How to Pack Your Travel Bag Light

Overpacking is the biggest mistakes people make when they travel.


Because all that extra baggage weighs you down and impedes your journey!

Traveling light makes the trip more enjoyable, less stressful and more productive because you have less to think about, less to lose, and more time to enjoy.

That being said – how do you fit all the luggage you need for a trip into one bag?

It starts with a simple checklist to eliminate all the unnecessary items that go into your bags.

Let’s start by asking some basic questions about your trip:

What is the weather like where you’re going?

Is there a dress code that requires a suit or formal clothes?

How long are you going to be traveling?

Once you answer these basic questions, pack clothes that coordinate so you can interchange with no hassles.

Also wear your bulkiest clothes on the plane.

Before a trip I lay out all my clothes, accessories, toiletries and shoes that I want to carry with me on a table or bed. This gives me a clear idea of what’s going into my bags.

Here’s a breakdown of what I packed on a recent trip to from Wisconsin to Arizona. Keep in mind that Arizona has a milder temperature of 85?, compared to the 35? Wisconsin. So, I packed fewer jackets.

Start With Your Luggage – Choose The Smallest Bag That Still Fits Your Needs

If I’m driving by car, I pack my clothes in a garment bag. This is an easy way to protect my clothes from maple syrup stains, spilt water or milk in the back of the car. I use one by Blue Claw.

If I was looking to impress, the weekender bag from J.W. Hulme would be my choice.

However, since connecting flights require walking a mile, a bag with wheels is absolutely necessary.

For this trip, I chose the Genius pack, which is the perfect carry-on bag and is quite handy with its use of checklists.

Pocket SquareClothing To Pack When Traveling Light

On this trip, I wore a brown jacket, lightweight cashmere sweater, a dress shirt, undershirt, a smart pair of dark jeans and driving a comfortable pair of moccasins.

Let me repeat – you want to wear as much as you can on the plane to save space in your travel bag.

I make sure my jackets can be worn with all the other clothes packed for this trip. My versatile blue jacket with pocket square and business cards goes into my bag.

Now, for shirts. I packed a blue striped, solid blue with a slight herringbone pattern and a new grey check shirt from Men’s Style Lab.

A white linen shirt doubles as a dress shirt or can be worn as a casual shirt and a chambray is quite handy.

I’m also testing out a travel shirt from Libertad Apparel. You’ll see that all these shirts can be worn with any of the trouser and jacket combinations.A_2-360x1024

For pants, apart from the denims worn on the plane, I usually pack a pair of casual grey chinos and a couple of dress slacks in beige and darker brown.

For underwear, I packed three pairs  of blackStuck by Ribbed Tee boxer briefs. Along with three under shirts, classic, white, blend and lightweave, also from Ribbed Tee.

To cover my daily workout routine, I packed aTasc running shirt and my favourite shorts from Strongbody apparel. I prefer these running shorts to my swimming trunks because I like how they fit me in the legs.

I packed four pairs of socks – from mens style lab and I deliberately left out athletic socks, because I can wear the dress socks with my workout shoes.

What Shoes To Pack When Travelling Light

A pair of driving moccasins from Paul Evans are perfect for a long day of flying. They have a lot of traction, making them comfortable when walking is involved.

The other shoes I packed for this trip are the Paul Evans wingtips and double monks.

I love both of these shoes as they look great and are easy to match with the rest of my travel ensemble.

I especially love the double monks as I can slip them on and off when going through security at the airport – they are dressy enough to be worn with a suit in most situations as well.  And if I decide to leave the driving shoes at home these are my second most comfortable pair of shoes.

I also packed a pair of old running shoes to keep up with my fitness goals on the road.

 Paul Evans Driving Shoes

Accessories To Carry In Your Travel Bag

Three neckties are sufficient, a red tie with small repeating patterns (watch this video to find out why I chose this color), a dark green with polka dots and a casual knit neck tie.

Included in my bag are shirt stays that clip the bottom of my shirts to the top of my socks. This keeps my shirt tucked and in place. Also throw in a couple of handkerchiefs and my shirt collar stays.

Other essential accessory items for me are:

  • sunglasses
  • wallet
  • credit cards
  • $100+ cash
  • drivers license and/or passport
  • my military veteran card
  • 3 packs of gum
  • Neutral shoe cream and brush to polish my shoes

What Grooming Products To Carry?

Higher-end hotels stock the basics – shampoos, soaps, dental kits, shaving kits.  That being said – I always carry my own as I have particular wants from my grooming products.

That being said – the first thing I do when I check into my room is ask for a few extra emergency kits – this enables me to have extra on hand and saves time if I do need them in the future!

If you need to freshen up during connecting flights, remember to pack sample-size portions of toothpaste and mouthwash along with a toothbrush.

If you forget something, don’t worry, you can pick up hair products, laundry essentials and grooming products at your destination.

Essential Electronics To Carry On Your Trip:

A lot of this depends on your personal needs, but for me I usually carry:

  • Smartphone (iPhone & charger).
  • Laptop and charger.
  • Portable mouse.
  • Video camera, extra battery, and charger.
  • Headphones

On trips longer than I week I usually bring a digital SLR, microphone, and webcam.

maxwell-bagIn My Travel Briefcase

Depending on whether I’m taking my laptop, I choose to carry either a portfolio bag or a larger leather bag.

In the smaller bag, I carry an extra pocket square, charger, connector for iPhone, extra battery pack charger, pair of earbuds, my marine corps coin (just in case I bump into another marine in a bar) and wet wipes, for obvious reasons.

That’s a summary of what I packed on my recent trip. As I said earlier, you need to start with a checklist to help you pack your travel bag. You can use this one to start with and change it according to your travel needs:

Checklist To Pack A Travel Bag Light

(This will see you through 5-7 days of travel):

  1. Jackets: Depending on the weather, you may only need two jackets. Wear the bulkier one and pack the other one in your bag.
  2. Shirts: Three dress shirts, three semi-casual shirts.
  3. Trousers: Wear a pair of jeans and pack a couple of dress pants and a pair of chinos.
  4. Shoes: A pair of brogues and a pair of double monks for work, moccasins for the airports and a pair of running shoes for a workout.
  5. Underwear: Three pairs of underwear and undershirts.
  6. Socks: Four pairs of dress socks. I prefer not to pack my athletic socks.
  7. Sports wear: Shorts, T-shirt, swim trunks.
  8. Accessories: Watch, ties, collar stays.
  9. Grooming: A basic dopp kit with toothbrush, toothpaste. If you need to carry shampoo, soap or hair products, transfer a small quantity into a TSA-approved travel tube.
  10. Electronic: Laptop charger, phone connector, camera.
  11. Other Essentials: First Aid items, earbuds, wet wipes, cream and polish for shoes, a brush or comb, a lock.

The next time you travel, remember to pack light, pack only what you need and use this checklist or create your own.