Traveling Chic

Is it possible to look chic and still be comfortable while traveling?  Ok, forget possible… is it practical to try to look fashionable while traveling?  With all the taking off of shoes, belts, outer layers, and even jewelry to get through security… that alone is enough to say “forget it, I’m wearing yoga pants, flip flops and a hoodie”.  But looking (and feeling) like a schlep can be a bummer, and sometimes, needing to be presentable upon arrival means yoga pants and a hoodie just won’t cut it.  So how do you look chic, stay comfortable, and not be “that chick” peeling off layer after layer and still setting off metal detectors, holding everyone else up at security?

I started by making a conscious effort to not look sloppy.  The last few times I traveled, I made it a point to not wear jeans, sneakers, yoga pants, hoodies, or anything that made me feel like I was still in college.  I also vowed never to carry a baseball cap again.  Instead, I found some cute, fashionable hats that wouldn’t be ruined if they were stuffed info a carryon.  When I planned what I was going to wear, I made sure my outfits were easy to move in and get through security in, and that I’d be comfortable for the multiple hours I’d be sitting down.  I wore cute-but-comfortable shoes that were easy to take off for security purposes, and made sure to put a pair of flats in my bag if I was wearing anything with a heel higher than 2″.

I recently traveled for work, which is what inspired this whole post.  I figured I’d share what I wore and how it worked for me, as well as some tips.  For the way there, I had to look somewhat presentable when I arrived at my destination, but wasn’t involved in any pre-event meetings.  When I left the event I was at, I was heading straight from meetings to the airport and taking off, which also meant no jeans or casual clothes at all.  I did a lot of planning, trying on, and weighing of my options.  So how did I dress?

This is what I wore when I flew to my destination.  Not everything here is exactly when I wore, but it’s close enough to give you an idea of how the look came together.  It was way cute, and I felt like a rockstar in it, haha!  Unfortunately, I didn’t take a pic… sorry!

Overall, it was a perfect travel outfit.  The boots I have are zip-up, which could have made them a hassle for security, but I typically get to the airport early enough to not have to rush through security like a crazy.  The layers were perfect without being too bulky or cumbersone.  My carryon bag (which was actually my current everyday purse) fit everything and fit under the seat, which was great (plus it’s got a crossbody strap, which is awesome for walking thru the terminal with a latte in one hand and a carryon full of tech gear in the other!).  I definitely looked chic and put together, and was still wonderfully comfortable and able to easily control my temperature by adding or removing layers.  I ended up not changing into my moccasins, but it was nice to have them in case I decided I needed them.

This is what I wore on the way home.  Again, not exact, but close enough.  Normally, I don’t travel in dresses because I’m too cold, but I figured I’d give it a shot.  Well, ok, that and I had to be in meetings all day for work, and I felt a dress was easier to be in for meetings and travel than pretty much any of the nice pants I own (and less opt to wrinkle).  I didn’t wear the jacket during the day, but draped it over my legs during the flight.

This was another pretty good travel outfit, with the only exception being the belt, and I should have thought of it when planning.  Under normal circumstances, it probably wouldn’t have been that big of a deal to have the belt.  However, because of meetings and the timing of everything, I had about an hour and a half to get from my hotel, to the airport, through security, and onto my plane before it took off (it was either rush like crazy, or spend an extra night).  So getting through security was a bit frantic, and the belt was more of a nuisance.  I almost just stuffed it into my purse after security and ran, but was able to put it on while waiting for my laptop and work bag to get through, so it was ok.  And yes, I made my flight without issue.  I slept a little on the way home, which flattened my hair a little, so I just threw my hat on before getting off the plane and no one noticed.

Here are some tips to help you look chic while you travel.

  • Start by making a deal with yourself not to wear certain items.  If you’re big on traveling in sweatpants and Uggs, figure out suitable alternatives that aren’t as “hi I just rolled out of bed”–there are plenty of other options out there!
  • Take some time to plan your outfits out in advance and think about where you’re going after you land.  If you need to head right to a meeting or event, take that into account and make sure you wear something that not only looks nice, but stays looking nice (read: wrinkle-free).
  • Don’t be afraid to bring extra shoes.  If you don’t think you’ll be able to wear heels all day, but want to wear them later, pack ’em in your carryon bag.  Or, if you’re traveling from Chicago to Mexico in December and want to be able to quickly swap boots for sandals, stash your sandals in your carryon.  But limit yourself (hard as it may be, fellow shoeaholics) to one extra pair!
  • Definitely take temperature changes into consideration–and I don’t just mean the weather at your destination.  Take terminal and airplane temperature into consideration and make sure that you can both add a layer and remove a layer in case you get warm or chilly.  If you’re typically one who’s always cold, a scarf can be a huge help.
  • Don’t forget to try it all on ahead of time.  It sounds like a pain, but it’s important to make sure you can move in your outfit, sit comfortably in it, and that you can walk in your shoes easily and quickly (if necessary).  You can also make sure it’s easy to remove the necessary pieces for going through security.
  • Looking chic is just as much about your state of mind as it is what you’re wearing.  Try to remain calm and collected while you’re traveling, and avoid looking frazzled or frumpled.  Bring a small hair brush and elastic to tame your hair if you need to, and a travel makeup kit (powder, lipstick, and mascara should suffice) to refresh your face when you arrive.  Not only will you look chic, but you’ll feel better too.
  • If all else fails, put on a pair of big sunglasses 😉
Happy traveling!