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Photograph courtesy of Nappa Dori

My boyfriend has it pretty tough packing for the holidays this year: He’s starting in NYC, taking a trip up to the frigid Finger Lakes wine region in New York, spending Christmas in Boston, visiting his mom in Orange County, then ringing in 2015 in San Francisco. That’s a whole lot of varying climates, from flip-flops weather to chilly hike-friendly temperatures to biting cold.

Luckily, most people traveling to see loved ones this season won’t have the same suitcase-packing nightmare. But even if you’re traveling 100 miles, packing a bag for the holidays can be tough.

We wanted to help make it easier, so we reached out to Kate Larramendy, the design director at Horny Toad Activewear (the brand soon to become Toad & Co. in 2015). Larramendy has had years of traveling, working with fabrics, and packing, having been the design director at the famed activewear brand, Patagonia. We figured she’d have some great tips for making the most out of the little space you have to pack, and we were right—from the one piece you need to bring, to how to keep your clothes smelling fresh through a week of travel, here are her tips.

1. The One Piece You Need to Pack
I never go anywhere without a cashmere sweater,” Larramendy says. She praises their versatility, both functionally and fashionably. “They’re warm as insulation under a coat, but light enough to wear comfortably indoors.” For men and women, a cashmere sweater can also be worn in both dressier and more casual situations. “For a woman, a cashmere sweater and a necklace pulls everything together.” She advises seeking out the best you can get, however. “You can get cashmere sweaters at many different quality levels—but I promise, if you invest in a high-quality sweater, it will serve you for years to come.”

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2. Don’t Fold Your Clothes (Really)
Larramendy is pretty anti-fold: when you don’t have ready access to an iron, those creases could be menaces to your holiday wardrobe. The solution? Roll your clothes. “Rolling clothes is the ticket for having it arrive in the condition as when you pack it,” she says. “I fold things in half, then in half, and then roll.” You’ll avoid having a huge crease, she explains, since you’ll be distributing that pressure over the surface of a garment instead of at the fold, even if you stuff your bag. For an easier fit, Larramendy recommends rolling your clothing into logs about the same size. “It’ll end up looking like a bunch of burritos.” We wish more things were described that way.

3. Consider Your Coats
Big, bulky coats and jackets take up way too much precious space in your luggage. Larramendy’s solution? “I love packing a light thermo insulation for warmth—and they’re designed to be stuffed into something. A Portland, Oregon company named Nau makes a down blazer, which is my all-time favorite travel piece,” she says. “It’s a really minimalist, lightly insulated down jacket, but the styling suggests otherwise. When I’m wearing it, I feel like I look more put-together than if I were wearing a puffy parka.” Larramendy also suggests bringing a vest and a jacket to layer or wear apart, depending on what you’re doing.

4. Pack Your Soap
This is one of our favorite pointers that Larramendy gave us: Pack a bar of fragrant soap amid your clothes in your bag. “I always keep a little bar of a favorite soap in my bag, so my clothes always smell good. Especially after a while, when you get some of your worn clothes in there.” Another perk of packing a bar? You’ve got back-up soap, just in case the place you’re staying at doesn’t have it, or you’re not a fan of the scent.

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5. Practice Makes Perfect
We’ve all been there: You want outfit options when you go on a trip, but find yourself wearing only a few pieces over and over again. “I always, after a trip, try to assess what I didn’t wear,” explains Larramendy, “And that means I didn’t need it. I always make a mental note about it, or even write it down. If you do that, after a few trips, you’ll start to get more confident about the stuff you actually need.” Larramendy recommends to keep your options simple—lots of neutrals and solids, with accessories to dress everything up.

6. Make Your Shoes Count
Shoes are another big challenge in bag-packing. While you should be super picky when it comes to bringing kicks, it doesn’t mean you can’t make the shoes you do pack work. “On the way home, I stuff dirty clothes in my shoes to make more space for the new things I’ve acquired.” Larramendy’s reasoning is that it takes up the same amount of space, but you’re capitalizing on the empty space inside the shoes. And since you’ll be getting gifts for the holidays (we hope!), you’ll probably need it. So, start stuffing.