The holidays are right around the corner, which means it’s time to pull out of your favorite sherpa-lined Ugg boots. These iconic shoes took over in the 2000s and made the ultimate comeback just a few years ago, in 2022, with the release of the Bella Hadid-approved Classic Ultra Mini Platform (which just so happens to be my favorite, too).
Yes, Ugg boots are known for their undeniable comfort, but can we talk about how cute they are, too? The silhouette makes them the perfect winter boot, keeping you cozy no matter what the elements bring. And with so many styles and colors to choose from, there’s no need to stop at just one pair—from boho ensembles to chic airport looks, the outfit possibilities are limitless. Not quite sure what I mean? I found 14 outstandingly chic (and incredibly wearable) looks from street style stars and celebrities, including Bella and Gigi Hadid, Jennifer Lopez, Emily Ratajkowski, and Selena Gomez, to provide you with ample Ugg boots outfit inspiration for your next cold-weather look. See and shop them all below.
Trendsetting Basics
Running out of the house in your loungewear doesn’t have to be basic. (Of course, when it’s Bella Hadid wearing a look, it’s anything but basic, but I digress…) Whether you’re opting for the no-pants look or not, throw on your favorite sunnies, a leather jacket, and platform Uggs for a more stylish take on grabbing a sweet treat from the bodega or your favorite cafe. After all, iced lattes always taste better when you’re wearing a cute outfit.
Prada Black Runway Sunglasses
Now 10% Off
Free People Vinny Vegan Bomber
Alo Yoga Icon Ribbed Boyshort
Now 32% Off
Alo Yoga Unisex Scrunch Sock
Now 32% Off
Ugg Classic Ultra Mini Platform Boot
Sherpa Season
This is one of my favorite times of the year—when you can feel wrapped up but not overly so. A vest is the perfect option for this weather, and in shearling? Sign me up. Pair it was a classic pair of jeans and a patent leather bag à la Gigi Hadid, and you’re all set for just about anything.
Gucci Oval-shaped Sunglasses
Isabel Marant Gwendalia Wool-Blend Vest
Now 30% Off
Ralph Lauren Relaxed Fit Striped Cotton Shirt
Now 16% Off
Levi’s Ribcage Full Length
Ugg Tazz Platform Slipper
Versace Croc-Effect Medusa ’95 Small Handbag
Cheetah Girl
In my opinion, animal prints like leopard and cheetah prints are a sartorial neutral. I own this exact pair of pants and can confidently say they’re part of my weekly rotation. The beauty of these is that you don’t need much else to make them look chic. Add an oversized bomber jacket, sunnies, and, of course, your favorite style of Uggs, and you have yourself a cute and comfortable fall ’fit.
Acne Studios Bomber Jacket
Courrèges Black Holistic Tank Top
Vivienne Westwood Large Hazel Handbag
Ugg Classic Ultra Mini Platform
Cute and Cozy
Heels? No, thank you. Uggs with a lift? Yes, please! Give yourself a boost with a pair of Uggs that have an extra platform. Dress them down for a football game or up for a day of holiday shopping.
Chloé Gold Carlina Sunglasses
Eterne Butter Rib Cropped Fitted Turtleneck Top
Free People CRVY Gia Wide-Leg Jeans
Ugg Classic Short New Heights
Astrid & Miyu Dome Huggies in Gold
Now 26% Off
Elevated Comfort
Being comfortable doesn’t always have to equate to wearing sweatpants and a hoodie. Dress up your loungewear look with a cozy cashmere set that will keep you as warm as your favorite blanket.
Balenciaga Black Wrap D-Frame Sunglasses
Now 21% Off
Vince Oversized Double Knit Cardigan
Naked Cashmere Gina Midi Skirt
HUE Mini Crew Sock 6-Pack
Ugg Classic Ultra Mini Platform Boot
Chic Athleisure
Whether you’re running to a workout class or just wanting to feel relaxed, try upgrading your athleisure ensembles with a wool wrap coat, leather gloves, and Uggs. You’ll stay incredibly snug while remaining stylish. It’s a win-win in my book.
Everlane The Cloud Oversized Turtleneck
Now 30% Off
Alo Yoga 7/8 High-Waist Airbrush Legging
Now 31% Off
Michael Kors Wool Blend Wrap Coat
Coach Sculpted Signature Leather Tech Gloves
Ugg Bailey Button II Boot
Now 29% Off
Astrid & Miyu Essential Dome Ring
Now 25% Off
Bright Trench
I normally turn to shades of black and white for the winter months, but I can’t get over how cute this yellow trench is. A bright piece of outerwear like this is sure to boost your mood on a rainy day, and paired with a color-block sweater, it really solidifies the look.
