The Traveler’s Guide to Fashion 


There are a lot of factors to account for when packing. Weather conditions, unexpected dinner parties, and everything in between can plague a packing strategy. Whether it’s a long trip or a short stay, we tend to worry about those coveted items that might just come in handy. Add the pressure of baggage size and weight restrictions, and you’ve got the ammunition for a pre-vacation meltdown.

What if you pack “resort casual” and everyone else on the cruise ship wears a suit to dinner?! It’s a nightmare we’ve all had. Luckily, it’s rarely the reality. No matter how much we stressed over what to pack and what not to pack, we make due. That being said, you really don’t want to be the guy who stands out as being improperly dressed for the duration of your holiday.

How do you avoid the seemingly inevitable packing panics? We’ve created a user-friendly guide to packing for success. Whether you’re travelling to Paris or Mexico, there are a few tips that will keep you stress-free and looking great, every time.

  1. Identify your staples. Whether your destination is arctic or tropical, make sure you have your favourite jeans, one crisp white tee, a light knit and a blazer. Those four items can carry you through 3 days of unique looks if necessary. Working around these staples will also prevent you from over-packing. It’s tempting to pack for your destination with the most likely scenario in mind, but you never know when those staples – like a blazer for an unexpected romantic date – will come in handy. On the same note, don’t fool yourself by thinking that it will always be t-shirt weather. That never happens.
  2. Comfort is key. Don’t underestimate the power of a comfortable shoe and a cozy plane outfit. Maybe you love those brand new loafers, but they don’t love you back. If you’re going to enjoy your vacation – which typically includes some sight-seeing and walking –, you’ll want your tennis shoes, too. Use the same logic when dressing for a flight: wear an outfit that will be non-irritating if you wind up sleeping in the airport after a delay.
  3. Consider your audience. Comfort might be key, but that doesn’t mean we have to see how comfortable you are. Don’t make the faux-pas of being an unfashionably sore thumb in every crowd. Friends of mine travelled through Europe with a guy who wore gigantic camouflage board shorts every day. It was embarrassing because they stood out as tourists everywhere they went. My favourite part of the travelling experience is to do as the locals do, and that can’t happen if you have a proverbial “tourist” sticker slapped to your forehead. If you’re travelling to Cuba, pack the shorts, but leave them behind on your next trip to Rome.
  4. Account for luggage issues. It’s happened to me only twice, but it’s enough to make me a paranoid traveler. I’m talking about lost and delayed luggage. My bags were delayed in London, and I wound up walking the streets in three-day-old clothes, kicking myself for overlooking my carry-on packing strategy. Put a few clothing changes in your carry-on, including the staples from tip 1 that can be re-worn and re-styled. This is usually my mantra, but the one time I didn’t stick to it, I paid the price.

The next time you travel, pay heed to this guide. Not only will you feel more secure about your choices, but you’ll look good out there, too. 


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