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Mens Fashion Guide – Staying Warm and Stylish at 20 Below


I tend to get into debates when am out and about town on the subject of my style succumbing to the harsh reality of the Canadian winter. Well, am here to tell you how you can be stylish during winter without relegating comfort to the back seat.

Winter shouldn’t be an excuse to look scruffy; it’s that season of the year that allows you to combine all those items you have collected throughout the previous season and turn them into a new and interesting look. It would be utterly naïve to underestimate the extremity of the winter conditions in Canada, but I believe you can achieve that elusive equilibrium and strike a fine balance of comfort and style.  So how do you do this?

Stylish Layering

Naturally, when the temperature begins to drop, we all layer up to keep warm. It is ‘obligatory’ and not optional, so why don’t you use that opportunity to harness the beauty of structured layering by making an effort to inject a bit of style into your layers. Fashion bloggers emphasize how layering is an “art”. While I appreciate it requires some thoughts and creativity, layering is not quantum physics! You should use this season to bring out the creativity in you.

layering 9  layering 32One vital rule of layering  you should always bear in mind is that no matter how cold it is outside, there will undoubtedly come a time when it becomes too warm for your layers (when you are inside), so your visible items should look good individually and as an ensemble. Personally, I find it easier to wear multiple thin layers than one or two chunky items that way you won’t worry too much about ruining your fitted silhouette and you could insert a flash of color in one of your inner layers to make your outfit look more interesting.

Since your inner layers such as vest and T-shirts are often hidden, they can be old and battered as long as they keep you warm. I’m a fan of the turtle neck under shirts- they are warm and tend to complete a progressive look. However, remember to keep this a neutral color as oppose to bright bold color

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You shirt layer should be light, this will provide a good visual anchor, and give a good contrast with the layer above them. Don’t be too cautious, go ahead and insert a few gingham or striped shirts in your layers, but avoid wearing two items of the same patterns. It doesn’t look clever!

The middle layer is often your sweater and cardigan, which eventually becomes your top layer when you are indoors. The fit is important, they should fit comfortably over a shirt and a vest. I prefer the V-neck jumper especially when I am wearing a tie, but crew neck jumpers are equally practical and stylish too. You could make them a statement piece by wearing a slightly bright color sweater, but make sure your pant or jacket isn’t bright too.

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Your outer layer is your blazer/sport jacket, coat, or both depending on how freezing it is. Your jacket/blazer game should be seasonal:  these are expected to be wool, tweed, herringbone, or corduroy. They should be loose enough to fit all your layers, long enough to cover them, and most importantly they should have a good fitting because ultimately they make the foreground of your outfit when you are outside.

As for coats, you should invest in a proper coat made out of wool. The style of coat comes down to personal preference, but I am of the opinion that double breasted over coats and duffle coats are timeless and practical for almost every occasion. They can be easily integrated with formal and casual outfits.

As a tip, double breasted overcoat are generally suited to tall men with a muscular (triangle) frame, short men are better opting for the slimline single breasted overcoat.

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Scarves – Draped, long, and blousy as they may be, scarves are sometimes as focal as your shirt or tie, so give this some thoughts. Don’t get too hung up on colors, go ahead and opt for bright colors if you like.

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Gloves – Although the tendency would be to reach for the trusted and functional ski and workmen gloves to keep your hands warm, lumpy and bulgy hands are not one of the hallmarks of a stylish man. There are varieties of stylish on-trend leather and knitted gloves out there. Leather gloves tend to be less bulky than their knitted counterparts, but knitted gloves are also versatile and they now come in different style and cuts. You should opt for sleek and sharp shaped gloves that are functional and versatile.

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Hat – Depending on how cold it is, you can rock either the beanie, bobble, duckbill (my favorite), or trilby on your outfit. Beanies are often perceived as being too casual, but they can be worn with formal outfit too. Although, I would recommend dark colored ones such as navy, burgundy, or grey. I particularly like Burton’s bone cobra and Nixon’s regain beanies, which you could pick up for less than $30 from If you would like to know a bit more about beanies, then check out Maygen’s recent insightful article on The history of Beanies.

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Ties – Every man needs a few dark colored ties for winter. If you haven’t got one, go grab yourself a pair of solid knitted ties in brown and burgundy colors. Ties don’t only make a simple outfit look great and stylish, they also keep you warm.


Layering in style is easy and worthwhile. The great Leonardo da Vinci once said “simplicity is the ultimate form of sophistication”. Keep it simple and don’t try too hard, but don’t limit yourself go ahead and venture into territory of seemingly unlikely combinations. You will be amazed at how a little mixing and matching can make your outfit look dynamic.  For example take a moment to picture these:

  • A camel cable sweater over a white oxford shirt with a knitted navy tie and a navy jacket or coat; check
  • A light blue shirt with a burgundy tie over a navy sweater and a herringbone grey sport jacket or double breasted overcoat; check
  • A gingham navy shirt with a brown tie and a navy sweater layered under a tweed brown plaid blazer; check

I reckon you should try one of these for your upcoming Christmas party, I most certainly will.

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Images courtesy of:

Fashion tag.wordpress. (AW 2013-2014 London and Paris fashion week)


Izi Amani