I've Lived Through Brutal Chicago Winters — This Is What You Need to Wear in Below-Freezing Temperatures

Mar. 15, 2025

Photo:Nordstrom Rack (2); Amazon; NordstromWhen people ask me why I left the Midwest, I always say the same thing — the weather.I loathed the extra tasks that came with the cold, likescraping off my carbefore heading to school or shoveling the driveway. That said, I never really minded the clothing, probably because I learned what and whatnotto wear very early on.With several snow and “cold days” under my belt (Yes, they were a real thing!), a year of commuting every day in the Windy City, and 18+ years of living in Illinois, I’ve got the list of essentials you need to dress for 10-degree weather. Keep scrolling to shop waterproof boots, blanket scarves, and more starting at $20.Winter Fashion to Shop NowLillusory Oversized Pullover Sweater, $30 (orig. $46);amazon.comYioioio One-Piece Jumpsuit, $20;amazon.comBcbgeneration Hooded Short Puffer Jacket, $60 (orig. $198);nordstromrack.comSkims Boyfriend T-Shirt, $37 (orig. $46);skims.comBlondo Prestly Waterproof Leather Bootie, $100 (orig. $150);nordstrom.comThe Drop Catalina Pull-On Rib Sweater Pant, $27–$48 (orig. $50);amazon.comMarcus Adler Plaid Fringe Blanket Scarf, $20 (orig. $48);nordstromrack.comUgg Coquette Slipper, $120;amazon.comPilcro The Lennon Wide-Sleeve Turtleneck Sweater, $98;anthropologie.comBcbgeneration Hooded Short Puffer JacketNordstrom Rack$198$60 at Nordstromrack.comWhen it’s really, really cold out, a puffer jacket is unavoidable since fluffy fill makes any coat feel like a portable space heater. However, it also needs thumbholes so I can still use my phone if needed and a neckline that zips all the way up — regular collars are cute but impractical.This one from Bcbgeneration is 69 percent off and comes in eight colors. Three of them also have “liquid” finishes, which is similar to myfavorite Aritzia pufferthat I own in liquid shine matte pearl.The Drop Catalina Pull-On Rib Sweater PantAmazon$50$27 at AmazonYou can’t endure the winter without a supply of sweaters at your disposal, and that goes for toppersandpants, the latter of whichJennifer Hudsonand Jennifer Aniston have worn. I personally feel like sweater pants are more snuggly than denim, and in this case, are cheaper, too.Yioioio One-Piece JumpsuitAmazon$20 at AmazonA short-sleeve jumpsuit in the middle of winter? Before jumping to any conclusions, hear me out: I personally shimmied into a similar one on at least one bitingly-cold day, and it made all the difference. It was an extra layer of warmth, and I don’t think anyone could tell that I was wearing it since it was slim, trim, and nonbulky.That said, you should buy one like this jumpsuit at Amazon that’s notsothin that it’s see-through — and come summer, you can wear it on its own. “It’s flattering, it’s stretchy, and the material is pretty thick. [It] doesn’t feel cheap at all,”wrote one five-star reviewer.Skims Boyfriend T-ShirtSkims$46$37 at Skims.comWhile I often overestimated how cold it was outside, I usually underestimated how hot it’d be wherever I was goinginside. TL;DR: Always wear a T-shirt under your sweaters — I’ll tell anyone who will listen about thisSkims one— in case you need to peel a layer off. And, hey,Jennifer Garnerdoes it, too.Marcus Adler Plaid Fringe Blanket ScarfNordstrom Rack$48$20 at Nordstromrack.comOf course, once you take off your thick sweater, you might just get cold again. My go-to hack: Have a blanket scarf that you can wrap yourself in and wear as a shawl for backup warmth. As for outdoor scarves,hooded onesare pretty useful since they act as a hat-scarf hybrid, and they also minimize the amount of layers you need to take off once you get to your destination.Keep scrolling to shop more cold weather fashion buys from $20 now.Lillusory Oversized Pullover SweaterAmazon$46$30 at AmazonBlondo Prestly Waterproof Leather BootieNordstrom$150$100 at NordstromUgg Coquette SlipperAmazon$120 at AmazonPilcro The Lennon Wide-Sleeve Turtleneck SweaterAnthropologie$98 at Anthropologie

