Stylish, Comfy Travel—The Winter Edition!

Casual Attire

The secret to chic, comfortable style while traveling in winter

Travel during the wintertime often revolves around holiday gatherings and vacation getaways to either snowy, ski-type destinations or warmer, beachy-type climes. Looking chic in an easy, understated, and comfy manner while traveling just feels good, emotionally and physically. Read on to uncover the secrets behind this stylish mode of dress and how you can look fabulous on your next winter adventure.

If you’ve read my article, “The Art of Stylish Comfy Travel–A True Game-Changer,” you already know that dressing stylishly (and comfortably) while traveling means you’ll look great, and you’ll feel great. In other words, your confidence will soar, dressed in stunning simplicity. And who doesn’t love that feeling?

Those who know me won’t be surprised that I encourage an all-black color palette. From a practical standpoint, it is terrific in terms of hiding any spots you might incur in transit. And in terms of chic, I am pretty sure nothing more needs to be said. The visual impact of black is massive, and the ease with which you can put your look together is almost mind-boggling.


Travel Bottoms

So, what does a winning winter travel look consist of? It can go several ways, but let’s start with my favorites: leggings, yoga pants, wide-leg pants, and cozy joggers. (The joggers are adorable and pack so much punch!) When choosing your bottoms, be sure that they are fresh-looking and not what you have been living in at home. You want to look pristine, polished and pulled together.

For fall and winter travel, I highly recommend a cashmere bottom as your first choice of fabrication. Leggings, joggers, flare, and wide-leg pants are all available in cashmere, and this soft, cozy fabric will be a treat that you will savor.

If you prefer jeans, go for it, but remember that you want to be comfortable, and snug jeans are not always so when traveling. Also, you should know that when flying, doctors recommend clothing that “gives” to compensate for swelling that occurs with altitude. Finally, if you do choose the jeans route, go with bootcut/flare jeans, as they appear more put together.

Travel Tops

You likely already know that I am a fan of fluted T-shirts that are a little longer in length. This A-line silhouette is flattering on every body shape. And when choosing a color, go with black or white.

Layering is essential here as you don’t know what the temperature on the plane will be. Generally, I find it to be freezing cold. Still, occasionally it is overly warm so having the T-shirt to layer with is a help. And if you are traveling from a cold locale to a warm-weather destination, being able to shed your layers down to a T-shirt is essential.

Sweaters are key in this situation—for the obvious reason. I love and lean toward looser, fluted sweaters. Sometimes they are cropped, and sometimes they are tunic-length—both are figure-flattering, forgiving, comfortable, and chic.

The tunic sweaters you’ll see in the shopping are adorable worn over a white T-shirt. They can be worn as a top for your third piece or tied around your waist or shoulders. They are also perfect for layering to accommodate fluctuating in-flight temperatures and make for an easy transition when you arrive in the tropics—or wherever your adventures take you. I just know you’ll love them!


Third Pieces for Cold-Weather Travel

If you’re unfamiliar with the term, a “third piece” is the last thing you put on that completes and polishes your look. I like to think of the third piece as the “glue” that pulls your chic look together.

The cardigans I’ve shopped for in this category pair easily with T-shirts and will keep you cozy in flight. And if you are headed to a more temperate clime, an oversized denim jacket worn or tied at the waist is another way to go. The contrast of the denim with an all-black color palette really pops the look.

Having said that, since we’re talking primarily about cold-weather travel, I think you should consider a peacoat to finish your look. This would be in place of a denim jacket and can be easily worn over a pullover or cardigan sweater. This timeless double-breasted jacket is ever-so-chic and a versatile piece you will use all winter.

One more option is the puffer jacket which is practical and adorable if you travel to the mountains for snow. Regardless of what you gravitate toward, all of the third-piece items I’ve shopped for you will serve you well in your winter travels.


Travel Accessories

The most important part of your accessorizing is your travel tote. This essential piece will not only serve you well for travel but in your everyday life. Your tote bag should be an investment piece and a lifetime purchase, so find one you are possessed by, treat it well, and you’ll have it forever!

Of course, I’ve shopped some extraordinary totes for you along with a few other essential items you’ll want to carry. These include a black cashmere wrap to keep you in luxurious warmth during your travels, travel organizers, wallets, card holders, cashmere socks to keep your feet toasty, noise-canceling headsets, jewelry organizers, an umbrella, and more.

I’ve also pulled together a few fabulous accessories that will polish your look as you travel in chic comfort.



When it comes to what you wear on your feet, comfort is essential. I always go with flats, except when I choose to wear ankle boots. Keep in mind that if your boots are designer-quality, they will be super comfortable—even with heels.

With that in mind, if you are traveling to a warmer climate from a colder one, I recommend wearing boots and carrying a yummy pair of flat sandals in your travel tote. Then, when you land, you can do a quick change and depart the plane ready for the environment you’ve traveled to. This way, you’re comfy on your journey and comfy when you arrive.

Now back to boots. This time of year, they are obviously your ticket to staying warm. If you are wearing leggings, you will want a mid-calf to knee-high boot, and you want them to be flat. Lug-sole boots are such fun and add an edgier look to this timeless combination. This is an all-time favorite of mine for many looks, including joggers.

At home, these boots will create adorable combinations with your skinny jeans tucked in and wide-leg jeans worn over them. You can even use them with skirts, and they are stunning with a midi sweater dress, one of this season’s hot tickets.

If you choose to wear joggers, flare, or wide-leg pants during your winter travels, ankle booties, flat boots with a lug sole, or pointy-toe booties will complete your look easily and chicly.


If you are planning to travel this fall and winter…

And I hope you are, any and all of these easy-to-combine and timeless treasures are winners for sure.

Have so much fun as you gather pieces to serve you in your travels and beyond!

As you peruse all the shopping in this post, keep in mind that things are selling out at the speed of light these days. I am not exaggerating when I say if you see something you love, take action immediately before it’s gone! 

And as you are filling your requirements for your comfy, luxurious, and chic travel looks, be sure to keep in mind that these also make incredible holiday gifting ideas!

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