4 Stylish Boot Outfits to Save for Cold Winter Days

Boots are to winter wardrobes as bikinis are to summer. I really can’t get through one chilly week, let alone the holiday season, without them. This year, I’m especially into the chunky-sole trend, which first bubbled up last year and luckily, has stuck around. I have my eyes on two particular styles from Sperry that I found at Nordstrom while doing a little winter shopping (as one does). I’m into these pairs for cold winter days, especially when the weather can be a bit less predictable than I’d prefer. One is a shearling lace-up style, and the other is a chunky Chelsea ankle boot. And don’t worry—I’m sharing exactly how I’d style them for every upcoming winter occasion.

Holiday Gift Shopping

chunky shearling boots


While I’m not a fan of crowds, I am a fan of buying gifts in person. Sometimes you just need to feel a sweater to know if it’ll be soft enough for your mom, or you need to smell a perfume to decipher if it has just the right amount of floral notes for your best friend. Since a day of shopping in any city can be a bit hectic, I like to focus on my wardrobe to help me feel prepared.

My footwear must be warm and comfortable since I'll likely be on my feet for hours at a time, which is why I love these black shearling-lined, lace-up boots. While my gut says to wear the boots with denim, a matching-leather-pants-and-top situation feels a bit more luxe. Another nonnegotiable on a busy day is a crossbody bag that not only holds my sunglasses, hand sanitizer, and maybe even a snack or two (don’t @ me) but also allows me to be hands-free while picking out gifts.

Travel Day

winter travel day outfit


I’m planning a ski trip with friends this winter, and I will absolutely be packing the Torrent Boots for the occasion (in both colors if you’re wondering). The traction on the sole means that even my clumsy self won’t slip, and the suede material is actually waterproof, so I won’t ruin my boots even if I do.

For my travel day to said ski destination, I’ll wear the boots to save room in my suitcase (and also so I’m ready to go upon arrival). For maximum comfort, I’ll pair them with a cozy knit set, a fuzzy jacket, and a shearling-trimmed travel tote that complements the boots pretty damn well, if I do say so myself.

Annual Gift Exchange

rain boots outfit


My childhood friends and I always do a gift exchange when we’re back home in late December, and the unofficial dress code is “holiday casual.” The crystal buttons on the sweater and the beaded bag give the look a festive feel, while the light-wash denim, rubber boots, and classic wool coat keep things a bit more low-key.

The ankle height of these Chelsea boots makes them the perfect candidate for all of my winter denim outfits, even more so on rainy days. Plus, I love that they come in a range of colors, including this black-and-purple combo.

Holiday Lights Tour

chelsea boots outfit


By mid-December, just about every house in my neighborhood has decorations up. I usually make a whole evening out of walking around with friends to judge—I mean look—at all of them.

These Chelsea boots are ideal for a night spent outdoors and are no match for a little evening rain or even unexpected sprinklers. (Hey, it’s happened to me before.) They look so cute paired with a sweater dress, but at night I’ll be extra bundled up with a coat and beanie, too.