Photo:Nordstrom Rack (2); Amazon; Nordstrom

Nordstrom Rack (2); Amazon; Nordstrom

When people ask me why I left the Midwest, I always say the same thing — the weather.I loathed the extra tasks that came with the cold, likescraping off my carbefore heading to school or shoveling the driveway. That said, I never really minded the clothing, probably because I learned what and whatnotto wear very early on.With several snow and “cold days” under my belt (Yes, they were a real thing!), a year of commuting every day in the Windy City, and 18+ years of living in Illinois, I’ve got the list of essentials you need to dress for 10-degree weather. Keep scrolling to shop waterproof boots, blanket scarves, and more starting at $20.Winter Fashion to Shop NowLillusory Oversized Pullover Sweater, $30 (orig. $46);amazon.comYioioio One-Piece Jumpsuit, $20;amazon.comBcbgeneration Hooded Short Puffer Jacket, $60 (orig. $198);nordstromrack.comSkims Boyfriend T-Shirt, $37 (orig. $46);skims.comBlondo Prestly Waterproof Leather Bootie, $100 (orig. $150);nordstrom.comThe Drop Catalina Pull-On Rib Sweater Pant, $27–$48 (orig. $50);amazon.comMarcus Adler Plaid Fringe Blanket Scarf, $20 (orig. $48);nordstromrack.comUgg Coquette Slipper, $120;amazon.comPilcro The Lennon Wide-Sleeve Turtleneck Sweater, $98;anthropologie.comBcbgeneration Hooded Short Puffer JacketNordstrom Rack$198$60 at Nordstromrack.comWhen it’s really, really cold out, a puffer jacket is unavoidable since fluffy fill makes any coat feel like a portable space heater. However, it also needs thumbholes so I can still use my phone if needed and a neckline that zips all the way up — regular collars are cute but impractical.This one from Bcbgeneration is 69 percent off and comes in eight colors. Three of them also have “liquid” finishes, which is similar to myfavorite Aritzia pufferthat I own in liquid shine matte pearl.The Drop Catalina Pull-On Rib Sweater PantAmazon$50$27 at AmazonYou can’t endure the winter without a supply of sweaters at your disposal, and that goes for toppersandpants, the latter of whichJennifer Hudsonand Jennifer Aniston have worn. I personally feel like sweater pants are more snuggly than denim, and in this case, are cheaper, too.Yioioio One-Piece JumpsuitAmazon$20 at AmazonA short-sleeve jumpsuit in the middle of winter? Before jumping to any conclusions, hear me out: I personally shimmied into a similar one on at least one bitingly-cold day, and it made all the difference. It was an extra layer of warmth, and I don’t think anyone could tell that I was wearing it since it was slim, trim, and nonbulky.That said, you should buy one like this jumpsuit at Amazon that’s notsothin that it’s see-through — and come summer, you can wear it on its own. “It’s flattering, it’s stretchy, and the material is pretty thick. [It] doesn’t feel cheap at all,”wrote one five-star reviewer.Skims Boyfriend T-ShirtSkims$46$37 at Skims.comWhile I often overestimated how cold it was outside, I usually underestimated how hot it’d be wherever I was goinginside. TL;DR: Always wear a T-shirt under your sweaters — I’ll tell anyone who will listen about thisSkims one— in case you need to peel a layer off. And, hey,Jennifer Garnerdoes it, too.Marcus Adler Plaid Fringe Blanket ScarfNordstrom Rack$48$20 at Nordstromrack.comOf course, once you take off your thick sweater, you might just get cold again. My go-to hack: Have a blanket scarf that you can wrap yourself in and wear as a shawl for backup warmth. As for outdoor scarves,hooded onesare pretty useful since they act as a hat-scarf hybrid, and they also minimize the amount of layers you need to take off once you get to your destination.Keep scrolling to shop more cold weather fashion buys from $20 now.Lillusory Oversized Pullover SweaterAmazon$46$30 at AmazonBlondo Prestly Waterproof Leather BootieNordstrom$150$100 at NordstromUgg Coquette SlipperAmazon$120 at AmazonPilcro The Lennon Wide-Sleeve Turtleneck SweaterAnthropologie$98 at Anthropologie

When people ask me why I left the Midwest, I always say the same thing — the weather.

