Winter travel dressing is less about chasing trends and more about choosing pieces that truly work. Cold-weather clothing takes up valuable suitcase space, layers need to function together and outfits should feel comfortable enough for long travel days while still looking intentional once you arrive. The best winter wardrobes are built on a handful of dependable staples that can be worn repeatedly in different combinations without feeling repetitive or bulky.
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Protect Your Hands: Cole Haan Leather Cashmere Blend Lined Basic Tech Tip Gloves
For Charlotte Rose Coleman, a New York City-based celebrity fashion stylist and former fashion editor at O, The Oprah Magazine, winter travel dressing comes down to choosing versatile pieces, such as these gloves, that work harder in your suitcase. "As we age, cold hands can make winter travel incredibly uncomfortable. A cashmere-lined glove provides warmth without being bulky or hard to tuck away. The touchscreen feature also makes it easy as you're checking directions or showing boarding passes throughout your travels. I always suggest a leather glove as it instantly elevates more winter attire. An outfit instantly becomes more polished and less sporty when paired with them," she says.
Go Hands-Free: Quince Italian Leather Patchwork Crossbody Bag
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Warmth You Can Wrap: Aritzia Cashmere Soft
A cashmere scarf is one of the most versatile accessories you can pack, adding warmth while giving you flexibility in how it’s worn. For Rap Sarmiento, a Los Angeles-based fashion stylist and editor, he says it’s an easy way to add interest to travel outfits without overpacking. “The Aritzia Cashmere Scarf adds an effortless pop of color to your travel looks as you might be focused on packing neutrals to make mixing and matching easy,” Rap says. “It can also double as a makeshift hood or pillow on the plane.”
Layer Without Bulk: Uniqlo HEATTECH Cashmere Blend Turtleneck
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Statement Coat That Does It All: Quince 100% Merino Wool Coat
A versatile wool coat grounds winter outfits and transitions easily from casual daytime wear to evening plans without requiring outfit changes. "This Quince Merino Wool Coat pairs with sweats for smoothie runs in the morning, denim and a crew neck during the day, and with a ribbed knit dress and boots for the evening," says Sarmiento.
Cozy Boots Made for Walking: VIVAIA Faux Fur Platform Chunky Wedge Boots
Sometimes, thick socks are not enough to keep your feet warm during the colder months, especially when you’re spending long days walking outside or dealing with unpredictable winter weather. "Picking a lightweight boot (these are fur-lined) is a great option as the sole will keep you safe as you navigate wet pavement or cobblestone streets. Keep in mind that an ankle boot pairs best with a straight-to-wide-leg jean, while a mid-calf boot pairs best with leggings or fleece-lined tights. It's about looking streamlined and chic," says Coleman.
Elevated Cold Weather Pants: Uniqlo Washable Ribbed Knit Pants
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Sources:
Rap Sarmiento is a Los Angeles- and formerly New York City-based fashion stylist and editor. He has worked with celebrity clients including Jamie Chung and Collin Kaepernick and his work has been featured in Vogue Philippines, GQ, Hypebeast, L’Officiel, Maxim, Elle, Elle France and Refinery 29, to name a few.
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