Norba Trench Coat Electra
Saodimallsu Womens Striped Cropped Sweater
Agolde Low Slung Baggy 30.5”
Kate Spade Dakota Small Crossbody
Skirt Season
I am a sucker for a midi skirt—even in the colder months. Make it more weather-appropriate by adding a cinched jacket and a pair of tall Uggs to make for a warmer, cozier approach. And in case you need another layer, might I suggest a pair of burgundy tights?
Celine 52MM Oval Acetate Sunglasses
Aritzia Cozy Fleece Snug Hi-Rib Zip Hoodie
Now 20% Off
Lisa Says Gah Maeve Midi Skirt
Ugg Classic Mini Dipper Cozy Ankle Boots
Gabriel & Co. 14K Yellow Plain Gold Diamond Cut Stackable Ring
Streetwear Ready
Distressed denim was seen all over the runways last season and it’s clear that this trend is here to stay for a while. I particularly like this style when it is in more of a baggy silhouette, which gives off that effortless, cool-girl vibe. It’s the perfect way to give your Uggs a streetwear-ready touch.
Modern Citizen Halle Vegan Leather Jacket
Meshki Aurelie Cut Out Short Sleeve Top
Jaded London Acid Brown Colossus Jeans
Now 12% Off
Tory Burch Kira Diamond Quilt Convertible Shoulder Bag
Ugg Classic Ultra Mini Platform Boot
Rumored Endless Love Hoops
Everything but The Suitcase
Now that the holidays are here, the time has come to build our stylish airport outfits. Enhance your airport look with a pop of color–if it won’t fit in your suitcase, wear it instead. Layering adds a unique flair to your look while balancing versatility, so why not give it a try?
Coach C Hardware Round Sunglasses
Marni Yellow Brushed Alpaca Scarf with Fringes
The Frankie Shop Black Astra Bomber Jacket
Naked Wardrobe French Cotton-Terry Oversized Hoodie
Skims Boyfriend Loose Wide-Leg Pants
The Mini Skirt
If it isn’t too cold outside, why not show a little leg? Bubble skirts are my new go-to wardrobe staple, and they’re so easy to style and look chic—regardless if it’s dressed up or down. Grab your favorite button-down and throw a warm knit on top. Trust me, double collars are in.
Frame Relaxed Cotton Shirt in Light Blue
Now 35% Off
Citizens of Humanity Simone Polo Sweater
Grey Lab Bubble Hem Scuba Drawstring Miniskirt
Now 30% Off
Ugg Classic Twin Seam New Heights Boots
Vince Vince Double Layer Wool & Cashmere Sweater
Now 25% Off
Frank & Eileen Patrick Popover Henley
Business Casual
Who said Uggs can’t be part of your workwear? We’ve all had those work weeks where we made poor footwear choices for the daily commute and just needed something that wouldn’t add to the aches. So why not try a pair of platform Tazmans with your best blazer and trousers? Keep it professional without sacrificing your comfort.
Le Specs Unreal 52mm Rectangular Sunglasses
Now 20% Off
Gabriel and Co 14K Yellow Gold Open Circle Pendant Necklace
Banana Republic Barathea Relaxed Italian Wool Tuxedo Jacket
Banana Republic Barathea Italian Wool Tapered Tuxedo Pant
Leatherology Greta Chain Small Pochette
Ugg Tazz Platform Slipper
Layered Look
If you didn’t know, layering is key for this season, and we have Miuccia Prada to thank for that. Her latest collection has inspired many to think above and beyond and get creative with their aesthetic. Start with a skirt and sweater base layer, then build from there. The world is your oyster.
J.Crew Oval Buckle Belt in Italian Leather
Now 30% Off
LoveShackFancy Donna Skirt
Intimissimi Wool & Cotton Long Sleeve High Collar Top
Prada Buckle Large Leather Handbag with Belt
Ugg Classic Chillapeak Tall Boot
Chunky Scarf
A chunky scarf is the best accessory to enhance warmth and style during the colder months. Pair it with your favorite trench and trousers for an effortless, yet cozy look.
Grey Bandit Meadows Scarf
Proenza Schouler Faux Leather Trench Coat
Now 70% Off
Quince Mongolian Cashmere Crewneck Sweater
Reformation Alex Mid Rise Pant
Ugg Ultra Mini Classic Boot
Astird & Miyu Bold Pavé Huggies
Now 26% Off
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