How to Pack for Holiday Travel Like a Pro

Photo-Illustration: by The Cut; Photos: Getty Images, Allison Bornstein

Dear Allison,

I’m traveling over the holidays and want to fit everything into my carry-on. How can I pack strategically and maximize my wardrobe?

Sincerely,
A chronic over-packer

Dear fashion friend,

I’m here to help! My credentials are that my husband and I took a three-week honeymoon trip to Italy and I packed everything I needed in a carry-on. I somehow felt like I looked cute the whole trip and had plenty of stuff to wear. I also used to travel a lot for work, so I’ve got packing efficiently down to a science. Here are my tips for packing like a pro stylist.

No matter where you’re going, how long you’ll be gone, or what you’ll be doing on the trip, the first thing you should pack is your favorite go-to outfit, the outfit you always fall back on when you don’t know what else to wear. Like jeans and a white T-shirt, for example. It’s like having a safe space in your suitcase, which is nice if travel plans go awry or you don’t feel like the best version of yourself during a trip.

I always make a mood board to avoid overpacking. I know, I know! It sounds very extra. But hear me out: When you’re looking at your whole wardrobe, it’s so easy to talk yourself into packing pieces that might make sense for the location but don’t feel like you.

The key to staying true to your personal style (and avoid looking back at photos, thinking, Who the hell is that?) is pulling images you’ve already screenshotted or saved in the past. If I’m going on a tropical vacation, I’ll go through my camera roll and find inspiration pics I saved over the summer, then create a mood board from that. I always use Las Vegas as an example: There are so many outfits that feel quintessentially Vegas but not at all right for me. If you buy something specifically for a trip, make sure it’s something you’ll wear when you get back home, too.

Lay out everything you might want to bring, then edit your selection by building different outfits and seeing what works together and what doesn’t. It seems like a lot of effort to actually try on everything you want to pack before you leave, but if you do it right, you won’t have to waste any time or energy styling yourself during the trip.

I might pull four pairs of jeans, even though I realistically only need one or two pairs for a trip. So I’ll keep the ones that match most or all of my shoes and put back the other two. If none of the shoes I want to pack look good with a pair of jeans I want to pack, I’m leaving the jeans at home.

I recommend packing a pair of silk pants, maybe even a pair with an elastic waistband. You can wear them with an oversize sweater during the day, then easily dress them up at night to make them feel more festive. Silk pants are a more practical and versatile option than, say, a red minidress or silver skirt, which should be the goal when packing efficiently. A sequined bag can also go a long way.

We have to be strategic here, and versatility is super-important. It’s okay to pack one or two wild-card pieces as long as they can be worn with at least two of your looks. If you get to your destination and only wear it once, fine. But you should never pack with that intention.

I try to save all my little jewelry bags and pack the pieces in those, that way each individual item has a home. Then I put everything in a shoe bag and carry it in whatever handbag I’m bringing on the trip so it stays nice and protected. I usually bring one pair of jeans but four pairs of earrings. I’m addicted to jewelry. Here are a few pieces I love.

Ninety-nine percent of the time, one coat is sufficient. You need a “hero coat” that works decently well with all the outfits you packed to conserve suitcase space. If you’re going somewhere like Aspen, where the coat is the look, still only pack one, just zhuzh it up with a chic scarf or hat that doesn’t take up much room. I would rather have you bring two handbags than two jackets.

My travel uniform is crepe pull-on pants, because they don’t really wrinkle (usually in black or navy so they don’t get dirty), a T-shirt, a sweater, whatever jacket or coat I’m going to wear during the trip, and then a cashmere scarf (even if it’s not cold outside, because it’s so cozy and nice to have on the plane). For shoes, I like a pair I can wear with socks while I travel but can wear without socks during the trip. My go-tos are slip-on Rothy’s, moccasins, and ballet flats.

Sorry, but my sweater is not getting that gross on the airplane, and neither is yours! Maximizing your travel wardrobe means repurposing pieces during the trip, especially if you’re only packing a carry-on. The sweater can be re-worn with other clothes in your suitcase.