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The Complete Men’s Guide to Staying Fashionable While Traveling

Dark Jeans
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The one thing I can’t stand about traveling is the wardrobe selection.

Before deciding to make travel a priority in my life, most of my money went towards designer threads, expensive colognes and new sneakers. I’m still saddened when I think of my old closet, lined with button-downs and stylish t-shirts, my dresser stacked with scents by Bulgari, Armani and Chanel. My shoe rack had the dopest kicks, with throw-back Adidas, hot new Jordan’s and  the freshest Air Max’s from that year. My ties were Italian silk and my wingtips were Italian leather.

But lugging expensive gear, which would surely get ruined, and packing all of these items into one backpack, just wasn’t going to work. When I left home on my open-ended trip to Australia, I took five pairs of shoes with me.

I was grossly over-packed.

Now, as I prepare for my trip to Southeast Asia, I’ve been forced to consider what what I need and what I don’t, and I’ve downsized from an 80L backpack (yeah, I know) to a 50L.

On top of this, as I am a traveling cocktail bartender, staying stylish is a requirement of the job. But what I’ve learned through traveling and working, is that a wide selection of garments isn’t entirely necessary. With the right pick of clothes, and the ability to mix-and-match, just a few pieces can go a long way.

Wear bright colors. And dark colors.

Your earthy tones and medium-range shades aren’t going to match well. Wear dark pants and bright-colored shirts, or bright pants and dark-colored shirts. Whichever scheme you intend to use, pick one and stick with it. Make it a theme for your entire travel wardrobe. My jeans are dark blue and my t-shirts are neon yellow, pink and white. I can essentially wear one pair of jeans with every single one of my shirts, as well as every one of my button-downs.

The outfit below is my exception, but it still sticks to the same rule. It’s simple and casual but still works!

On the Great Wall

Don’t wear t-shirts with designs

T-shirts with designs on them are less versatile and can’t be matched or used in every occasion. A casual t-shirt with a design can’t be worn to the club, and a dressy t-shirt with designs can’t be worn to the beach. A plain, bright orange shirt, though, could be worn to both. Wear that shirt to the club, with some simple accessorizing, and you’re golden. Or, wear that very same shirt to the beach with a pair of board shorts and flip-flops. That’s versatility.

(I do pack one or two of these, against my own advice, but that’s because, as a long-term traveler, sometimes I just want the comfort of wearing something more unique.)

Pack a waistcoat

This is my secret weapon. You know how girls have a little black dress (LBD) that they can wear for almost anything? The waistcoat is the men’s equivalent!

Waistcoats use very little material, so they take up very little space in your bag, plus they can be paired with button-downs or t-shirts, jeans or dress pants, and almost anything in between. A dark pair of jeans, a bright yellow t-shirt and a gray waistcoat is perfectly suitable for a night out. The simple addition of a waistcoat brings you from scrub to class with very little effort.

Wearing a waistcoat, New Year's Eve, China

Bring button-downs

T-shirts are great, but a thin, stylish button-down takes up similar space in your bag and provides a level of style that a t-shirt simply can’t. You can wear a simple button-down in the woods or in the city, with shorts or with long pants, and with either sneakers or dress shoes. You don’t need French cuffs or anything fancy. Just something with a collar. But make sure you choose something made from a thin-material. You can even get button-downs made from material that wicks sweat away, so they’re great for hiking, too!

My recommendation is to carry a few, possibly even more than t-shirts! Bring some that are plain and brightly colored and a couple with designs.

Accessorize

Most men avoid this in their daily life, but if you’re trying to stay stylish while you’re traveling, accessorizing is a must. The most important thing to note is that accessories hardly take up any space in your bag, yet they can change the entire look of your outfit.

  • If you want to dress up a little, a tie with suspenders goes a long way (don’t forget your tie clip!).
  • Keep a scarf handy (or one thick one and one thin one). Whether you’re wearing a winter-jacket, button-down or a t-shirt, a scarf can be a nice addition. Just make sure you tie it right, depending on your shirt.
  • Cool sunglasses, like a nice pair of aviators or something else that’s actually suitable to your face (that’s the most important, part, boys), can take your shorts and t-shirt combo from average to suave in one slick motion.
Rocking scarves!

Rocking scarves! Sometimes I make funny faces.

