36 Stylish Items You Won't Regret Wearing on the Plane

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Planning your travel outfit is often just as hard as packing. If you're smart, you'll layer the most essential pieces you've got, the ones that will keep you cozy on the plane but will also come in handy on your trip. Keeping style in mind, we searched for the type of ribbed jumpsuits and jersey sweatshirts that are live-in but standout stylish. Accessorize with flat shoes that you can slip on and off, a cap to secure your hair in place, and a carry-on tote to pack the little things. In an outfit this comfortable, you'll forget how good you look and wonder why everyone's staring while you go through security.

Madewell Jean Jacket

Madewell Jean Jacket

Would you ever go anywhere without this Madewell Jean Jacket ($118)?

Body Rags Clothing Co. Instafamous Baseball Cap

Body Rags Clothing Co. Instafamous Baseball Cap

Don't worry about perfecting your hair — just throw on the Body Rags Clothing Co. Instafamous Baseball Cap ($29).

R|Label Maxi Dress

R|Label Maxi Dress

This breezy R|Label maxi ($155) is comfy for lounging on the plane, layered up with a scarf, sweater, or jacket, and still looks chic when you land at your final destination.

Topshop Duster Coat

Topshop Duster Coat

You'll never want to shed your layers when you're wearing the Topshop Duster Coat ($55, originally $110).

Fenty x Puma Rihanna Slides

Fenty x Puma Rihanna Slides

Find a slide that's neutral, standout, and sturdy too. The Fenty x Puma Rihanna Slides ($90) are a sure bet.

Sub Urban Riot Tee

Sub Urban Riot Tee

This Sub Urban Riot Tee ($34) will look cool later on thrown over a swimsuit on the beach.

Sandro Star Motif Jacket

Sandro Star Motif Jacket

Wear your leather moto with the most personality. We love the stars on this Sandro Star Motif Jacket ($485, originally $610).

Coach Bandit Bag

Coach Bandit Bag

Pack all the essentials into the Coach Bandit Bag ($695).

Levi's Blue Wedgie Fit Jeans

Levi's Blue Wedgie Fit Jeans

Look for a trusty pair of jeans that give you some room to move, like the Levi's Blue Wedgie Fit Jeans ($62, originally $140).

Dolce & Gabbana Silk Banano Print Pajama Top

Dolce & Gabbana Silk Banano Print Pajama Top

Invest in something luxe and comfortable that can become a bikini cover-up later on, like the Dolce & Gabbana Silk Banano Print Pajama Top ($899, originally $1,499).

Chloé Merino Wool and Cashmere Poncho

Chloé Merino Wool and Cashmere Poncho

Never worry about the AC being turned up too high in the Chloé Merino Wool and Cashmere Poncho ($675, originally $1,350).

DKNY Ribbed Cotton Jersey Midi

DKNY Ribbed Cotton Jersey Midi

A stretchy ribbed skirt like the DKNY Ribbed Cotton Jersey Midi ($125, originally $250) is definitely ideal.

Calvin Klein Logo Sweatshirt

Calvin Klein Logo Sweatshirt

This Calvin Klein Logo Sweatshirt ($40, originally $60) is the type you can wear anywhere with anything.

Alexander Wang x Adidas Originals Run Sock Sneakers

Alexander Wang x Adidas Originals Run Sock Sneakers

Keep your foot looking stylish and feeling supported in the Alexander Wang x Adidas Originals Run Sock Sneakers ($268, originally $316).

Urban Outfitters Soft Acid Wash Blanket Scarf

Urban Outfitters Soft Acid Wash Blanket Scarf

No matter the season, you'll never regret wrapping the Urban Outfitters Soft Acid Wash Blanket Scarf ($20, originally $34) around your neck.

Cooperative Emilia Linen Button-Down Dress

Cooperative Emilia Linen Button-Down Dress

The Cooperative Emilia Linen Button-Down Dress ($79) can be mixed and matched with anything in your suitcase.

Anthropologie Sleep Mask

Anthropologie Sleep Mask

You'd be crazy to forget to pack this Anthropologie Sleep Mask ($45).

Zara Shirt Dress With Frill

Zara Shirt Dress With Frill

This Zara Shirt Dress With Frill ($50) is both casual and practical for a trip.

Calypso St. Barth Evsiba Striped Linen Tunic

Calypso St. Barth Evsiba Striped Linen Tunic

The Calypso St. Barth Evsiba Striped Linen Tunic ($110, originally $275) would make any gal feel like she's going on vacation.

Artesano Clasico Wide Brim Hat

Artesano Clasico Wide Brim Hat

Whether you're headed to a new city or a tropical destination, this Artesano Clasico Wide Brim Hat ($230) will come in handy.

J.Crew Skinny Italian Scarf

J.Crew Skinny Italian Scarf

Add this cute J.Crew Skinny Italian Scarf ($25, originally $40) to your look.

ASOS Jersey Jumpsuit With Tape Detail

ASOS Jersey Jumpsuit With Tape Detail

Stand out but stay low-key in the ASOS Jersey Jumpsuit With Tape Detail ($51).

Soft Joie Lidelle Linen Blouse

Soft Joie Lidelle Linen Blouse

What type of bottom can't you pair the Soft Joie Lidelle Linen Blouse ($85, originally $188) with?

Mara Hoffman Peasant Dress

Mara Hoffman Peasant Dress

The Mara Hoffman Peasant Dress ($257, originally $395) is perfect for pairing with a swimsuit or with wedges for dinner — and, of course, it's easy to wear on the plane.

The Row Bea Cashmere Slippers

The Row Bea Cashmere Slippers

These The Row Bea Cashmere Slippers ($591, originally $985) will never let you down.

Re/Done x Hanes 1950s Boxy Crop Tee

Re/Done x Hanes 1950s Boxy Crop Tee

Make sure you've got your favorite white tee handy. We recommend the live-in Re/Done x Hanes 1950s Boxy Crop Tee ($78).

R13 Boyfriend Top

R13 Boyfriend Top

Make sure your striped tee is extra slouchy and comfortable. Try the R13 Boyfriend Top ($195).

Sam Edelman Carrin Platform Espadrille Sandals

Sam Edelman Carrin Platform Espadrille Sandals

The Sam Edelman Carrin Platform Espadrille Sandals ($63, originally $90) will match with anything in your wardrobe.

Missoni Striped Ribbed Pants

Missoni Striped Ribbed Pants

The Missoni Striped Ribbed Pants ($1,425) will lend your look extra flash.

Zara Turban Style Headband

Zara Turban Style Headband

Throw your hair in this Zara Turban Style Headband ($13), then wear it again later on the beach or with denim and a white tee.