How to Pack a Bag

Just got back from a trip that was supposed to be three days and turned into five. Most of it was spent in St. George Utah and then we decided to make the drive the rest of the way down to Long Beach and see some old friends.

Packing is always something that’s been a bit difficult for me. I tend to overpack and end up wasting valuable space. Even on this trip, I took my laptop when I didn’t end up using it a single time.

But there is an art to packing a bag for any length of trip. The key is to pack items that will work well with anything else in your arsenal. That way you can where the same shirt with something different and it ends up looking like an entirely new outfit. Here are the basics that I recommend.



For a four-day trip you can get away with packing four and not having it take up too much room. that being said, you can get away with even fewer if you want. I recommend something comfortable to drive or fly in like a henley or a polo. These are both still going to work if you’re going out at night when you throw a jacket on over them. I also recommend a white button-up shirt. This one saw more action than anything else I packed and still ended up looking different each day because of what else I had on. A patterned button up shirt is also great for either dressing up or down.



This is a staple I will cover in more detail shortly. An unstructured jacket is probably the best piece of clothing I own. I can wear it every day, beat the crap out of it, stuff it in my bag, and it still comes out looking great. Depending on what you wear it with, it can look dressed up or just casual cool. By day five I still had people at the Pike at Long Beach complimenting my jacket.



There’s that V-neck again. If it’s cool out and you don’t want to wear a jacket for the third day in a row, throw this on and you’ll still get your High/Low flow going without looking like you only brought one thing to wear.



Given the time of year, I didn’t see a need to pack any shorts, those can either be added in or substituted for something else. The pants you want are pretty easy. Dark, straight jeans and a pair of slim, flat-front khakis. Both of these will look good with anything else you own.



The cool thing about desert boots is that they can be used to make you look more dressed up or more dressed down. It just depends on what you want to do. Khakis, a green henley, no jacket and boots looks very casual but still very stylish. Dark jeans, a button-up shirt, a jacket with a pocket square, and boots makes you look like you’re ready for a night on the town. I’ve also found, since I don’t own driving loafers, that these boots are my favorite shoes to drive in. The boat shoes are great for being down by the pool or even going to the beach but also can be pulled off if you’re going out to dinner that night.



I prefer to go sockless as often as possible, but I always back an extra couple of pairs. They take up little-to-no space and can be great if the temperature drops below what you were anticipating.

Swim Suit


Because, even though it barely topped 70 degrees, we haven’t been able to swim all year and it was great to spend some time in and hanging around the pool. Also, we had a hot tub on our deck.



I’ve found when I travel, especially when that travel is a road trip, that I don’t get to shower at regular intervals. We ended up making the drive home from LA to Salt Lake Friday night instead of leaving Saturday morning. This means you’ll smell and your hair will start to get weird. You will look even worse after you’ve been passed out in the back of the car for three hours. A hat is a perfect solution. Throw this on and you won’t feel like an idiot when you stop to grab snacks at the gas station and your hair is sticking out on all sides.



I grabbed a casual one but you could go any direction. Just make sure it’s sturdy enough to get the job done.

Dopp Kit


It should already be packed with the supplies you need, so just throw it in.



My wife bought me these for Christmas this year. Most of the time no one but you and your lady will ever see what you sleep in, but there’s always the exception. Those of you with kids can vouch for me on this. We made this trip with my wife’s sister and her husband and I didn’t want to be walking around in my underwear or just a pair of basketball shorts. Grown-up pajamas may take some getting used to, but I don’t think I’ll ever go back.

Misc – Pocket square, pocket knife, extra cash, and a good book to read by the pool.

Take all this


Put it in this


And you’re good to go.