4 Packing Tips to Get a Weekend's Worth of Stuff in One Backpack

I have a confession to make: I'm a textbook over-packer. The ugly truth: me, struggling down the subway steps with my rolling suitcase, an inappropriately warm coat tied to its handle, a "purse" which is really more of a large beach bag slung over one shoulder, a canvas tote in my hand stuffed with the 14 things I forgot to add or can't fit in the suitcase, and a recycled paper bag filled with travel snacks in the opposite hand. I'm laughing at myself just thinking about it. My back and arms, however, aren't laughing.

Help, I say. Help!

Inspired by our handmade Waxed Canvas Backpack, as rugged and handsome as Indiana Jones, I set myself the challenge of packing for an entire three-day weekend in the 13-inch by 12-inch sack. The leather-strapped pack is a natural daytripper—it perfectly fits a laptop, afternoon snacks, a long-sleeve tee, wallet, phone, and a few extras. But for purposes of this experiment, I was determined to push its limits. (Spoiler alert: It came through.)

Following four simple rules, my packing began.

1. Pack light, dress heavy. I'm a cold-blooded human and love to feel swaddled, so I couldn't let go of my favorite sweatshirt. I bought it because it's the perfect blend of sweatshirt-meets-sweater, so I can wear it with jeans and it doesn't look like I'm at a 12-year-old's slumber party. I couldn't fit it in the sack, so I wore it instead. Buses, trains, and planes tend to be chilly places anyway. The pictured maroon sneakers wouldn't fit either, so I wore them. So sue me. I was able, however, to fit a pair of flat, fancy sandals into one of the exterior pockets.

2. Know when to roll and when to fold. The tip you hear over and over when it comes to packing: "roll everything." Its omnipresence is not for naught; this one really does work. In my experience, lightweight and thin fabrics are better to roll, like my gray T-shirt, pink jersey dress, and white button-up. For thicker pieces of clothing, like jeans and sweatshirts, I like to layer them, and then fold in the sides to make a flat square. This is especially good if you're packing in a suitcase, because it can lay flat on top of everything.

3. Plan your outfits. The last thing I'd ever do is plan an outfit. I can't even make my bed in the morning. I had to set aside my scoffing and have come to accept that planning ahead is tantamount to efficient packing. It's hard for me to let go of my most stylish pieces, but no, I do not need an embroidered caftan that I might wear to afternoon drinks on a veranda that most definitely will not be happening. Opt for the basic of the basics. That means a shirt you can wear in at least two scenarios, like a nature walk and a dinner where some semblance of put-togetheredness is required. If you're of the dress-wearing persuasion, dresses are the holy grail of space-saving. And you only need one pair of pants: jeans. They go with everything.

4. Stuff things inside other things. Little pockets of space are your friends. Stuff unmentionables, phone chargers, and socks (you can never bring too many socks) inside a pair of shoes. Plus, you'll know right where to find them when there's a flash rainstorm and you need to get to your extra pair of socks quick! For toiletries, bring the bare minimum: I chose face wash and face lotion. I use our Stasher bags (you can use them over and over) to seal up the little bottles—either nabbed from hotels, bought in the travel section of a CVS, or DIYed with favorite mini bottles from Muji. And dry shampoo is a savior.

My findings: I almost fit everything! As I mentioned before, I had to wear the sweatshirt and the sneaks. I slipped my water bottle on one of the removable straps—it's more accessible that way anyway. And you might not want to put a pair of shoes in an exterior pocket, but you can and I really, really wanted to wear them, OK?

I know you've got stellar packing tips. Lay 'em on me!

Tags: The Shop, Tips & Techniques, Travel, Life Hacks, Hit the Road, Snack