I travel all over the everywhere, all the time. I am on the road about once a month. In the last two years, I have gone diving in Bonaire, hiked for five days to Machu Picchu, had a Viking feast in a cave in Iceland, and had countless dinners and cocktails all over the Carribean, South America, and beyond. One of the things I learned along the way was how vital it is to pack well. The truth is, travel is one of my first loves, but traveling is one of the worst experiences. Flying is a nightmare. The airports are crowded, the process to get through TSA is long and arduous, and the seats on airlines aren’t made for adults. The worst part of all of that is that the prices don’t reflect the hassle. This is why packing efficiently is so vital. When I went to Bellevue, Washington, it was one of the more difficult to plan for because there was such a wide range of things to do.
Checked bags are expensive, so I had to learn the life skill of overpacking without having to check a bag. Part of that learning curve was simply economic, and part of it was because I am a chronic overpacker. I love to dress up, I love to test out outdoor clothing, and I can’t help but have more costume changes than the host of the Oscars. Since I am not a gatekeeper, here are the tips that I have picked up along the way.
Planning your looks
The most important thing I will tell you about this process is probably the most obvious. Overpacking without checking any bags takes a lot of planning ahead. You will want to look over your itinerary to ensure you don’t overlook any event you will need a specific look for. When I started planning for my trip to Bellevue, I started looking into the events I had planned. Being across the water from Seattle, and having a distinct Pacific Northwest feel, Bellevue has a unique mix of urban nightlife and outdoor experiences. I am the kind of packer who likes to have a daytime outfit for whatever I have planned, and a dinner/cocktail outfit that is a little more elevated. Here are some tips for planning your outfits:
- Focus on a capsule wardrobe approach. No matter how much planning you do, things happen, so you will want most of what you pack to work together seamlessly. That means choosing versatile garments that can effortlessly transition from casual to formal wear. I needed something casual with mobility when I hopped a seaplane to fly over Lake Washington or when I walked off a mountain with a parachute strapped to my back at Poo Poo Point. And I needed elevated wear for dinner and drinks at Ascend Prime and The Lakehouse.
- You should have one outfit that you wear on the travel day. I like to wear the same thing the day I fly there and the day I fly home. As long as it isn’t an overly long flight or you don’t drop your mediocre airline meal all over it, it makes packing seamless when you can put everything in the same place there and back.
- When you start thinking of shoes, you will want to save as much space as possible. One pair for the day outfit (sneakers are a great way to go from checking out Bellevue’s downtown shopping to going on a bike ride to the shoreline or hiking through the parks) and one evening shoe (a pair of chelsea boots or versatile cap-toe is your best bet).
- Since you will be packing one of the shoes, it is best to wear the bulkiest one on the plane. Now that you will soon not have to remove your shoes at TSA, this becomes more convenient.
Packing your bags
I spent four days in Bellevue, including the day I flew there. That meant I needed four dinner outfits, and four daytime outfits (including my flying outfit). For me, an elevated dinner/cocktail look requires a jacket. Call me over-the-top if you must, but I love wearing a jacket to dinner and I rarely don’t when I travel. That means I almost always take a garment bag on my trips, and a small weekender that fits under the seat in front of me on the flight as a personal item. This maximizes the space I have to pack all of this into two bags. Don’t think you can do that? Here is how:
- First things first: roll, don’t fold. Rolling your shirts, pants, and everything in between was a trick I learned in the Army. When packing a rucksack, you want to carry as much as you can on your back so you’re always prepared. Don’t ask me to explain the physics behind why rolling your shirts and pants takes up less space than folding, I don’t know. But I do know it works.
- Ditch the hangers. In the years I have spent traveling, I have never once stayed at a hotel lacking hangers in the closet. Don’t take your own, they take up valuable space. While we’re on that subject, ditch the steamer too. At the very least, the hotel will have an iron with a steam feature. Don’t know how to use that? We’ll have to do that another day.
- Wear one of the jackets. No point in not looking fantastic on the plane, you never know who you’ll run into. And, save the space in the bag.
- All of your elevated wear can fit in the garment area of the bag, pair your trousers inside the corresponding jacket, zip it up, and now you just have to roll your casual clothing.
- Your spare shoes can sometimes fit in the garment bag, but I am a size 13, so I like to put them in the small duffel with socks and underwear stuffed inside them.
Using the right luggage
Finally, all this is pointless if you don’t use the right luggage. There is a lot of preference and objectivity when it comes to recommending products, but I have two very specific brands I like to use. The Halfday Carry On Garment Roller is the perfect size for me. I have had garment bags in the past that weren’t wide enough for my 46-long suits. Not only is this one wide enough, it also fits the three jackets I am packing perfectly. It is also roomy enough that I don’t have to worry about taking an extra weekender if I would rather take my laptop bag for work. If you’re not the kind of guy who would be in for the jackets and would rather have more room for gear, Travelpro has a selection of carry-ons and duffles that serve me well.
