What to Pack for a Stylish Trip to Tokyo, Milan, Dubai

July 17th, 2014

Part of growing the Articles of Style brand involves quite a bit of travel. I manage photo shoots in NYC and LA, I’m producing some new RTW garments in Toronto, and I try to attend as many Fashion Weeks around the world as possible. We’re also thinking about investing in a “Articles of Style RV” so we can travel around the country expanding our profile series and documenting the style in various cultural hubs.

With all this of travel, you think I would have a good rewards card to earn some free trips. Well, after plenty of research and advice from experts like ThePointsGuy, I’ve finally signed up for my first rewards card. The Venture Card by Capital One allows me to earn double miles (two per dollar) for every purchase I make and the miles can be redeemed against any travel related purchases. So whether I’m taking a taxi in NYC, an Uber in LA, a streetcar in Toronto, or renting a Vespa in Italy, I can simply use the points I accumulate to erase any travel-related charges from my bill. No blackout dates, no foreign transaction fees, no airline loyalty, no hoops to jump through at all.

In the spirit of my new travel rewards, I present the second part of our “What to Pack for the Menswear Capitals” series. In the first edition I broke down my carry-ons for NYC, Paris and London. This time we’re hitting Tokyo, Milan and Dubai.

Keep in mind this is not necessarily meant as a “packing guide” for everyone to follow. These are items from my personal wardrobe that I would pack for visiting these menswear hotspots. Think of it as travel inspiration rather than a packing checklist.

Here’s 10 essential pieces to give you an idea of how I get down in these different cultural locales, considering the local style, climate, and culture.



Tokyo, in my opinion, is all about rugged workwear but in a slightly eclectic way. The Japanese break-in their menswear with the best of them, and they have a true appreciation for classic Americana. Think beat-up denim, thick canvas, and vintage chore coats. You can add a punch of funky retro pattern in there too, if you like. Oh yeah, and don’t be afraid of a wide leg or a roomier fit – the flow goes strong in Japan.

Clockwise from Top Left:

1. Vintage paint-splattered “shop coat”

2. Vintage brown felt porkpie/bucket hat

3. Knit blazer with suede elbow patches

4. Red “neckerchief”

5. Beige waffle henley

6. Leather slip-on espadrilles

7. Washed plaid shirt

8. Rugged cap-toe work boots

9. Wide-leg canvas workwear pants

10. Vintage washed jeans



Milan is about as sharply tailored as a city gets. And we’re not talking about conservative tailoring. We’re talking about bright gelato colored suits and blazers, cut to the bone. If there is a place to go extra slim and extra colorful, it’s Milan. In keeping with Italian traditions, I usually pack some stronger collars and some beefier 7-fold ties. It’s also one of the only places that I only pack tailored clothes…even my casual walking shoes are alligator drivers. Luxury European menswear at its finest.

Clockwise from Top Left…

1. Hopsack blazer with windowpane pattern

2. High collar sky blue dress shirt

3. Silk/cotton patterned v-neck sweater

4. Off-white straw panama hat

5. Orange cotton suit

6. Brown leather/suede monkstrap loafers

7. Linen glenplaid shirt w/ contrast collar

8. 7-fold silk power tie

9. Herringbone linen trousers

10. Alligator embossed driving mocs



Dubai is super HOT. It’s desert climate, although you’ll probably find yourself poolside at a very shiny and swanky hotel. I suggest keeping it extra lightweight and cool. You can’t wear too much white. Make sure to pack a trim set of swim trunks and a tank top, but otherwise keep it “new money rich” with deep necklines and super flowy fabrics. Also don’t forget a hat to keep the sun out of your face.

Clockwise from Top Left…

1. Navy/white candy stripe short-sleeve shirt

2. Sky blue striped polo shirt

3. Vintage Panama hat

4. Trim-cut swim trunks

5. White linen suit

6. Tailored chambray shorts

7. Linen/cotton floral shirt

8. Leather gladiator sandals

9. Grey tri-blend tank top

10. Custom genuine alligator loafers

Thanks of reading. I hope this gives you some inspiration to get out and travel this summer! There is no better way to learn, about yourself and about others, than experiencing foreign cultures first-hand. But don’t be on the sidelines taking pictures, get in the game! You can start by wearing the right jersey.

