man carrying leather duffle bag

What to Pack for a Weekend Trip We've got it down to a science

Packing for a work trip is easy, and if you travel enough, you probably have it down to a science. Suit. Pajamas. Toothbrush. It’s basically second nature by now. But when it comes to Vegas with your boys or a romantic getaway with your girlfriend, your weekend may require a different uniform than your standard suit. You don’t want to be that guy, packing a full-size suitcase for two nights away, but you also can’t wear the same t-shirt three days in a row. Take a look at this comprehensive packing guide to make sure you have everything you need.

Table of Contents

Pick A Bag

First off, it’s time to upgrade the duffel bag you used back when you ran track in high school. The bag you choose should be on the smaller side since you won’t be gone for long. You’ll also probably be using it more frequently, so be sure it’s built to last and has a timeless look.



Filson Ripstop Nylon Backpack Surplus Green One Size

  • Top-loading main compartment with adjustable buckle closure.
  • Drawcord-cinch top closure with storm flap.
  • Dedicated laptop compartment.

If you’re really a minimalist, you can probably fit all of your weekender essentials in a backpack. There’s no reason to break out your hiking pack that can fit 20 pounds of supplies. Instead, look for a rucksack where your stuff is easily accessible and doesn’t have too much bulk. A suitcase-style zipper is an added bonus that’ll make unpacking even easier once you get to your destination.


Weekend Trip; Holdall Bag
Satchel & Page

If you’re focused on looks and longevity, a holdall is the way to go. Focus on durability and a classic shape in neutral tones, like brown or navy. This is a timeless piece that you own for decades, and if you really want to go all out, we recommend something leather. A comfortable shoulder strap is also a must for this piece. It should also be small enough to carry onto the airplane or fit easily in the trunk of your car.


Weekend Trip; Hard-shell Suitcase

DELSEY Paris Helium Aero Hardside Expandable Luggage with Spinner Wheels, Blue Cobalt, Checked-Medium 25 Inch

  • Lightweight and Durable
  • Double Spinner Wheels
  • Deluxe Interior

One of the biggest advantages to the suitcase is mobility since wheels make it easier to move quickly through an airport. This also provides more space than a backpack would, so if you tend to overpack, (aren’t we’re all guilty of this?) the extra space gives you some wiggle room. A hard-shell option looks cool and also ensures any valuables in your bag are well protected in travel.

A Gentleman’s Packing List

Weekend Trip; Packing List

When you finally get around to choosing what you’re going to pack, paring down your wardrobe to 3 or 4 outfits can seem impossible. The key here is versatility and layering with the clothing you choose to pack. Nothing’s worse than the “just in case” jacket you haphazardly shove into your bag and don’t wear once. As a general rule, one pair of pants for every three shirts will leave you with enough options. Keep pieces in the same color family as well to make building outfits even easier.

This basic packing list will keep your bag light and ensembles cohesive. Scale the fabrics up and down, depending on what climate you’re traveling to. Heavier flannels and wool are great for a ski trip, while linens and cotton weaves are best if you’re heading to a tropical locale.


  • Lightweight sports coat
  • Oxford button down
  • Two v-neck t-shirts


  • Dark wash denim
  • Chino shorts


  • Brown dress shoes
  • White sneakers


  • Underwear
  • Socks
  • Brown belt


  • Simple watch
  • Sunglasses

That’s it. That’s all you need, clothing-wise. It seems tempting to pack more, but trust us, this is more than enough to dress yourself for the three days you’re away from the rest of your wardrobe. Pair the sports coat, button down, and dark jeans for a nice dinner out and the v-neck and chino shorts for a casual Sunday morning stroll.

Save Space

Weekend Trip; Packed Bag

Pants and t-shirts can all be rolled and placed at the bottom of your bag to avoid creases while saving space. Place shoes near the bottom of your bag as well to pack your bag as efficiently as possible with your heavier items at the bottom. Your button down and sports coat should be folded and placed on top to keep wrinkles at bay.

If you’re traveling to a colder climate, wear your all too necessary jacket on travel days to avoid taking up space in your bag. Traveling in layers may be a bit of a pain, but it’s worth it for the extra room in your bag.

Don’t forget to use your shoes to stuff socks and other small items that you don’t want floating around your bag. The collar of your button down can also be used to store your belt to stop it from being squashed in transit. Little space savers such as these can really add up.

Toss on Top

Weekend Trip; Dopp Kit

Now that the bulk of your bag is packed, make sure you remember the little things that’ll make you sigh with exasperation when you realize you’ve left it at home. Toss your Dopp kit (with only your daily products and medications!) and any electronic chargers onto the top of your bag. An extra linen bag to keep your dirty clothes separate from your clean ones can’t hurt either. 

With all this in mind, packing for your next three-day trip will be a breeze. Keep it simple and don’t let packing take away from the trip itself.

Whatever your next adventure is, don’t forget to send us a postcard.

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