I Never Know What to Pack for Winter Trips, But This Outfit Guide Has Me Covered
Let’s be real: packing for a winter trip can feel like an impossible game of Tetris. Cold-weather vacations require extra warmth, bulky layers, and winter travel essentials that somehow need to fit into a single weekend bag. If you’re planning a long weekend escape to a cozy cabin or a snowy ski resort, it’s all about balancing warm layers, weather-ready outerwear, and practical accessories without overpacking.
Below, I’ve broken down everything you need to pack, from thermal base layers to packable down jackets, so you’ll stay cozy and stylish without sacrificing too much space. Whether you’re headed to New York City, a ski resort, or a winter wonderland, these are the pieces you’ll want in your winter getaway capsule wardrobe.
Thermal Tops and Merino Wool Layers
Long Sleeve Polo
SIMKHAI
$345
This luxurious long-sleeve polo offers lightweight insulation, perfect for layering under sweaters or jackets without adding bulk. A versatile choice for both city strolls and cozy evenings.
Ciao Pullover
LPA
$228
Babes this pullover gives me all the cozy vibes! Perfect to throw over a basic t-shirt before heading off to the airport.
Warm Socks
Aqua Daily Skin Mask 5 Pack
LAPCOS
$20
Although not socks, these hydration masks are essential to keep skin soft and protected from the harsh winter chill, making them a smart add-on to any self-care packing list.
Jocelyn Bow Socks 2 Pack
Lovers and Friends
$26
Adding a set of plush cozy socks is major especially when you are going through TSA. But these socks! I don’t think i would want them to touch
Packable Down Jacket
The Carry-On Roller
by BEIS
$238
While not a jacket, this packable roller is ideal for fitting your bulkier winter items like down jackets and sweaters. It’s compact yet spacious enough to accommodate winter essentials.
Wild At Heart Jacket
BLANKNYC
$148
I like the to be the center of attention sometimes. You know main character vibes. This jacket it perfect for those I want to be over the top travel days.
Faux Fur Coat or Longline Wool Coat
x REVOLVE Lowelle Coat
House of Harlow 1960
$358
This would go perfectly with a pair of ankle boots, leather leggings, and a white long sleeve henley! Chefs kiss for the perfect it’s cold but I want to be cute outfit of the day.
Badu Jacket
LAMARQUE
$395
Several reviewers said that it fits oversized not exactly like the model. But despite that one reviewer stated that she wore this for a winter in paris. And It's definitely giving a winter in Paris vibes.
Ski Pants (for Outdoor Adventures)
The Convertible Weekender in Maple
Beis
$128
Though not ski pants, this vest offers handy compartments to keep essentials close while out on winter adventures. Pair it with your favorite waterproof pants for a ski-ready look.
The Scarlett Ankle Legging
STRUT-THIS
$88
Opt for moisture-wicking, high-performance leggings under ski pants for insulation and flexibility.
Sweaters
Ciao Crew Neck Sweater
SUNDRY
$138
This cozy sweater adds both warmth and a pop of color to any winter outfit, perfect for layering over thermal tops.
Cable Joggers
SIMKHAI
$395
Not technically a sweater, but these luxe joggers offer warmth with a sweater-like texture, ideal for staying cozy at a cabin or chalet.
Fleece Jacket or Vest
Daria Half Zip Sweater
Varley
$288
This zip-up sweater is ideal for layering, with a soft fleece-like feel that keeps you warm without bulk. Great for casual days out or layering for warmth on the go.
Waterproof Boots
Classic Mini II Boot
UGG
$160
Super comfortable and goes will go with all of your travel casual outfits
Sneakers or Slip-Ons
Blazer Low '77 Vintage Sneakers
Nike
$100
Comfortable and stylish, these sneakers are perfect for a casual day exploring or travel days when comfort is key.
Warm Accessories
Malibu Sherpa Cap
Central Park West
$57
This cozy cap adds a chic touch while keeping you warm, ideal for keeping heat in during cold city walks.
Jet Setter Travel Pillow
slip
$99
One reviewer stated Not your average dusty, air port purchased travel pillow.
Compact Travel Bags
The 6pc Packing Cubes
BEIS
$68
These packing cubes allow you to organize and compress your winter layers, helping save space in your luggage.
Classic Fanny Pack
Stoney Clover Lane
$98
Keep essentials close with a compact, hands-free bag perfect for active outings and travel days.
The Carryall Crossbody
BEIS
$68
Perfect for exploring hands-free, this stylish crossbody bag fits all your essentials and is easy to pair with winter outfits.
Winter-Friendly Extras
Jet Lag Deep Hydration Serum
Summer Fridays
$44
Keep your skin hydrated and glowing, even in chilly, dry winter air.
Travel Size Vanilla Skin Hair And Body Mist 3oz
PHLUR
$24 - $38
Stay fresh and moisturized with this travel-friendly mist that’s perfect for colder climates.