Pick your jeans wisely

Jeans are the bane of any travelers existence. They take up huge amounts of space in our bags, they don’t dry quickly, and they’re not exactly versatile for the active traveler. Yet everybody needs a pair. I couldn’t imagine my life without jeans in my bag. So pick a nice pair of jeans, and pick them wisely.

You want a pair that is well-constructed and isn’t going to break down after heavy wear, but also ones that are stylish, fit your body shape well (important!) and can pass for casual or fancy dress. I always travel with very dark blue jeans (almost black!) and they pair really well with everything else I carry.

You can also wear a pair of jeans that sport the vintage look–creased lines and faded patches. If worn properly, and paired appropriately, these can pass as almost dressy. The type of dressy that’s not dressy, but is dressy because it’s done with purpose. If your outfit is done with purpose, and it’s obvious, nobody will say a word about the fact that what you’re wearing isn’t actually dressy, and you still get to look great.

Dark Jeans

Shoes or sneakers to bring it all together

Your hiking boots aren’t going to cut it. You need to pack another pair.

Pick a pair of shoes or sneakers that go well with your jeans, shorts, shirts, and your accessories. One pair of shoes or sneakers should pass for casual or dress and you should be able to wear them almost daily.

Sometimes the easiest answer is just black or brown, but I find that blue or red sneakers always seem to work with what I wear. I’ve worn solid red New Balance’s and blue and white Nike’s, but you could also just settle with a pair of Chucks (you know, those black canvas shoes from Converse). Even those pass as hipster-dress, these days!

If you put some thought into the outfit as a whole, you’ll realize that there’s a lot you can do if only you plan it out.

I can wear my white and blue Nike’s with faded jeans, a bright orange shirt and a waistcoat on a night out, and nobody even bats an eye. The next morning, I can wear the same shirt and shoes, but lose the waistcoat and only change into shorts. It’s an entirely new outfit without changing much about what I’m wearing. And everything matches!

But, just remember, your shoes are the most important part of your outfit, so don’t overlook them. Pick something versatile and stylish, and keep them clean! Wipe them down at your hostel every night if you can, because you want to look like a respectable member of society…not the bum that you actually are!

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Want some other stylish travel gear? Check out travelFREAK’s t-shirts!

About the Author: Jeremy Foster

Born in America, Jeremy, an IT specialist by trade, packed up his belongings and left home on an open-ended trip to Australia. Years later, he's still on the move and exploring other countries. He is now a mobile cocktail bartender and the head writer for travelFREAK! You can usually find him on either side of the bar, acting wanky and pretentious about booze.

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  • http://GreenGlobalTravel.com/ Green Global Travel

    You have given this a lot of thought and while I have a more casual approach, I do very much appreciate your thoughts of clothing choice during travel as traveling light is incredibly helpful but being feeling comfortable and ready for everything from diving and trekking to clubbing and diner parties is important too!

    • http://www.travelfreak.net/ Jeremy Foster

      Absolutely! I like to stay relatively stylish when I travel and it’s actually a lot easier than people think, and there isn’t a lot of sacrifice involved.

  • Graefyl

    I never wear T-shirts with designs, you’re right, they fit in with things better. Not comfy when it’s hot and yor packing on the hard streets or a trail -I use use a heavy bush shirt fot that and it’s actually cooler. Jeans, well, what can be said….. :)

  • http://www.theshirtoffmybackpack.com Scott

    Great tips man, agree with everything. I’d also throw in a stylish hoody too as one of my absolute can’t travel without’s. Good shit.

    • http://www.travelfreak.net/ Jeremy Foster

      Great point, Scott! I always travel with a hoodie. It’s definitely a must-have!

      • http://www.theshirtoffmybackpack.com Scott

        Oh yeah, and I left for my long term trip with 6 pairs of shoes, lol. So, we’re kindred spirits there, man.

        • http://www.travelfreak.net/ Jeremy Foster

          Haha good to know I’m not the only one!

  • Susan

    Don’t tell me you got rid of the backpack I got you.

  • Mom

    Good grief. How could we have two fashionistas in the same family? Both of whom think shoes are the most important part of an outfit? I surely didn’t pass on that gene!

    • http://www.travelfreak.net/ Jeremy Foster

      Yes, you, quite obviously, didn’t pass on that gene :-P

      But we did come to that conclusion separately! There must be some truth to it!

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