Yours in style,

Dan Trepanier


Shop Custom Menswear Made in America


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  • Sean

    I did Tokyo last week. My style consisted of a ton of Uniqlo to lessen the Gaijin effect…

  • James Wong

    I love tokyo, everyone is so sharply dressed! I even saw a elderly man in a three piece suit with a NY snapback on – so much swag.
    Totally agree with people in Tokyo wearing flowier and roomier trousers – as a freerunner, we wear baggy sweats as part of our style and when I was in Tokyo, I kept thinking I was seeing other freerunners when it’s just what Tokians wear casually.

  • bob

    does anyone know what kind of bag the green was is? i really like the mix of forest green and leather with a lime trim.

    • bob

      *does anyone know what brand the green bag is

  • MaleStylePro

    A well thought out selection. They are all relevant for their pertinent cities. Each city has it’s own personality.

  • Brandon

    As someone who lives in Japan, I hope Tokyo Fashion Week isn’t anywhere from June to end of September because the humidity would kill you in the first set of clothes.

  • Juan

    Awesome x 3! I’d been waiting for this since part I, and I can agree with pretty much everything you said.

    I’m from Milan, and this is actually pretty spot-on! I’ve never actually seen someone in an orange suit strolling around via Montenapoleone, but fashion-forward people over here are pretty much the most fashion-forward people you’ll ever meet.

    That Missoni sweater represents what this city is about, and I find it’s the most Milanese piece featured (along with the burgundy foulard). It’s innovative, but tailored, colorful, but tasteful, and its hues actually resemble those that you’d find in Milan most often. I’d save the full-on color look for Southern Italy or the Riviera Ligure, but you’ve painted a really accurate picture, bravo Dan!

    Also really digging the other two selections. I’ve been to my fair share of hot places (never to Dubai though), and I can certainly vouch for the sandals and the brimmed hat. Tokyo’s also tremendously stylish, though I’d just add a few prep staples (OCBD, repp tie, penny loafers) as I understand the Japanese are big on them (I have a Japanese friend who’s obsessed with Take Ivy).

    Looking forward to part III, keep up the terrific work guys!

  • John Doe

    Is Dubai really a “menswear capital”? I would think that Los Angeles, Madrid, Seoul, or Toronto would come before it.

  • John B

    The green bag in the picture is amazing! Not sure about the workwear looks (Tokyo) though, I like some aspectsof it, but I don’t think I’d be able to pull it off!

  • http://Keyboardandcompass.com/ Jeff McAllister

    I love the idea of a menswear RV, particularly for visiting those smaller North American towns that might otherwise get looked over (and, of course, a trip to BC ;).)

    Also: enjoying these kits but it would be great to see what luggage you pack each in and whether that also changes as drastically with the destination.

  • jon

    First, I support any and all menswear RV excursions.

    Second, how do you pack toiletries and undergarments? I’m always so impressed with how you can fit a long weekend (or even a full week!) in a simple bag. These essential items often can take up a lot of space that could be used for something more stylish! Thanks!

  • Todd Ruhnau

    I really like all these looks but being someone who has never been to Milan or Dubai it would be nice if you gave a short explanation of how you see each city’s style. What aspect of each city inspired you to create these outfits. Other than than they all look great! Also, I can totally see you and Alex in a Breaking Bad style RV.

  • Tom

    you forgot to bring these boots…


  • Miguel

    I like both Milan and Dubai, last of options to mix and match.

    Thank you for the article, you should do one for vacationing in hot cities.

    • cc

      dubai is one of the hottest cities on the planet

  • AFH

    I’m in a similar though bigger dilemma at the moment. I will be residing primarily in Copenhagen for a few months, with occasional trips back to Blighty. I have to essentially live out of two suitcases + whatever I can get out of H&M and Cheap Mondays – currently working out my capsule wardrobes for Summer, Autumn and Winter. Autumn and Winter aren’t so bad (jeans, boots and Fair Isle jumpers), but Summer is trickier.

  • Rams

    Dan after looking over your selections several times, I picked up more than several pointers when packing to travel in or out of the country. Culture,climate and comfort, not necessarily in that order but it is what I see in your choices. Food for thought definitely. Thanks.