopping sleet than powdery snow. Trust me: I’ve been drenched on my way to the train more times than I can count. The Hestra Axis has proven the value of a water-resistant glove in my winter wardrobe. I say “wardrobe” because these gloves are sleek and style-forward (more so than your techy ski glove). Yet like a ski glove, the water-resistant nylon fabric and PrimaLoft Gold insulation keeps wetness out and locks heat in.

Hestra Gravita Merino Liner

Thin yet ultra-warm merino wool liners with tech-touch fingertips

$55 at evo

$55 at Hestra

When the temps really drop in the city, I slip these featherlight liners under my Hestra Axis gloves for a noticeably warmer system. They fit so seamlessly around my hand, I sometimes forget I’m even wearing them. And whenever I start to heat up, I ditch the outer glove and rely on the liners alone. I also appreciate the tech-touch fingertips that make it easy for me to text while waiting for the bus or swiftly tap to the next song on my default biking playlist.

Turtle Fur Chelonia 150 Fleece Beanie

A super soft, microfleece hat designed to retain heat but avoid overheating

$22 at Turtle Fur

You’ll be hard-pressed to find softer fleece than Turtle Fur. The Chelonia 150 Beanie is a stretchy, low-profile hat that hugs your head and is reliably warm. It also packs down small, disappearing in your backpack without adding too much bulk. I love rolling up the cuff of this hat to turn it into a fisherman beanie too, especially when I work up a sweat on urban trails or daily commutes. Or to just look cute.

Turtle Fur Chelonia 150 Neck Warmer

An ultra-soft neck gaiter that blocks wind and traps warmth

$20 at Turtle Fur

When the wind is whipping—and inevitably chapping my cheeks—I pair this Turtle Fur neck warmer with the hat above to protect my face and stay snug. Its double-layered design is one of the warmest I’ve found, and it does wonders at keeping the wind off exposed skin. I’ve worn other neck warmers that are either itchy (usually wool) or are super tight and practically choke me. With the Chelonia 150 Neck Warmer, that’s not the case.

MiiR 360 Traveler 16oz

Leakproof, insulated travel mug that keeps drinks hot for hours

$33 at MiiR

$33 at Amazon

Cold walks and chilly playground pit-stops are better with hot coffee in hand. This bottle keeps drinks warm for more than 10 hours at a time (seriously, I forgot my coffee on the counter and discovered it after a full day’s work—still warm), easily slips into the side pocket of my backpack, and fits perfectly in my car cupholder. What more could you ask for in a travel mug?

Thule Stroller Footmuff

An insulated, weather-resistant stroller cover that keeps kids warm

$180 at Thule

$180 at Amazon

This stroller add-on has made daily walks in our Thule Urban Glide stroller far warmer—and longer. The zippered insulated pouch keeps my 10-month-old daughter comfortable no matter how far we roam, plus we avoid the hassle of readjusting a blanket every few minutes that would normally slip off while strolling.

Ombraz Cammina Sunglasses

Armless sunglasses that stay put without irritating your ears

$160 at Ombraz

On sunny yet snowy days, these sleek sunglasses make a noticeable difference. The strap fits easily under hats and hoods without irritating your ears, and the polarized lenses fend off UV rays reflecting off the snow. You can also order them as light-transitioning prescription glasses (from $540) that darken when you go outside.