Last time around, Donna offered winter wear advice for women. This time, it’s your turn, fellas.
Overshoes vs. boots
In preparation for this article, I have been checking out men’s footwear as I wonder downtown for the past couple of weeks. The number one thing I have noticed is how many of you are wearing your good dress shoes in the snow. Why? You are going to ruin your favourite shoes by spring, and possibly end up on the client side of things: as a plaintiff in a slip and fall!
Instead, check out the many sleek boots for sale that you could be wearing, like this pair by Cole Haan ($248 [Ed. Note: No longer available], available at Zappos.com). Leave your dress shoes at the office to change into, or throw them in your litigator bag to take to court (I have never met a courtroom that did not have a place to stash my boots somewhere out of the judge’s sight). I will repeat my advice from my last edition that I gave to the ladies: if the pair of boots you find lack grip, you can have a cobbler add this for about $10.
I understand overshoes are a traditional way to keep one’s feet dry; however, I (along with most other women) do not understand why you would want to walk the streets in rubber shoes. However, if you insist, at least opt for a pair in black or brown. I recently spotted an otherwise well dressed gentleman downtown (nice suit and overcoat) with neon overshoes.
To hat or not to hat
Another thing I have noticed is how few gentlemen are wearing hats these days, even in minus double digits. Aren’t you cold? If you are worried you’ll look silly in a hat, don’t be. A classic wool toque is universally flattering. If you find that option boring, do not 
be afraid to try something different. There are a variety of winter hats styles out there that are a little less common, even though they are traditional. For example, you could wear a wool fedora, like this one ($42.99 [Ed. Note: No longer available], Banana Republic) or a driving cap, like this one ($34.99 [Ed. Note: No longer available], also Banana Republic).
Get under an overcoat
A wool overcoat is even more essential for male lawyers than female. Finding one that suits you is a pretty straightforward exercise. First pick a colour that suits your wardrobe — I find charcoal grey is the easiest to mix with most men’s wardrobes.
Next, go for the highest quality you can find within your budget. The most important thing to keep in mind is cost per wear. For example, if you buy a $500 overcoat that you are not thrilled about and only wear it to get through this winter, you may have been better off with that $1,000 overcoat you love that gets you through two winters (cost per winter = $500), and it would be an absolute steal compared to that cheaper coat if it gets you through three winters (cost per winter = $333).
Boxing day sales and beyond are the best time to find a new winter coat. No need to brave the crowds, there will be lots of sales online as well.
Warmth is in the details
Last but not least: do not forget to add a scarf in your favourite colour and some leather gloves (incidentally, either of these make a great gift for men or women). Here is an article with some good tips on how to tie a scarf.
Donna Wilson is a Toronto-based commercial litigator at Affleck Greene McMurtry LLP. Her style and beauty column will appear every second Wednesday.
Photo by Alan Cleaver