The ultimate gentlemen's guide to packing only a carry-on

With more restrictions, both in price and size, on checked bags, packing everything into a carry-on is not only sensible but also preferable for a gentleman on the go. Not to mention, packing only a carry-on allows you to stroll off the plane and on to your destination without waiting for your bags to spin through the carousel. You can get everything you need into a carry-on with our tips and checklist.

man with suitcase

Rolling vs. folding

Believe it or not, rolling your clothing allows you to put more in the same amount of space you would folding. Additionally, by rolling your clothes, you’re less likely to have wrinkles. Another tip, roll your socks into balls and you can fit four pairs of socks into a pair of shoes (two in each shoe).

Types of fabrics

Wrinkle free fabrics are perfect for getting the most out of your carry-on packing. With the right fabrics and using the rolling method, you won’t need a hanging bag; your items will come out wrinkle free. Think silk (especially silk pajamas) for a super luxurious feel and wrinkles that shake out. Alternatively, hang clothes in the bathroom and let the steam do the trick. When picking out your clothing, try to stay in the same color theme will help with layering.

men's items


Speaking of layering, plan for mix and match outfits. Consider a casual button down shirt worn with a tie and jacket for formal business meetings and on its own for gatherings that are more casual.

Some of these items can be layered when you board the jet and used throughout your trip. Start with a lightweight shirt, something neutral and solid that goes with everything. Think sweaters that look great over button downs and on their own, or scarves that make a button down into a casual outfit. A sport coat finishes the look. Depending on the temperature of the plane and your destination, these layers can be peeled away and you’ll still look sharp. And don’t forget easy slip on shoes like loafers to make it a quick pass through security.


Pare down to only the essentials. Hotels will have shampoo, conditioner, soap and lotion. Bring your shaving needs: badger hair shaving brush, razor, cream, and aftershave (in 1oz bottles of course.) Don’t forget your deodorant, toothpaste and toothbrush.

man travel


  • 3 short or 2 long sleeve t-shirt for layering depending on climate
  • 2-3 thin silk underwear tops for layering or sleeping (these are great for even cold climates)
  • 3 button-down shirts short and long sleeve (remember you’ll be wearing a fourth)
  • 2 shorts (sub 1 pair of lightweight cargo pants if cooler climate)
  • 2 long pants
  • 1 pair dress shoes
  • 1 pair athletic shoes or sandals depending on your activities
  • Silk pajamas
  • 7 pair socks rolled into shoes
  • 7 underwear
  • 1 swimsuit (or rain jacket depending on climate)
  • 1 belt (be sure to match your shoes)
  • 1-2 ties depending on occasion
  • Toiletry bag

What are your must-have items in your carry-on?

Michael Wilkens is Founder of Wilkens.

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Comments (3)

  1. Nick says:

    Loved the article. I’ll have to try rolling clothes from now on. I recently got packing cubes but quite frankly they don’t help much. I don’t find them to compact my clothing anymore than I can do without them and the clothes get quite wrinkly.

  2. Rob says:

    This is truly an underrated skill that more people should embrace. In times like these where airlines nickel & dime you for everything, this article offers true value. Great job.

  3. Jari says:

    Don’t forget the airline rules of liquids, all toiletries can eventually be gotten at the destination.

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