Chic And Comfortable Clothes For Travel Days

Whether it’s by train, plane or automobile, travel can be equally fun and exhausting.  The allure of escaping town and exploring somewhere new is great, but being cramped up in a seat for hours on end can be uncomfortable.  That’s why it’s important to wear the right clothes on heavy travel days.  You could be too hot or too cold, bloated, chronically wrinkled, or restricted by stiff clothes.  It’d be easy enough to fix those problems with pajamas or sweats, but you don’t have to sacrifice comfort for style.  Below are my recommendations for comfy travel staples that get you to your destination in style.

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Stretchy Jeans

jeansc.jpgJeans are so versatile that they can fit any traveler’s style!  They can be dressed up or down, are super durable, and can be worn a few times before washing (great for travelers with limited suitcase space).  I usually repeat my “airplane” outfit for the outbound and inbound flights, so it’s important that I can either wash it easily in a sink or where it a couple times without feeling gross.

What’s essential with picking the right jeans for travel days though is STRETCH!  If your jeans don’t have stretch, you will be super uncomfortable sitting downs for hours on end, and bloat on the plane effects everyone (i.e. cabin pressure).

The comfiest of jeans would be jeggings, which have come a long way since their debut.  Otherwise, stretchy slim-fit jeans or stretchy boot-cut jeans depending on what shoes you decide to wear.

Jeggings / Slim-Fit / Boot-Cut


leggingsc.jpgI was never one to wear athletic clothes in the past, but after I started working out regularly, I discovered some very stylish active-wear for everyday use (since I was usually running errands after the gym).

I am prohibited from wearing any kind of Athleisure while traveling though, since most airlines only accept business casual for stand-by travelers.   However, it is a popular style of clothing for revenue passengers, and the comfiest of travel options.  You can’t go wrong with classic black leggings, but there are also some really chic options out there with some color and design.   I’d recommend understated designs and colors for leggings while traveling, and keeping the bold and daring styles for workouts.

Black / Polka Dot / Lattice

Stretchy Pants/Trousers

pantsc.jpgWhether they are chinos, slacks, or wide-leg pants, there are plenty of comfy options if you don’t want to wear jeans or leggings.  Choose something breezy like linen or cotton if you are heading somewhere tropical, so you can step off the plane and not be sweltering.  Otherwise, choose something with a medium weight twill for warmth.

If you have a really long travel day, skip out on the pure cotton and linen options, as they will wrinkle the most.

Chinos / Wide-Leg / Pixie

Shift Dress

dressc.jpgIf you love to be dressier like me, a shift dress is the way to go.  It’s forgiving with it’s loose waist-line and looks effortlessly chic.  Pair it with tights if you tend to get chilly on the plane.  I love wearing shift dresses for traveling to warm OR cold climates because I can keep the tights on for colder weather, or take them off once I hit the tropical heat.  If I choose pants to travel in, I don’t have this much leeway with changing my outfit according to the climate.  Layer them with a light jacket or sweater while traveling, especially if they are sleeveless.

Stripes / Lattice / Tunic

Relaxed Fit Tee

teesc.jpgT-shirts with a bit of drape hide bloat well and extra comfortable for long sits.  They come in luxe, soft fabrics that feel great on long travel days.  They layer great with a light jacket or sweater if you’re cold, and aren’t too hot when worn alone.  When looking for a slinky tee, keywords like “relaxed fit,” “luxe,” or “slub-knit” will help you find what you are looking for.

Knot Top / V Neck / Scoop Neck

Light Jacket/Sweater/Cardigan


Any light-weight jacket, sweater or cardigan that layers well is great to have in case you are cold while traveling.  A slouchy knit or cotton jacket work great whether you are wearing pants or a dress, and are easy to pack away.

Open-Front Sweater / Rib-Knit Sweater / Moto Jacket

Cute But Supportive Sneakers

sneakerc.jpgIf I could wear stylish sneakers for stand-by travel days, they’d be my first pick for footwear.  They tend to be the most comfortable and warmest of options, for sprints through the airport to make your connecting flight, and long sits in a chilly airplane.  They are more forgiving to sore feet since you can wear socks with them, and aren’t so tight on swollen feet.  Great traveling sneakers are light-weight, cushioned and have a bit of flare!  Choosing a pair that also works for long sight-seeing days is a plus!  I love my Cole Haan Oxford Sneakers.  They look fancy while providing tons of support!

Oxford / Metallic / Netted


Ankle Boots

bootsc.jpgSince I can’t wear sneakers while traveling stand-by, I’ve come to love my comfy and stylish ankle boots.  They are super versatile since they look great with pants or a dress, dressed up or dressed down.  Just make sure to pick a pair that have good cushion and not too high of a heel.

Black / Cognac / Taupe

Comfy Flats

flatsc.jpgFlats are equally as versatile as ankle boots and go great with everything.  There are some super comfortable and supportive flats out there, but your feet might still get cold while traveling, so I recommend having a spare pair of socks handy to slip in to.

Tan / Black / Cognac

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