How To Dress Like a Man for Travel, Not Like a Tourist

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With London, Spain, Morocco and South Africa ten days away, it’s time to prep for a month-long journey. I’m going to explain what I’m taking and why, and hopefully the gentlemen can take something away. Unfortunately, I’ve never dressed like a lady … when there was not cash involved.

Keeping in mind the weather is going to change for me from fall-like to a bit balmy and chilly at night and ending in summer temps. So this will be an all-weather wardrobe.

This is my tough-love advice for my brothers — if you dress like 13-year old boy at work, which is jeans, sneakers and whatever plaid shirt you can find that’s clean, you’re going to have to kick it up several notches. On the other end, it you are Mr. GQ smooth with the latest trends and high-end fashion, you’ll have dial it back. The key is striking a balance that mixes comfort, portability, practicality and versatility while not looking like a tourist.

Let’s start with the jackets.  Sportcoats will be your best friends. Inner pockets will keep pickpockets away from your wallet, cash and phone (when mixed with a shoulder bag). The front pockets can hold non-valuables like tissues, mints and your hands. They can be warn all-day and then blend into night-time for going on. In fashion, it’s called day-to-night.

With my two coats, I’ll bring my jean jacket if I’m going to a local pub/bar or if it’s a little more chilly. The light brown jacket is thin and unstructured so it can pack easily. My dark blue is a little more weighty, but all-cotton. I’ll wear that on the long plane trips for the arctic temperatures of the flights.

Then I’ll bring two scarves to add a little color and fit into London and Spain. The dudes love their scarves there. Remember my post about circular scarves and their multiple uses. There you go.

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With button-down shirts, you want to avoid loud colors and complex patterns. It’s all about simplicity so that you match everything with your jackets and your pants. Everything you see above are not dress shirts, but are slim fit. Europeans dress to fit their thinner frames in general.

Blue is the best color for traveling because it fits every season and can match easily with any pant and jacket. That’s why I’m bringing one dark and one light. The light chambray will be breathe easier and hold it’s shape for the whole trip.  Plus, all the sleeves can be rolled up so I don’t have to bring dorky looking short-sleeve shirts.

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What we have above starting from the left to right: light khakis cut like a slim jean, cotton-linen pants that roll-up, selvedge denim, slim stretch light cotton blue trousers and skinny black jeans.

The pants for this trip are a little tricky with all the various climates. I usually travel with a traveler’s suit I got from All Saints that I can wear together and separately. Unfortunately, it’s all wool and that’s not going to fly in Africa. So with the blue trousers and my blue coat, I have something suit-like for my Upper Class flights or a night out to a classy cocktail bar.

Uniqlo makes a lightweight pant that rolls up to the calf or the knee like a short. This will save me from bring dorky shorts. I’ll wear this for hikes up Table Mountain or a day trip to the Sahara.

The selvedge jeans is a must for your wardrobe. It’s a religion in Japan to find the right pair. They are rigid, so they will hold it’s shape and endure the beating it will take.

Add in 10 plain t-shirts, 10 undies, 10 pairs of socks, a compact rain poncho, a flat cap, swim trunks and maybe a light grey sweater, and I’m good to go. While packing, if I feel I’m packing too much, I’ll just knock out a pant and shirt.

The end result for all this — multiple outfits and uses. I can dress down and up and still be comfortable for almost every occasion and setting.  Plus, I don’t have to put much thought into what to wear and won’t feel like I’m wearing the same thing every day. I’ve done this so many times that I spent five minutes picking out the clothes for this trip.

Hopefully, fellas, you got some pointers. You can follow my guide and, as a click bait headline would say, “up your fashion game.”

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