Truth be told, winter is one of my favorite and least favorite times to travel. It’s a favorite because it’s festive, and it’s least because packing for winter trips is a beast. Between the sweater, jeans, coats, boots, and accessories, I could easily fill my entire sizable carry-on suitcase with one day’s worth of clothes. But since wintertime travel is a fact of life, I’ve done my best to figure out what the travel-friendly cold-weather essentials are that’ll make life a bit easier (and more stylish, of course). I suppose that it’s worth noting that I rarely carry-on a bit in the winter, opting to check a larger suitcase instead. (If you can carry-on on the winter, please tell me your secrets.)
If you have winter trips on your roster, which I’m assuming you do since you’re here, I’m here to offer up some pre-travel shopping and packing advice. Below, I’ve highlighted the TK items I pack for every winter trip I take. Take note and feel free to shop items you may be missing, as I’ve included my favorites in each category.
An Oversized Scarf
Don’t worry about this item taking up your in-demand suitcase space. You’ll want to wear it on the plane. An oversized scarf doubles as a blanket in-flight and as a neck warmer outside.
J.Crew
Cashmere Whipstitch Oversized Wrap Scarf
White + Warren
Cashmere Travel Wrap
Vince
New Boiled Cashmere Knit Blanket Wrap
Lightweight cashmere sweaters
The beauty of cashmere is that it’s warm but fairly thin, so it’s an excellent sweater option to pack.
Reformation
Dana Cashmere Crew Sweater
J.Crew
Brushed Cashmere Shrunken Crewneck Sweater
Naadam
The Original Cashmere Sweater
Warm Tights
If you want to pack some dressier outfits for dinners and such, skirts or dresses paired with warm tights will take up less luggage space than, say, trousers and a sweater. You can also wear tights under thinner pants for extra warmth, so they do double duty.
Reformation
Swedish Stockings Olivia Premium Tights
Falke
Warm Deluxe 80 Tights
Commando
Fleece Lined Opaque Tights
Loafers
Loafers take up less space than boots and especially when paired with socks, they can provide considerable warmth—and they go with everything.
G.H.Bass
Whitney Leather Loafers
Reformation
Ani Ruched Loafers
Prada
Triangle Logo Loafers
“Packable” Jackets
Certain jackets provide plenty of warmth but miraculously smoosh down to take up minimal space. Free People makes on that I’m particularly fond of.
Free People
FP Movement Pippa Packable Puffer Jacket
The North Face
Nuptse 1996 Packable Quilted 700 Fill Power Down Jacket
Halfdays
Nellie Packable Puffer Jacket
Long-Sleeve Layering Tees
Layering tees take up zero space, provide extra warmth, and can be worn again and again throughout your trip. My advice is to pack a few—trust me, you’ll wear them.
J.Crew
Collection Sheer Wool-Blend Long-Sleeve T-Shirt
Aritzia
HomeStretch Crew Longsleeve
Nordstrom
Stretch Pima Cotton Long Sleeve T-Shirt
A Chic Belt
When traveling, it’s smart to stick to basics that you can wear multiple times. Adding in accessories such as a belt will make your outfits feel special.
Déhanche
Hollyhock Mixed Metal
Madewell
Triple Keeper Suede Belt
Mango
Leopard-Print Leather Belt
Medium-Wash Mid-Weight Jeans
It’s best to pack just one or two pairs of jeans when packing for winter. If just one, I suggest a versatile medium-wash pair that’s mid-weight as opposed to bulky heavy-weight.
Agolde
Ren: High Rise Wide Leg Jeans
Madewell
The Darted Barrel-Leg Jeans in Irmo Wash
Bold Earrings
When you’re wearing sweaters, coats, and scarves, the best jewelry to wear is a pair of gold earrings that’ll still stand out among all of the fabric.
Reformation
Evelyn Earrings
Jenny Bird
Florence Earrings
Completedworks
Gold-Plated Earrings
A Dark-Colored Shoulder Bag
In the winter, I usually opt for shoulder bags that work with coats and sweaters. And when traveling, a dark-colored neutral bag is my go-to so that I only have to pack one bag.
Saint Laurent
Le 5 à 7 Supple Small Leather Shoulder Bag
Elleme
Trousse Suede Shoulder Bag
