Packing for a mid-winter beach vacation

With my son in Havana.

If you are fortunate enough to afford a trip somewhere warm when it’s freezing at home, you’re faced with a dilemma. That is, if you enjoy dressing well: what to pack?

I believe that dressing well matters. I also believe that you don’t pick and choose when it matters. If I care enough about myself and my surroundings to dress well in the city, why not the beach? Don’t the people down there deserve as much respect as the people up here?

Enjoying a typical Cuban morning ritual: local cigar and coffee.

Like hundreds of thousands of other Canadians, my family often goes to Cuba in the winter. And I am always disappointed by my fellow travellers who look like they’ve come to mow the lawn. Don’t get me wrong, I don’t expect everyone to be wearing a suit on the beach. But must you really wear your flip flops, oversize tshirt and loud print shorts on the airplane?

As Bryan Lowder says so eloquently his article about dressing well for travel, “Just because we may be anonymous does not mean we are invisible.” What we wear communicates to those around us, no matter where we are. And once you are at your destination it is worth putting in a bit of effort as well, I would argue, if only to show the locals that not all Canadians are eyesores.

Smoking a cigar on the farm the tobacco was grown.

I will admit, however, that dressing well on vacation is complicated. It’s hard enough to dress well in the summer when there are fewer fashion choices (no vests, overcoats or gloves). Add to that having to pack and take care of your wardrobe on the go, and it gets trickier. (Try it with a little kid and you’re playing on ‘advanced’ level.) So here are a few of my vacation outfits that can be mixed and matched on winter getaways:

The flight

Linen suit, linen/cotton shirt, knit tie, panama hat, woven belt, loafers with light socks

The trick about flying south is that you are leaving a very cold climate for a very hot one. So I try to compromise: I’ll be a bit cold when I leave, and a bit warm when I arrive. But I’ll be spending most of my time in an air-conditioned airplane, so I really dress for that. And nothing beats linen for warm weather wear. While it is not the same as wearing nothing, it is the most comfortable fabric I’ve found. Its ability to wick away perspiration means you won’t feel stifled in the heat. But it does mean your clothes need to be washed more often. Oh, and that concern about linen wrinkling? Embrace it. There is an elegant nonchalance about wrinkled linen that for me says “I’m on vacation.”

Where I got it: This suit was custom made by Walter Beauchamp Tailors, shirt by Suitsupply, tie from The Knottery, hat from Aborigen Handcrafts, belt found on eBay, loafers from Allen Edmonds (found on eBay) and socks from Grreat Stuff

On the town

Linen sport jacket, oxford cotton shirt, linen/cotton pants, woven belt, panama hat, boat shoes

Once you’re down south, chances are you’ll visit a town or city. If it’s cool enough, I wear a linen jacket because, you know, I’m a grown man. But I have been known to forgo the jacket when it’s simply too hot. In that case, a good quality, well fitting linen or cotton shirt – long sleeve – is my go to. Since I wear hats for both form and function, a panama is essential. It keeps the sun off my face and neck while also looking dashing. But I’ll be honest: wearing a hat on a hot day, no matter how light-weight, will heat up your head. But guess what? So will direct sunlight. When it comes to shoes, I never wear open toe because, in my opinion, men’s feet are not attractive. My casual summer solution is boat shoes. They were designed to be worn without socks, so they are cool and comfortable on hot days. Plus, being leather and a classic style, they add just that bit of refinement to an otherwise casual outfit.

Where I got it: Linen jacket by Ibiza (found on eBay), shirt and pants from Brooks Brothers, boat shoes from L.L.Bean

On the beach

Polo shirt, linen pants, panama hat, espadrilles

Polo shirt, linen pants, panama hat, woven belt, espadrilles

A well fitting polo shirt is a thing of beauty. It can be at once casual and elegant. The polo, unfortunately, suffered greatly in the 90s with drop shoulders and very loose fits. That, and the fact that sales people at most discount electronic shops wear them, has relegated most polos to joke territory. But if you apply the same rigour to choosing your polo that you do to the rest of your wardrobe – excellent fit in the shoulders and waist, high quality fabric and construction – it is an essential summer shirt. At the other end of my outfit, since I forgo open-toe sandals, I choose espadrilles. This light, Spanish shoe is tailor made for the beach, looking at once relaxed and classically elegant.

Where I got it: Shirt by Brooks Brothers, pants by Mexx, espadrilles by Espadrilles.ca

In the water

Board shorts

No, I do not wear an old-timey one-piece woollen bathing suit. Although I’d love to. In fact, the desire to still look elegant and grown up while swimming has presented the greatest challenge for a mid-winter vacation. A lot of men’s swimwear is sporty, bulky or unflattering, especially for those of us with mature figures. For many years I simply gave up and wore a pair of bright orange draw string shorts that pinched me at the waist and ballooned out around my legs. But this year after much, much searching, I found my solution (thanks in no small part to Put This On): board shorts. Originally for surfboarders, you can now find board shorts that look essentially like well-cut kakhis, with pockets, zippers and a snap waistband . They are made of a nylon mix fabric that dries quickly and include an internal drawstring for extra support. Best thing is, these shorts look so good I’m happy to wear them around the beach, even into town.

Where I got it: Shorts by Onia (found at Winners)