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.
Don't worry about perfecting your hair — just throw on the Body Rags Clothing Co. Instafamous Baseball Cap ($29).
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.
You'll never want to shed your layers when you're wearing the Topshop Duster Coat ($55, originally $110).
Find a slide that's neutral, standout, and sturdy too. The Fenty x Puma Rihanna Slides ($90) are a sure bet.
This Sub Urban Riot Tee ($34) will look cool later on thrown over a swimsuit on the beach.
Wear your leather moto with the most personality. We love the stars on this Sandro Star Motif Jacket ($485, originally $610).
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).
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).
Never worry about the AC being turned up too high in the Chloé Merino Wool and Cashmere Poncho ($675, originally $1,350).
A stretchy ribbed skirt like the DKNY Ribbed Cotton Jersey Midi ($125, originally $250) is definitely ideal.
These Madeleine Thompson Eshon Striped Cashmere Track Pants ($142, originally $355) are cozy enough to get some shut-eye in.
Look sophisticated and well-prepared for your travels in the Tory Burch Robin Pinstripe Cotton-Blend Seersucker Culottes ($295).
This Calvin Klein Logo Sweatshirt ($40, originally $60) is the type you can wear anywhere with anything.
Keep your foot looking stylish and feeling supported in the Alexander Wang x Adidas Originals Run Sock Sneakers ($268, originally $316).
No matter the season, you'll never regret wrapping the Urban Outfitters Soft Acid Wash Blanket Scarf ($20, originally $34) around your neck.
The Cooperative Emilia Linen Button-Down Dress ($79) can be mixed and matched with anything in your suitcase.
Use this Barney's New York bag ($89, originally $180) as both your carry-on and beach bag.
This Zara Shirt Dress With Frill ($50) is both casual and practical for a trip.
The Calypso St. Barth Evsiba Striped Linen Tunic ($110, originally $275) would make any gal feel like she's going on vacation.
Whether you're headed to a new city or a tropical destination, this Artesano Clasico Wide Brim Hat ($230) will come in handy.
Add this cute J.Crew Skinny Italian Scarf ($25, originally $40) to your look.
Stand out but stay low-key in the ASOS Jersey Jumpsuit With Tape Detail ($51).
What type of bottom can't you pair the Soft Joie Lidelle Linen Blouse ($85, originally $188) with?
This Emerson Thorpe Elma Silk Bomber Jacket ($183, originally $365) was made for layering.
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.
These The Row Bea Cashmere Slippers ($591, originally $985) will never let you down.
Make sure you've got your favorite white tee handy. We recommend the live-in Re/Done x Hanes 1950s Boxy Crop Tee ($78).
Make sure your striped tee is extra slouchy and comfortable. Try the R13 Boyfriend Top ($195).
The Sam Edelman Carrin Platform Espadrille Sandals ($63, originally $90) will match with anything in your wardrobe.
The Missoni Striped Ribbed Pants ($1,425) will lend your look extra flash.
The Vetements x Reebok Long Hockey Socks ($155) are stylish, and they go for miles.
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.