How to Pack for a Fall Weekend Trip: Style Editors Recommend Using This One Hack

IF THERE’S ONE season that makes packing a nightmare, it’s fall. The weather’s unpredictable—you could wake up to crisp, 50-degree mornings and end the day sweating through your flannel. It’s too chilly for just T-shirts but not quite cold enough for heavy coats, which means layering is key—and layers take up space. So when you’re trying to fit everything for a weekend trip into one bag, things get tricky fast.

I used to overthink packing—from my outfits and shoes down to which cologne and hat to bring. I could never make a decision because I’d like to have options on top of options, so I’d end up packing like I was leaving for a week—lugging around way too much stuff. Once when I headed up to the Catskills for a quick 72-hour getaway with some friends, I brought three pairs of boots “just in case.” Spoiler: I wore the same sneakers the entire trip. By Sunday, I was basically living out of a messy duffel bag, digging through wrinkled shirts I never even wore—and that’s when it hit me: when your trip’s only three days, packing should be a piece of cake.

Thankfully, I’ve learned how to make the most of using one bag. And if you’re struggling to figure it out, I’ve got the perfect hack for packing light on a fall weekend trip. It took a few overstuffed bags, ripped zippers and a spilled toiletry bottle to get here, but now I can pack in under thirty minutes—and actually wear everything I bring. It’s also changed how I shop for fall: I stick to versatile layers like lightweight sweaters, overshirts, and a solid pair of chinos that can handle whatever the weekend throws at me. Here’s how to do it.

Step 1: Find The Right Bag

The perfect bag is structured enough to keep your clothes from wrinkling but soft enough to cram into an overhead bin or the backseat. I used to be a backpack guy but as I’ve gotten deeper into my style, I’ve switched to sleek duffel bags—ones that can double as gym bags, take a beating, and fit three days’ worth of outfits. Brands like Monos, Calpak, and Dagne Dover make options using water-resistant nylon, recycled polyester, or coated canvas that hold shape without feeling stiff. If you’re doing the one-bag method, a matching dopp kit or tech pouch goes a long way for organization—most of these brands make mini versions that clip onto their duffels. And if you’re more of a backpack person, try Away, Lululemon, or Troubadour which make smart, clamshell-style packs that open flat like a suitcase and have compartments for shoes, tech, and toiletries.

Step 2: Pick Versatile Clothing

In general, the first rule of thumb is to bring things that can pull double duty. I used to pack full outfits—one for daytime, one for dinner, one for lounging. Now I think in layers and textures.

For fall, my go-tos are:

• One pair of dark jeans (perfect for both daytime walks or grabbing dinner-drinks at night)
  
• One chino or tech pant (travel-friendly and polished enough for casual dinners)
  
• Two tees and one henley (easy to rotate without looking like you’re wearing the same thing)
• A lightweight shacket or sweater (layers over a tee in the morning and under a jacket at night)
• A jacket or full-length coat (pick something that works anywhere; I’ve saved myself from a chilly evening and a drizzly morning)
• One pair of clean sneakers, one pair of boots (Don’t overpack shoes because they can take up too much space)
• A set of workout clothes (you might go for a run or hit the gym at least on