Packing Checklist For The Office and Outdoors

Limited Space For Business Traveler

For a number of us, being on the road for work is a fact of life. I am not immune to this as it seems that I’ve been living out of my carry-on luggage for the last two years. During that time, I’ve been able to refine my packing list so that I can enjoy up to five days on the road, more if my hotel has laundry facilities.

Dress Code For The Office And The Outdoors

My wardrobe over the last few years can be simply described as “Office and Trail Ready“; Meaning that the style fits in my work environment as business casual but can handle the trail or anything outdoor related as soon as the work day is over. So here’s what I’ve been packing for typical five day business trip where I have to take a plane and/or car rental to another major city.

Number Of Item
2Shoes, sandals, boots, sneakers
2 or 3Pants
1 or 2Shorts
3 or 4Shirts
1 or 2T-shirts
1 or 2 Sweater, hoodie, jacket
3Pairs of socks
1Ballcap or other hat
3 or 4Pairs of underwear
1Toiletry kit (meds, toothbrush/paste, shaving, deodorant)
1Gadget kit (charging cables, headphones, wall adapater)

Travel Day

A travel day is pretty straight forward; this is a combination of comfort and no metal so that I can breeze through airport screening or do a long drive.

Footwear (1)

Depending on the time of year, this varies. But these are my go-to items for footwear depending on the season to choose from. If I’m not wearing a pair of sneakers, they are in the carry-on.

  • Keen Sandals: Traveling in the summer? A pair of these is a must.
  • Sneakers: Nothing beats a good pair of sneakers when you have to pace across the airport terminal when you get delayed for a few hours.
  • Chelsea Boots: They are a bit more popular these days, but my 7-year-old pair of Bludstones while not as pretty; don’t trigger any airport screening machine. Perfect for colder weather traveling.

Bottom (1)

I once heard a comedian who was on a plane every few days that their outfit of choice when flying was to simply sweat pants and other loose clothing. And I must admit that is true.

My preference over time has been loose, breathable and stretchy. Again, this varies during the season but I tend to wear for bottoms:

  • Pants: My travel day pants of choice have been these Showdown Chino from Under Armour. Stretchy and light.
  • Shorts: Kuhl Ambush Short is a good choice when the weather is warm. The extra pockets are great when you got small stuff for the plane like headphones, boarding passes, etc..

Top (1) & Outer Layer (1)

When traveling the main thing is to be in comfortable clothes that you can wear on those short walks from the airport parking to the terminal or taxi to the hotel.

  • Short-Sleeved Shirt: I tend to pick something soft and stylish since I don’t expect to be working out on this day. Kuhl Bravado Casual Shirt is a nice option. Another good option would be the polo shirts from Johnston & Murphy.
  • Hoodie: Nice soft and comfortable option if you expect to be inside an airport or in a rental.
  • Zip Jacket: When it gets colder and you don’t want to pack a winter jacket; I found that the Carhartt Hooded Front-zipped sweatshirt is about the best thing you can have from November to April.

Accessories (4)

  • Darn Tuff Socks: They are not cheap but these socks are worth every penny if you prefer medium weight wool socks.
  • Ballcap: pick your favorite or grab one from the kiosk at the airport.
  • Belt: A nice leather belt or one of those new webbing ones. Either way, you will probably need to remove it when going to an airport, so lets put this one in the carry-on bag.
  • Gym Clothes: You probably should add in stuff for the hotel gym just in case. Usually shorts and t-shirt

Workday Rotation

Now that you are at your hotel or Airbnb, you need to dress for Monday to Thursday with the last day being a half-day and the return trip is back home. You might only have time for a quick session at the hotel gym, or have an evening or two to hit a local park or outdoor recreation area. Either way, your time is short and you want to have the right clothes.

I’ll be omitting outerwear for colder months, but assume April to October weather along the East Coast.

Bottom (2)

I’m a long-time Kuhl pant owner and for the last two years, I’ve been rotating between Kuhl pants while on the road. The durability and styling fit in well at the office where I want to wear something nicer looking than blue jeans but seems like it was made to be in the woods. The added benefit when Kuhl pants are just starting to look worn, you can retire them from the office and keep them as weekend pants for additional years.

Kuhl Ryder Pant: Love these pants. A heavier weight denim pant with extra styling and movement in the knees makes this a winner as it fades and breaks in over time.

Kuhl Kanvus Jean: I picked up this jean in Kahki up when I was on the road last spring and I found the stretch properties and lightweight makes this a very, very good replacement to those Docker pants you have sitting on your drawer.

Footwear (1)

Red Wing Heritage Boots: While my Bludstones up above may be the logical choice for many reasons, I’ve found that it is not that great when walking along rugged trails. Depending on the location and travel day footwear option – Red Wing Roughneck 2942 Copper boots are my current favorite. These moc styled boots look great and the aggressive tread grippy lug tread gives me a lot of support during the day but also can grind out 5k walking trails after work or in the snow walking back to the hotel.

Tops (4)

This is where I mix things up. I tend to bring pieces that can be used if I have meetings or more casual as I get towards the end of the week.

  • Cotton Long-Sleeved Button Shirts: I tend to rotate between something casual from The North Face or if I want to be more business-like I head over to Johnston & Murphy.
  • Short-Sleeved Button Shirts: Not surprisingly that since I was such a big fan of their pants, that some of their shirts would come into play. What I like about the Kuhl shirts is that they have consistent color patterns, they are light and dries quickly, perfect for camp but look in place around a meeting table provided that you bring along the campfire smell with you into the meeting room ;).
  • Polo Shirt: For the last day at the worksite, this is an option.

The Color Swatch

And that will fit in a standard carry-on during a typical work trip. What do you think? Of course, this is skewed towards men and casual workplace, but depending on your job, you might be looking for new brands to explore hopefully I gave you some ideas.

Thanks to Kuhl for providing support to produce this post. All opinions expressed in this post are based on my personal view.