Trunk full of clothes

Packing Tips for the Well-Dressed Gent Who knew packing could be stress-free?

So, you’re going away for a few days. Business trip, weekend getaway, or otherwise, you want to be prepared for any and all encounters that may come your way, but you don’t want to be caught lugging around several suitcases that are ultimately just going to slow you down. Packing is an art. Overpacking is not. In order to help you prep for your next weekend getaway, we’ve created a definitive list of packing tips for bringing your stylish essentials and reducing travel-induced stress without compromising on the things you need most.

Read next – What to Wear While Traveling

Table of Contents

Choose Your Weapon: The Ultimate Carry On

You have to be strategic about your packing approach. That strategy begins with selecting the most functional carry-on/weekender bag, tailored to your personal style and the airline’s carry on baggage size limits. Remember, you’re allowed one decently sized carry on bag, as well as a second, smaller personal item. You want to get optimal usage out of both when packing light.

When searching for a weekender bag, choose one with ample space (2000 cubic inches at least) and sturdy material (canvas, suede, and leather are always solid picks). With style and functionality in mind, here are some of our favorite weekender bags, all for $250 or less.

1. The Abingdon Weekender, J. Crew, $198

Navy Blue Abingdon Weekender bag by J. Crew

Why it’s great:

  • Brushed leather trim
  • Made-to-last durable construction
  • Sturdy

2. The Twill Weekender, Everlane, $95

Brown Twill Weekender by Everlane

Why it’s great:

  • Stylish
  • Great value
  • Lightweight
  • 100% water resistant


3. The Outfitter Luggage, Herschel, $129.99

Navy Blue Outfitter Luggage by Herschel

Why it’s great:

  • Built-in shoe compartment
  • Can be carried or worn as a backpack
  • Comes with a laundry bag

4. The Sotnik, Chrome Industries, $220

Black Sotnik bag by Chrome Industries

Why it’s great:

  • 100% waterproof
  • Can be carried or worn as a backpack
  • Large cargo capacity both inside and out

If you travel frequently, and can afford to splurge, this is the creme de la creme of weekenders:

5. The Garment Weekender, Hook + Albert, $445

Green Garment Weekender by Hook and Albert

Why it’s great: This weekender compacts the storage capacity of a garment bag into a carry on-approved duffel. It folds flat to store suits in its built-in garment bag and folds back up to create the walls of the bag. Keep your best suits and shoes safe and sound in this awesome, unique bag designed specifically for the dapper traveler. This weekender sells out quickly, so keep checking back on their website to score your very own.

Read next – What to Wear While Traveling

You’re aiming for ease and efficiency when it comes to quick travel. Limiting the things you pack to one carry on bag allows you to skip past the bag check and head straight through security without having to check your luggage. Maneuvering with a carry on also allows you to leave the airport immediately upon arrival, as you won’t need to wait at the baggage carousel for your belongings. All in all, learning to strategically pack a carry-on bag will save you a good amount of time that could be spent taking in the sights or taking a client out to lunch.

Packing the Essentials: It’s All About Strategy

Yes, you can fit everything you need in a weekender bag. But how?

You want to stick to clothing options that are sharp, classic, and foolproof, so they will be appropriate across a variety of scenarios. Choose simple items that are good quality and versatile. The gents at Dappered suggest choosing one group of neutral, complimentary colors and assembling a variety of items around that palate, so no matter what items you wear on your trip, they will look good together. Guaranteed.

Now, take your bag and let’s get packing:

1. Pick Your Transit Outfit

Plan to wear your heaviest and bulkiest items on the plane, train, what have you. Whether this means wearing a full suit (if the trip you’re going on requires one), or throwing on your boots, jeans, a sweater, and a thicker jacket (if you’re going somewhere cold), it’s up to you. Doing this will leave your bag lighter and free up space for other things without compromising on clothing.

2. Shoes First

Along with the shoes you plan to wear in transit, choose one other all-purpose, comfortable pair. Pack it at the bottom of your bag.

 3. Roll your Ties, and Don’t Forget the Socks

Socks rolled and stowed inside of dress shoes

Roll up your tie(s) and/or socks and pack them inside your shoes. This will keep your ties structurally safe while you fill up your bag with stuff.

4. And then Keep on Rolling

Roll up underwear, t-shirts, and any light sweaters tightly and surround your shoes at the bottom of the bag, providing a stable base for the next layer….

5. … The Suit

If you’re planning to bring a suit along, and you’re not wearing your suit on the plane, fold the jacket, pants, and button-up carefully and store in a plastic bag. For a video tutorial, check out Business Insider.

6. Top it Off

Fold denim, slacks, cashmere sweaters, and button-up shirts and lay them flat on top of your suit. Try to limit yourself to 1 or 2 of each, at most.

7. The Dopp Kit

Collection of travel sized accessories

Store travel-sized toiletries (under 3 oz for liquids) and any miscellaneous necessities in a Dopp kit. This will keep them all contained in one place.

8. Utilize Every Inch

If your bag has interior or exterior pockets, use this space for chargers, rolled-up belts, and other small essentials.

9. Prep Your Personal Item

Finally, pack your laptop, files, headphones, and any other essentials you need during the flight in your second, smaller bag. A briefcase, backpack, or messenger bag should do the trick.

Follow these guidelines, and you’ll be jet-set in no time. All you need to do now is figure out how you’ll spend all of your precious extra time.

Read next – What to Wear While Traveling

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