It’s that time of year—you’re going away for the weekend. Whether you’re hitting the slopes, going someplace warm or just heading home—yours or hers—there’s a weekend bag in your future.
But it’s never that easy.
Let’s face it, we’ve all been there. You stuff everything in a bag, shove it all down, zip it up and head out. Then you get to your destination and what have you got? A broken razor. A toothbrush that’s full of crap from the inside of your bag. One pair of shoes that doesn’t match anything—and speaking of not matching anything, by now you’ve probably discovered you brought one stained pair of jeans and a stretched-out sweater. Did you pack in the dark?
It’s a strange truth: even the most on-trend, on-the-ball guy can get overwhelmed by packing the proverbial weekend bag. You want to keep it light and lean, but need to be prepared for anything. You’re probably in a rush. You forget the little things you need, because they’re just always right there.
But the holidays are, essentially, the weekend bag championships. This is when it really matters. You’re seeing people you never see otherwise, hitting the party circuit and maybe trying to impress her dad/sister/brother/loud uncle/ex. So pack like the stylish gentleman we know you are—you’ll thank us on Monday.
Essential #1: A good bag
It all starts with the bag. Leather is great, but it’s HEAVY. Especially if you’re traveling by train, plane or bus, hauling a leather bag can get cumbersome. Canvas is a great, lightweight choice that looks equally sleek without the extra bulk. Nylon’s another good choice. BOSS makes a bunch of great “Weekender” bags in both materials. Opt for something roomy with durable straps and at least one internal or external pocket for small stuff that’s easily lost in the shuffle.
Essential #2: Dopp kit
Shaving cream opens and gets all over your bag. Toothpaste crusts up a sweater. Deodorant comes out of the bag with pieces of lint, fuzz, hair, whatever caked on to it. Just get a dopp kit. They’re inexpensive, lightweight, easy to stuff in a weekend bag, while keeping all of your toiletries organized and together. Bonus: just grab the entire kit when you hit the shower in the morning. You’ll have the goods right there, and won’t have to worry about leaving things behind. Fill it with everything you need depending on your locale—don’t forget sunscreen for hot spots, moisturizer for colder temps—and you’re good to go.
Essential #3: Jeans
Now for the good stuff—don’t ever leave home without a pair of jeans. If you’ve got space, pack two. A dark wash is the best bet, especially if you’re only bringing one pair. They look good with everything and can mask a little spill or two. Hey, it’s the holidays after all.
Essential #4: The sweatshirt that’s not
Put down the hoodie. Drop the ripped up Michigan sweatshirt. That’s not what we’re talking about. Sweatshirts have taken shape over the last few seasons, and we love the new direction. They’re one part sweater, one part comfortable weekend sweats, creating a look that’s perfect for a low-key Sunday brunch or for traveling from destination A to B. John Varvatos has a few great choices, and so does Michael Kors.
Essential #5: The blazer
A heavy cotton blazer or linen jacket is the best choice, especially if you’re going to be carrying it in your bag all weekend. It might seem excessive, especially if you aren’t heading anywhere with a dress code, but trust us. It’s versatile and provides a nice safety net. Picture this: red wine/gravy/mustard/lipstick on your Oxford. All you’ve got is the “not sweatshirt” (see #4), a crewneck tee and a polo. Now what? Pick one. Pop a blazer on top. Return to the party, cool as ever. The blazer instantly elevates anything and has saved more than one party on our end. And for that, it’s always got a space in our weekend bag.
Essential #6: The electronics
Of course you have your iPhone. But do you have a charger? What about your Kindle? Need to update your Fantasy Football team? Don’t assume you’ll have access to a laptop where you’re going. Even if they have one—and they probably do—you can’t count on the connection being good or it not being completely commandeered by an insolent 12-year-old from sun up to sun down. If you think you’re going to need it, pack it. And don’t forget the case/charger/docking station, etc. that goes with. Worst case, it all stays in your bag for the weekend, and you’ll have a welcome diversion on the ride home.