Travel Outfits: How to Look Chic When You’re Flying

Travel Outfits: How to Look Chic When You’re Flying

Listen—I’m all about rocking a cute travel outfit when I’m heading out of town… but I wouldn’t be caught dead wearing heels to the airport.

To be honest, I don’t even like wearing jeans on a plane (although I’ll occasionally make an exception if they’re REALLY comfortable jeans, or if my flight is under three hours.)

Usually you’ll find me rocking a head-to-toe set of my favorite affordable cashmere during the winter, and a lightweight loungewear set during the summer.

I often see pictures of bloggers at the airport posing next to their cute pink luggage wearing like…wedges and a mini-dress. HARD PASS. How is that even comfortable?

travel outfit ideas
travel outfit ideas

For this reason, I decided to put together a little guide to cute travel outfits…featuring things that you’ll actually want to travel in.

Because believe it or not, it’s possible to rock comfy loungewear, leggings, or a jumpsuit and still look SUPER chic, as long as you style them properly (especially my favorite faux leather leggings.)

Below are a handful of great travel outfits I found while trolling IG—and the exact things you can buy to replicate them.

P.S. My new other new go-to travel outfit is this chic sweat suit from Summersalt (and you can use “LINDSAY10” for $10 off.)

(Also: if you’re also on the hunt for stylish carry-on luggage…I got you covered.)


1. A Comfy Jacket

Treasure & Bond Denim Jacket

Aviator Nation Hoodie

Departure Airplane Mode Sweatshirt

2. Sweatpants

Rag & Bone Miramar Sweatpants

Free People Sweatpants

Zella Soft Pocket Joggers

Alo High Waist Sweatpants

3. A Cozy Jumpsuit

Zella Knit Romper

Bobi Sleeveless Jumpsuit

Madewell Drawstring Jumpsuit

4. White Sneakers (or Slip-On Sneakers)

APL Techloom Wave Lace-Up Running Sneakers

Tory Burch Sneakers

Dr. Scholl’s Sneakers

Veja Sneakers



Sleeveless Top | Black Joggers | White Sneakers | Duster Cardigan

Looking for more travel secrets? Check out my post about How I Use Credit Card Points to Travel for Free.


Black Top | Leggings | White Sneakers | Round Sunglasses | Leather Moto Jacket


Black Hoodie | Striped Blazer | Black Leggings | Black Sneakers | Round Sunglasses


White Pullover | White Joggers | White Sneakers | Baseball Cap | Tan Blazer