Sorry, But These Airport Outfits Always Make Me Cringe

As someone who travels a good bit and has a tendency to observe what people are wearing (hey, that's my job!), I think it's safe to say I have opinions when it comes to airport outfits. I'm extremely careful when choosing my airport outfits, as they have to check so many boxes and serve so many purposes, so the topic of what not to wear is something I've put quite a lot of thought into.

I do think there's a happy medium when it comes to airport attire. Obviously, most people wouldn't dream of wearing some of the getups (e.g., miniskirts, crop tops, high heels, etc.) that celebrities wear to the airport, but I, for one, typically steer clear of outfits that could pass as pajamas. There are a few especially cringeworthy outfits that I repeatedly see in terminals. Read on to find out what they are and to get the lowdown what to wear instead.

Cringeworthy: Short Dress + Sandals

Wear Instead: Midi Dress + Ballet Flats


(Image credit: Chinchilla/Bauer-Griffin/GC Images)

Exposing a ton of skin is never a good idea at the airport, so choose pieces with a little more coverage, even when it's hot outside.

On Kate Bosworth: HVN dress; Stella McCartney bag; Tabitha Simmons Ines Flats ($352)

Key pieces:

Cringeworthy: Tight, Non-Stretch Jeans + Heels

Wear Instead: Loose Jeans + Sneakers


(Image credit: Marc Piasecki/GC Images)

I've learned the hard way that tight 100% cotton jeans are a big mistake, and heels will only do you harm when running to catch a connection. Opt for loose jeans and sneakers instead.

On Bella Hadid: Mandkhai sweater; Dior belt; Miss Sixty x Elizabeth Sucler jeans; Fendi tote; Balenciaga sneakers

Cringeworthy: Tank Top + Tight Skirt

Wear Instead: Sweater + Trousers


(Image credit: Splash News)

The hallmark of a successful airport outfit? You can move freely in it, but it still looks polished. Do yourself a favor and avoid tight pieces that restrict your movement.

WHO: Cindy Bruna

Cringeworthy: Crop Top + Short Shorts

Wear Instead: Trench + T-Shirt + Jeans


(Image credit: Niceguy/Bauer-Griffin/GC Images)

Again, exposing vast amounts of skin will leave you cold and feeling grimy on a dirty plane. Instead, choose comfortable pieces that provide more coverage.

On Sienna Miller: Wrangler jeans; Proenza Schouler bag; Prada boots

Key Pieces:

Cringeworthy: Jacket + Jumpsuit

Wear Instead: Sweatshirt + Leggings


(Image credit: Niceguy/Bauer-Griffin/GC Images)

While comfortable, logistically, a jumpsuit tends to be a regrettable choice when dashing to the restroom during a tight connection. Alternatively, sleek leggings and a sweatshirt will never get in your way.

On Rita Ora: Roara Republic sweatshirt; Balenciaga sneakers

Key Pieces:

Cringeworthy: Pajamas

Wear Instead: Tracksuit


(Image credit: Bauer-Griffin/GC Images)

It's tempting to just hope that your pajamas will pass as a fashion statement, but unless you're wearing heels and accessorizing to the nines, that's probably not the case. If you want a more elevated look, try an equally comfortable tracksuit.

On Cate Blanchett: Tod's bag

Key piece:

Cringeworthy: Overaccessorized Outfits

Wear Instead: Cool Separates + Functional Accessories


(Image credit: Backgrid)

I've made the mistake of wearing too many accessories to the airport before, and I always quickly regret it. Security checkpoints are that much worse, and you'll undoubtedly get annoyed by those statement earrings midflight.

WHO: Irina Shayk and Stella Maxwell

Key Pieces:

Next, check out the items fashion girls will never stop wearing at the airport.

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.