If you ask anyone what their favorite winter shoe was in the early 2000s, I'm 99.9% sure that the answer would be some variation of cozy boots. When I look up fashion from this decade, the results are filled with paparazzi-snapped photos of It girls wearing chunky, fleece-lined suede boots with low-rise miniskirts, velour tracksuits, and baggy jeans on the streets of Los Angeles (and even on red carpets). The love for this shoe style was so real that people sported them even in the middle of the summer despite their obvious winter appeal. Twenty years later, this design is back in the trend cycle with a vengeance, and celebrities and influencers everywhere are making sure that we all know that fashionable, cozy footwear is in.
Now that the holiday season is officially here, I'm setting my sights on the Koolaburra by UGG collection at DSW. Not only are there options for literally every person in my family, but I'm also a fan of this price point (especially because I plan to buy more than just one pair). Influencer Angela Kim agrees that these are the shoes to buy and gift this season, so I'm following her lead and adopting this vibe for winter.
All it takes is one scroll through Kim's Instagram to see what a chic full-time mom she is. Her style is relaxed and on-trend with a bit of L.A. flair, and this outfit is the epitome of that. A moment, please, for the practicality of this look: Who doesn't want to slip on a pair of leggings, cozy shoes, and an oversize sweater every day during the winter? But the real magic here lies in Kim's ability to turn this look from one that screams "laundry day" into a full-fledged fashion-forward ensemble. The neutral oversize cardigan is about as on-trend as it gets, and of course, these new-season styles from Koolaburra are the perfect modern take on the beloved early-aughts shoe trend.
Whether you're looking for classic cozy boots or other trending faux fur–lined footwear (hello, Advay Boot), the Koolaburra line is ready for you. Want to see what Kim and I are shopping at DSW this winter? Just keep scrolling for our picks.
Shop More Koolaburra by UGG Favorites
A classic.
The sandal version of my favorite black puffer jacket? I'm sold.
Don't sleep on the gray colorway.
Don't skip out on the men's section. These would pair well with baggy jeans and a chunky knit.
Peep the fur lining. Does it get any warmer than this?
You can fold these over for a faux-fur moment.
How cute are these bows?
I love a functional zipper.
I'm already gushing at the thought of my cousins unboxing these this year.
Snow days have nothing on these boots.
A comfier alternative to your typical combat boot.
Here's more proof that these bows add the perfect touch.
I'm officially ready to cozy up by the fireplace.
One for you, and one for your mini-me.
The black pair is a must.
Winter clogs for the men in your life.
Cozy shoes don't have to be boring. This is proof.
I consider these slippers an essential. This is a gift your dad, brother, or significant other will never take off.
-
Move Over, Jeans—The Chicest People I Know Are Wearing This Expensive-Looking Pant Trend With BootsSpotted on Naomi Watts.
-
These Are the Surprising Shoe Trends Gen Z Is Styling With Everyday Outfits for the Rest of 2025Niche, weird, and unconventional.
-
Forget Flats—Everyone With Good Taste Is Wearing These Boots With Jeans and a JacketPut these on your shopping list.
-
Listen, Being Cool in 2025 Requires Just Two Things: Loose Jeans and This “Weird” Viral Flat-Shoe TrendThey're strange, but so chic.
-
These Easy Outfit Formulas Make Even Fall's Most Polarizing Boot Trend Look CoolSee the inspiration inside.
-
This Is the Luxe Fall Shoe Trend Every Fashion Person Is Already Wearing on RepeatCount these inspo pics as proof.
-
It's Controversial (I Know), But Frequent Fashion Flyers Swear By This Jeans Outfit for Long FlightsIt involves an elegant leather coat and chic luggage.
-
Taylor Swift Just Wore the Skirt-and-Boots Combo That Screams '90s Jennifer AnistonIt's foolproof.
