Thanksgiving Weekend in a Carry On

I often visit Boston for Thanksgiving weekend, and the hectic holiday airports and chilly weather always make packing a challenge. It’s easy to be overwhelmed by the thought of having to pack heavy cold-weather clothes and boots, and a holiday centered around food, lots of family, and potentially seeing old friends demands a flexible wardrobe. Here’s my foolproof packing list for a stylish Thanksgiving weekend, and best of all, it fits in a carry on!

Thanksgiving in a carry on

  • I opt for black skinny jeans or jeggings when I travel and need outfits to play double duty. They can be dressed up or casual, and offer extra stretch for those second helpings of pie. (Before you comment about only bringing one pair of pants, think about how often you re-wear pants at home. Exactly. It’s 4 days, and science says jeans never get dirty.)
  • I adore my caramel-brown Frye riding boots, and they go with absolutely everything. Wear these babies on the plane, since they’re your bulkiest item to pack.
  • Speaking of boots, I like to wear and pack wool hiking socks. They’re super warm, cozy, and wool has magical powers that keeps them from retaining moisture or odor, meaning you can slip your boots off for a post-dinner nap without having everyone flee the room.
  • Since there’s usually snow on the ground in Boston around Thanksgiving, I bring a pea coat and carry it on the plane.
  • Opt for loose knits and flowy layering tops. They look cozy casual when you add an infinity scarf, and if you slip on some heeled booties you’ll still out-style that cousin in a super-casual “oh, I just threw this on” kind of way.
  • Speaking of, pack a pair of heeled ankle booties. I love my black suede pair with a chunky heel, since they instantly dress up an outfit but still allow me to walk on icy walkways.
  • A doctor-style satchel purse is structured enough to pull your casual outfits together, but also roomy enough to hold extra plane snacks or your iPad (for when you just can’t handle entertaining your five year old cousins anymore). 
  • Adding a sheer blouse takes up minimal space, won’t wrinkle, and a chic animal print (go for small and well-done, not large tacky print) guarantees you’ll have something to wear when your high school friends want to meet up for a drink.
  • Round out your minimalist weekend wardrobe with two scarves that can double as a plane or train pillow and wrap.

When packing small for a trip, focus your clothing around a basic color scheme and try to ensure that nearly everything can be mixed and matched to avoid having one statement piece taking up precious packing space. Keeping things cozy and casual with small elements that can take it up a level also allow you to be flexible and comfortable no matter what you end up doing.


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