I loathed the extra tasks that came with the cold, likescraping off my carbefore heading to school or shoveling the driveway. That said, I never really minded the clothing, probably because I learned what and whatnotto wear very early on.

With several snow and “cold days” under my belt (Yes, they were a real thing!), a year of commuting every day in the Windy City, and 18+ years of living in Illinois, I’ve got the list of essentials you need to dress for 10-degree weather. Keep scrolling to shop waterproof boots, blanket scarves, and more starting at $20.

Winter Fashion to Shop Now

Bcbgeneration Hooded Short Puffer Jacket

Nordstrom Rack

$198$60 at Nordstromrack.com

When it’s really, really cold out, a puffer jacket is unavoidable since fluffy fill makes any coat feel like a portable space heater. However, it also needs thumbholes so I can still use my phone if needed and a neckline that zips all the way up — regular collars are cute but impractical.

This one from Bcbgeneration is 69 percent off and comes in eight colors. Three of them also have “liquid” finishes, which is similar to myfavorite Aritzia pufferthat I own in liquid shine matte pearl.

The Drop Catalina Pull-On Rib Sweater Pant

Amazon

$50$27 at Amazon

You can’t endure the winter without a supply of sweaters at your disposal, and that goes for toppersandpants, the latter of whichJennifer Hudsonand Jennifer Aniston have worn. I personally feel like sweater pants are more snuggly than denim, and in this case, are cheaper, too.

Yioioio One-Piece Jumpsuit

$20 at Amazon

A short-sleeve jumpsuit in the middle of winter? Before jumping to any conclusions, hear me out: I personally shimmied into a similar one on at least one bitingly-cold day, and it made all the difference. It was an extra layer of warmth, and I don’t think anyone could tell that I was wearing it since it was slim, trim, and nonbulky.

That said, you should buy one like this jumpsuit at Amazon that’s notsothin that it’s see-through — and come summer, you can wear it on its own. “It’s flattering, it’s stretchy, and the material is pretty thick. [It] doesn’t feel cheap at all,”wrote one five-star reviewer.

Skims Boyfriend T-Shirt

Skims

$46$37 at Skims.com

While I often overestimated how cold it was outside, I usually underestimated how hot it’d be wherever I was goinginside. TL;DR: Always wear a T-shirt under your sweaters — I’ll tell anyone who will listen about thisSkims one— in case you need to peel a layer off. And, hey,Jennifer Garnerdoes it, too.

Marcus Adler Plaid Fringe Blanket Scarf

$48$20 at Nordstromrack.com

Of course, once you take off your thick sweater, you might just get cold again. My go-to hack: Have a blanket scarf that you can wrap yourself in and wear as a shawl for backup warmth. As for outdoor scarves,hooded onesare pretty useful since they act as a hat-scarf hybrid, and they also minimize the amount of layers you need to take off once you get to your destination.

Keep scrolling to shop more cold weather fashion buys from $20 now.

Lillusory Oversized Pullover Sweater

$46$30 at Amazon

Blondo Prestly Waterproof Leather Bootie

Nordstrom

$150$100 at Nordstrom

Ugg Coquette Slipper

$120 at Amazon

Pilcro The Lennon Wide-Sleeve Turtleneck Sweater

Anthropologie

$98 at Anthropologie

See More from PEOPLE ShoppingThe 50 Best Amazon Deals Happening This St. Patrick’s Day Weekend — Starting at $7Katie Holmes Can’t Stop Wearing Wide-Leg Jeans — Copy Her Latest Look from $30Amazon’s Fashion Outlet Is Packed with Pretty Celeb-Inspired Dresses Ideal for a Spring Wedding

See More from PEOPLE Shopping

The 50 Best Amazon Deals Happening This St. Patrick’s Day Weekend — Starting at $7Katie Holmes Can’t Stop Wearing Wide-Leg Jeans — Copy Her Latest Look from $30Amazon’s Fashion Outlet Is Packed with Pretty Celeb-Inspired Dresses Ideal for a Spring Wedding

The 50 Best Amazon Deals Happening This St. Patrick’s Day Weekend — Starting at $7

Katie Holmes Can’t Stop Wearing Wide-Leg Jeans — Copy Her Latest Look from $30

Amazon’s Fashion Outlet Is Packed with Pretty Celeb-Inspired Dresses Ideal for a Spring Wedding

source: people.com