How to Feel Comfy and Look Cute While Traveling

Catherine Cassidy (Business Heroine Magazine)
How can I FEEL comfortable yet still look stylish?

This is a common question for women.

Women who work from home, women who run errands in their downtime and ESPECIALLY for women (and men) with regard to traveling.

The frustration for those want to feel comfortable and still look cute while traveling (or even work from home) is that we do one of two things: we often overdress for travel (and our errands) and don’t feel as though we can relax in our form fitting clothes OR we are rushing around so much that we throw on any combination of comfortable items and may feel frumpy and unpolished.

 4 items you can wear for a polished, casual, and COMFORTABLE look.

(PS–these items together are also applicable to feel comfortable and look stylish for the other activities mentioned above too.)

1) Scarves add a touch of detail that otherwise may be missing.

When I talk to my clients about accessorizing, they often think I mean jewelry.

But the scarf is a prime example of an accessory that serves a few purposes:

  • It will keep you warm while you travel
  • By adding a layer to your look and something around your neckline you will feel more dressed up
  • AND you can pick a print, pattern or knit for that extra touch of detail!

Whether you are in a white button-down top, a scoop neck tee shirt or a sweater, a scarf can take your look from drab to FAB!

FUN FACT: according to Wikipedia, the scarf originated in Rome.

Also, here’s why I love scarves and their influence on your style: some women prefer infinity scarves, some pashminas, and some like shawls.

Try one, try all three. Each looks completely different and can reflect YOUR personality and style preference.

2) A cozy cardigan

Not only is this piece SUPER comfortable for travel (or lounging around the house), it’s also versatile.

You can wear it with pencil skirts and boots, belted over a dress or jeans or dress up your favorite leggings.

You may actually prefer a cozy, draped sweater. That works, too! STYLE is all about YOU, after all! But the key is that these are knits, so they’re still comfortable, even if they’re polished.

3) Have fun with FLATS.

I love shoes – especially a great heel. There is just something with how a great heel makes you walk differently. Even a cute bootie with a lower heel makes a difference!

However, when you are required to potentially spend an entire day in and out of vehicles and standing around, the next best shoe to have is a comfortable flat. Some women like ballet flats, some women like sneakers (I saw this trend quite often in Europe last year), the key is to opt for a bold color(s) or perhaps even an animal print AND to make sure your feet will feel supported. (Nothing is worse than flats that hurt more than heels!)

If you have a flat boot, then you get to have the best of both worlds! They pair great with leggings (and balance proportions) and you save the space they would have taken up in your carryon!

4) Your favorite jeans or leggings.

I typically go for jeans with a bit of lycra for extra comfort, but these can be stretchy jeans, boyfriend jeans, or straight cut jeans. Again, whatever fits YOUR style and your body type.

There is also the option of  leggings here for those who like the idea of not feeling restricted by buttons around your waist. (That would be me!)

Again, the real key to wearing jeans or leggings and feeling both COMFORTABLE and stylish is how we add the finishing touches with accessories and shoes. You don’t always have to go for the sweater, but it’s an easy way to add style AND comfort while balancing the proportion of a legging.

Now, mix+match

For instance, I love the idea of a more athletic shoe with boyfriend jeans, maybe a belt through the loops for a bit of an accent and a button down tucked in with a scarf — so it’s polished, fun and casual.

Or, if you do want to opt for leggings for a long flight, do balance with a cozy sweater that covers your rear and boots or booties. You could also go for a ballerina flat here. And, if you’re up for it, belt the sweater, at least while walking to and from the gate.

Now, which of these items do you currently have in your closet?

Chances are 3 out of 4 or perhaps all of them. Here’s what I want you to do:

  1. Pull one of each from your closet.
  2. Put them together.
  3. Take a picture see what works together, and what you like!

Hint: Being prepared and playing is what saves time in the morning when you’re rushing to get out the door AND you feel fabulous!


style is about you - Catherine Cassidy

Business Heroine Magazine


We’d love to hear from YOU…

What are your favorite ways to stay comfy and look cute while traveling? Which pieces of your wardrobe are staples when you travel? Leave your answer in the comments below! 



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