No one knows how to dress for winter like an East Coaster. New Jersey–based content creator Allison Whalen is no exception. Her Instagram feed offers a master class in everyday layering, featuring an endless array of luxe sweaters, laid-back flannel, artfully draped scarves, and cozy footwear. "Living in New Jersey, it can definitely get really cold, but I try to make an effort to get outside everyday,” she tells us. "Having warm footwear makes a huge difference in my morning routine.”
Her go-to shoes for surviving even the coldest days of the season without going into hibernation mode are Sperry boots. They’re incredibly comfortable, cozy, and can tackle any terrain, snow included. Read on to see how she’s expertly styling them this season.
"Sperry’s Plushwave 3D Boots are the perfect pick for a winter hike,” Whalen explains of her first look. "They’re so comfortable while still keeping my feet warm! I styled them with an all-black look and a bright-pink beanie for a pop of color!”
"I absolutely love the faux-fur accents on Sperry’s Torrent Lace Up Boots,” Whalen exclaims. "I styled them in a casual, everyday outfit I’d typically wear with snow boots. I think a sweater and leggings with a cute pair of snow boots is the most perfect winter OOTD!”
"I styled these sherpa-lined duck boots for a rainy day spent running errands,” she says of her last look. "I love how the blue in my jacket complements the gray boots!” (We’ll also award bonus points for the well-coordinated umbrella addition.)
SHOP MORE SPERRY BOOTS
These are giving après-ski vibes.
These boots are no match for rainy days.
BRB—we’re buying these for upcoming snow days.
This color-blocking is a 10 out of 10.
This under-$100 pick is so easy to style.
Attention bold dressers: this pair is for you.
-
They're Here: The Fall Shoe Trends That Will Define 2026Finally, shoes are fun again.
-
Attention: The First New It Girl-Approved Boot Trend of Fall 2026 Is HereFollow Selena Gomez's lead.
-
5 Fall Shoe Trends That'll Make Your Jeans Look CoolerDenim is waiting in the wings.
-
From Prada to The Row: The Fall It Shoes That'll Sell Out by September 1Buy one. Buy all.
-
5 Chic Summer-to-Fall Transitional Pieces Fashion People Are Shopping in AugustThe new season is right around the corner.
-
Instead of Black Ankle Boots, This Celeb-Approved Style and Color Will Be Trending This FallÀ la Charlize Theron.
-
The New Fall 2026 Shoes Are Rolling In, and I'm 100% Sure These 33 Pairs Will Sell OutSuede! Satin! Calf hair!
-
Not Flip-Flops, Not Flats—It Girls in NYC Are Wearing Summer's #1 Dress Trend With the Boots That Come Back Every FallThey're thinking ahead.
