A Moncler puffer keeps things warm and stylish. Photograph from @moncler on Instagram
Style Necessary Style

How to keep warm in style: your winter travel checklist

Because baby its cold outside.
Monchet Olives | Dec 07 2018

Winter is coming and travel options are plentiful—especially those proverbial winter wonderlands. Unless you are traveling business or first class, where its veritably bring-all-you-can, it would be good to think through what clothes to bring to keep you warm.

When my wife Margie and I went to Ulaan Bataar last winter, and it was minus 40, we had the right clothes for the weather. Or so we thought. We dressed too European and ended up looking like Russian drug lords in heavy cashmere topcoats and fashion forward scarves.  We were warm, but out of place. Mongolia is a rugged country, and apparently so is its everyday wear. Think climbing Everest.

But there was no need to fret—UB was overrun city, and a trip to the market got us chic puffer jackets and fur hats. Problem solved.

Moral of the story: destination decides style. But these are some of the key decisions you need to make without going for the Uniqlo marshmallow look.

@thenorthface on Instagram

Winter for Filipinos is the time we deck ourselves out and feel the Christmas spirit. For most, Boracay is far from their list of holiday destinations: the colder, and more manageable the budget, the better. Over the years, Tokyo, Whistler, Hokkaido, and Helsinki have replaced Seoul and Paris as options.

Travel has become easier than ever. There are just so many strikingly beautiful destinations during the colder months. We opted for Ulaan Baatar over a more temperate Madrid. Niseko was on the to-do list a few years back, but travelling for hours on end can make one really take to editing their packing list with more seriousness.  

Smart packing is always key.  Do your research to see just how low temperatures could drop, and if you’re sensitive to cold, bring a big, warm coat instead of trying to layer yourself into immobility. You can always tuck it into the overhead bin if you don’t want to wear it on the plane. Believe it or not, it's possible to pack a heavy winter jacket. Harder when in coach, though.

A pair of dark sneakers will look good, but won’t be as useful in a wintry mix. If there’s even a chance of chilled precipitation where you’re headed, invest in sturdy, Northface-type waterproof boots with traction. It helps—I have slipped on the ice and it can be scary. Warm, dry feet can also spell the difference between a fun, active day and one that’s reduced to the time you spend as a sad, human-shaped ice cube.

Yes, winter boots tend to be bulky—even the stylish ones. Suggestion: try the vibram soles at Santoni. They are admittedly a pain to take off at airport security, but don't let that deter you. Boot removal amounts to no more than a cumulative 15 minutes of your trip, says Travel + Leisure, accounting for the pulling-off and the putting-back-on of very complicated boots. And without which you’ll be spending hours on end braving the elements. If you do decide to pack a pair, stuff them full of smaller items to save room.

@camerlengo_official on Instagram

In addition to the essential winter accessories (gloves, scarves, hat), consider picking up the HeatTech tights, shirts, and undies from Uniqlo. They are the best in the market and are thin and easy to wash in the hotel bathroom. And since they are thin, it is easy to move in them. Use a cross body bag and keep it in your coat.

The best way to wear all of these essentials without entering Marshmallow Man from Ghostbusters territory? Coordinate your outerwear, and keep the base layers basic with neutral sweaters, easy-to-layer tops in heat-retaining fabrics. And stick to dark denims.

Here are my essential pieces for travelling in style. Again I caution you, if you decide to do Norway, etc., you will need expedition wear, and that’s a whole new ball game.

OVERCOAT OR PUFFER? It’s a matter of choice. Honestly, I’d rather layer it right, and wear a more elegant cashmere or woolen overcoat. Keep it classy. More importantly, it’s perfect for that Instagram moment. Plaid and herringbone are very on-trend now, and are available at Zara or H&M.

@goodmans on Instagram

EYEWEAR. Winter glare is real, so take on mirrorized shades.

GLOVES. Leather or HeatTech or both. The cold may be too much so you may need to invest in gloves that will turn your hands into Mickey Mouse digits. Buy heat packs in the pharmacy. They are like packs of nuts that you crack and place in your pocket to keep your hands warm.

THERMALS. I swear by Uniqlo. When we were in the outskirts of Ulaan Bataar the HeatTech kept my already blubberous legs cold, and after removing the jackets, I still felt comfortable. The founders of the company are right. It’s really damn good technology.

SCARVES. Pick up a few cashmere or wool scarves and play around with wearing them. When you travel, drop by the flea market or local chain and pick out a few. Remember you will be wearing much of the same things for the trip; different scarves could easily put a different spin on your look.

@successful_business_look on Instagram

PARKA. These down jackets will keep you warm and fuzzy, and are perfect for inclement weather. Puffer types are okay, but I think the expedition types with fur hoods are more appropriate. This is something you can get at North Face, Patagonia and Filson. Those that have multi-liners are better so you can layer accordingly. Want to spend a bit more? Invest in Canadian Goose Expedition or my personal favorite, Barbour.

@shuhei_nishiguchi on Instagram

BOOTS. You need shoes that will manage snow on bad days. Keep them waterproof. Bring a pair of nice loafers—be sure the sole is thick—since the cold can permeate through them immediately. And while you are it, this is the time to wear socks, unless you are the iceman.  

@castello_boutique on Instagram

LAYERS. I think the best advise I can give is to pack HeatTech layers and cashmere sweaters or turtle necks with some color. Everything for a winter trip is actually available at Uniqlo, so between checking the climate readings, and what the locals suggest you pack, you will be absolutely fine.

HAT. I guess if you must, a woolen beanie or muffs may be needed. I would eschew that for a fedora. To keep warm, just down a nice cognac.

@poloralphlauren on Instagram

As for me, we’re thinking Madrid this time, where we can dress with civility and enter a bar without peeling off layers like an onion. Given our experience in Mongolia where walking around made us feel like mascots, I would opt for a fashionable winter spot where you can walk, enjoy, and not worry that your runny nose will become a stalagmite.