Hillary Chybinski: What to Wear When You Travel

Wednesday, March 09, 2016

What to Wear When You Travel

Welcome to another weekly fashion post, where I share real fashion for real women. Each week, I highlight at least one outfit that I'm wearing right now, as well as provide ideas and inspiration to help you get dressed in the mornings. Life is hard, getting dressed shouldn't be. This week we're going to talk about what to wear when you travel.

Shirt - Ann Taylor | Tank - Aventura Clothing | Leggings - Hue | Boots - Bandolino

No matter where you are going, or how you are traveling there, comfort is key. No one wants to arrive looking like a rumpled, wrinkled mess - right? So whether you are driving, taking the train or flying, you want to pick pieces that are comfortable as well as good looking. As with so many other outfit dilemmas, layers are a solid answer.

If you have time to change or don't have immediate plans upon arrival, there is nothing wrong with pulling out your athleisure wear for your trip. But if you need to hit the ground running, you may want to wear something a little more "pulled together".

On a recent trip to NYC, I wanted to pack light, so my travel outfit needed to double as my out to dinner outfit. I chose some classic pieces and maximized comfort with stretchy fabrics. A great pair of boots and a chic poncho finished off the look. Layers, comfort and style for the win. Even after a long ride, after a little freshening up, I felt good as new and enjoyed a great dinner out with good friends.
Bag - Kate Spade | Poncho - Ralph Lauren | Necklace - Tiffany

Are you old enough to remember the days when people got "dressed up" to travel? When I was about 12, we went to Disney World, and I remember that I wanted to wear a blazer on the plane, just like my mom. Since the start of commercial air travel, men and women have dressed up in suits and dresses. Remember Pan Am? Of course those were the days before security lines and tiny seats.

These days, jeans and yoga pants fill many of the seats on trains, buses and airplanes. Occasionally there's a business suit, and very rarely a dress. Last year, I saw a sharply dressed "older woman." Even though she had on jeans and a white shirt, she had them styled so great with leopard accessories - she looked fabulous.

So some necessary fashion items for traveling:
  • Comfortable shoes
  • Sweater, Jacket or Wrap
  • Convenient bag for ID, water, etc.
What is your must have travel wardrobe staple?

catch you soon -
This post is linked up at The Pleated Poppy and at Jo-Lynne Shane - be sure to check them out for even more outfit ideas and inspiration.


  1. The whole outfit looks great. I love the blouse- doesn't look stiff or uncomfortable. And that bag? LOVE it!