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


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