What to Pack for Winter Travel

What to Pack for Winter Travel -- From This Is My Happiness Travel Blog

Well, here in California, winter is finally beginning. Thanks to these first glimpses of winter, I’ve been having fun with the layers, textures, and colors of winter outfits. Here are my choices for what to pack for winter travel this season: 

1) Comfortable yet fitted pants

Perfect corduroy pants: My favorite pants of the season are the high-rise skinny cords from J. Crew. They are soft, fit great, and come in a range of either dark or bright colors; I have the forest green ones.

What to Pack for Winter Travel

Perfect slim fit, high rise jeans: I love the high rise of jeans these days because they show off the waist and keep everything feeling tucked in. The fit and fabric of the Madewell and J. Crew ones are nice. I pair them with a flannel or a chambray shirt, a scarf, and an oversized cardigan sweater for an easy day look.

What to pack for winter travel

2) Scarves

What to Pack for Winter Travel

I bring two scarves, a thin one for everyday use and a thick one for extra cold days–this is a great choice for winter–but I would love to have one of these gorgeous travel-inspired scarves from Bird & Knoll ($214).

What to Pack for Winter Travel | This Is My Happiness

Winter colors tend toward black, navy, wine, and forest green, but an easy way to add some style and pizazz to your winter travel wardrobe is to add color. This scarf from Boden, this winter look from J.Crew, or this one from Madewell are colorful favorites.

What to Pack for Winter Travel | This Is My Happiness

3) Black leather riding boots

My secret to finding good boots for travel is to choose flat boots, buy them a 1/2 size up, and wear them with cushy socks and good insoles (a life saver!). These Franco Sarto Cecilia boots are my most comfortable riding boot, perfect for winter travel.

What to Pack for Winter Travel

4) Sweaters

My favorite sweaters of this season are long cardigans that can be worn over layers and are big enough to hide extra winter pounds. 🙂 I love the J. Crew long wool cardigans.

What to Pack for Winter Travel

And I always carry a small cashmere sweater with me–it can be worn under another sweater for extra warmth and is small enough to stuff into a bag when not needed. I especially love the cozy, high-quality cashmere from Everlane. For something less expensive but colorful, check out these basic, inexpensive wool sweaters and these turtleneck sweaters in an array of colors from J. Crew.

Or how about a cape scarf that can be carried in your bag and then pulled on for an extra layer of warmth?

5) Cold weather bottoms

To stay warm on the road, get yourself a pair of fleece lined leggings. They do triple duty as pajamas, a warm layer under pants, and warm tights under a skirt or dress…yes, wearing these means you can wear a skirt in the winter because they look just like tights!


Skirts in the winter thanks to fleece leggings! Merino wool cardigan, chunky scarf, swing T, and wool felt miniskirt all from J. Crew, plus  gloves from Andes Gifts and Franco Sarto riding boots

6) Other essentials:

Comfortable layers:
I layer everything with one of these tanks, which I wear day and night for a little extra warmth. My favorite comfy clothes are these modern takes on the sweatshirt and sweatpants from J. Crew. I bring them to wear in the hotel or even as warm pjs.

What to Pack for Winter Travel | This Is My Happiness.com

Warm outerwear:

L.L. Bean’s down outerwear is a good choice because they are warm and water and wind resistant, yet they don’t take up much space. The down sweater can even be bunched up and stored in its own pocket.

What to Pack for Winter Travel | This Is My Happiness

A classic crossbody purse:

A crossbody purse is a more secure way to carry your things when traveling. I love this large crossbody bag (above) and this small leather crossbody purse (below) from Madewell.


The perfect overnight bag:

I was fortunate to win one of these overnight bags from Lo and Sons during the holiday giveaway on Aviators and a Camera. The price might seem high, but when a bag is this functional and nice looking, it would be money well spent.

What to Pack for Winter Travel

What to Pack for Winter Travel

The Lo and Sons overnight bag has padded pockets for a laptop, shoes, gadgets, and everything else you’d need for a night away

Shop for winter travel items:

What are your favorite pieces this season? What do you pack for winter travel?


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