55 Winter Travel Outfits That Look A-Plus Upon Arrival

112 Shares
STYLECASTER | Winter Travel Outfit Ideas
55 Start slideshow
Photo: STYLECASTER/Getty Images

December tends to be a whirlwind, and no matter what your background and which holiday (if any) you celebrate, most of us find ourselves with some time off on our hands around this time of year. This typically means visits to family and friends, often out of town, or maybe even a vacation with your S.O. (in which case, please bear these travel tips in mind).

MORE: The Hidden Health and Beauty Benefits of Mistletoe

While traveling, comfort is key, but of course, you also want to look chic AF when you arrive at your destination—especially if it’s somewhere exciting, or to see people you don’t get to visit often. We suggest opting for loose (yet cute) knits, leggings, wrap jackets, sneakers, and boots. We love the idea of rocking a silk PJ set with sneakers and a cool puffer jacket. Throw on a scarf, beanie (because who has time to do their hair?) and you’re ready to to jet.

Ahead, we rallied 55 winter travel street style pics and a few of our favorite cozy pieces you can splurge on if you’re in the mood to treat yourself for that extra-long flight to wherever you’re headed for New Year’s. Happy traveling!

0 Thoughts?
1 of 55
STYLECASTER | 55 Winter Travel Outfits
Blush Pink & Yellow
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Blue Babe
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
The Pullover

Pullover, $475; at Daniel Patrick

STYLECASTER | 55 Winter Travel Outfits
Camo Clan
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Creeper Shoe Crew
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Velvet Puffer

Moncler Puffer, $1,295; at Neiman Marcus

STYLECASTER | 55 Winter Travel Outfits
New York, New York
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Scarf Pop
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Shades of Olive
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Classic Sneaks

The Royale sneaker, $169; at Greats

STYLECASTER | 55 Winter Travel Outfits
Sparkle Sparkle
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
The Brown Puffer
STYLECASTER | 55 Winter Travel Outfits
Lady in Red
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Jersey Jumper

Dress, $79; at COS

STYLECASTER | 55 Winter Travel Outfits
Cozy Casual
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Printed All Over
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Athleisure Shirt

Shirt, $348; at Sleepy Jones

STYLECASTER | 55 Winter Travel Outfits
Atleisure Pants

Pants, $348; at Sleepy Jones

STYLECASTER | 55 Winter Travel Outfits
Red Meets Orange
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Faux Fur Collar

Coast, $138.60 (was $198); at Guess

STYLECASTER | 55 Winter Travel Outfits
Teddy Bear Coat
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Faux Leather Leggings

Leggings, $110; at Spanx

STYLECASTER | 55 Winter Travel Outfits
Baby Blues
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Business Casual
STYLECASTER | 55 Winter Travel Outfits
Oversized Hoodie

Hoodie, $78; at Tobi

STYLECASTER | 55 Winter Travel Outfits
Quilted Cutie
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Striped Cardi

Cardi, $129; at Sanctuary

STYLECASTER | 55 Winter Travel Outfits
Steal His Look
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Hint of Rose

Valentina boots, $595; at Taryn Rose

STYLECASTER | 55 Winter Travel Outfits
Leather Statement
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Tied with a Bow

Allyn Pant, $295; at Ramy Brook

STYLECASTER | 55 Winter Travel Outfits
Green Team
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Leather Pants
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Alpaca Handknit Sweater

Edun Sweater, $790; at Vreela

STYLECASTER | 55 Winter Travel Outfits
The Sleeveless Puffer
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Distressed Denim
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Boots with the Fur

Marc Fisher boots, $149.97 (was $249.95); at Nordstrom

STYLECASTER | 55 Winter Travel Outfits
Old School
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
2-in-1 Jacket

The Ajin, $1,995; at Nobis

STYLECASTER | 55 Winter Travel Outfits
Tomboy Chic
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Wrap Trench

Trenc, $1,600; at Zimmermann

STYLECASTER | 55 Winter Travel Outfits
Military Green Things
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Striped

Leggings, $15 (was $39.95); at American Eagle

STYLECASTER | 55 Winter Travel Outfits
Blue Pop
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Patched Up

Boots, $179; at L.L. Bean

STYLECASTER | 55 Winter Travel Outfits
Ankle Details
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Green Puffer

Michael Michael Kors, $169.90 (was $258); at Nordstrom

STYLECASTER | 55 Winter Travel Outfits
Off-the-Shoulder
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Oversized Sweater

Sweater, $700; at Cienne New York

STYLECASTER | 55 Winter Travel Outfits
Stripes & Motos
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Casual Bomber
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Circle Marks the Spot

Sneakers, $359; at THEY New York

STYLECASTER | 55 Winter Travel Outfits
Classic White Tee
Photo: Getty Images
STYLECASTER | 55 Winter Travel Outfits
Knitted Sweater

Sweater, $41.23 (was $58.90); at Torrid

STYLECASTER | 55 Winter Travel Outfits
Classic Black Puffer
Photo: Getty Images

Next slideshow starts in 10s

Holiday Looks That Won't Expire on January 1st

Holiday Looks That Won't
Expire on January 1st
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits
  • STYLECASTER | 55 Winter Travel Outfits

Promoted Stories

share