Before I begin, I must preface this column with a rather inconsequential and common confession: Like Sex in the City’s chief protagonist, Carrie, I have a weakness for shoes. And while this weakness hasn’t reached Marcosian proportions—strictly due to lack of funds, I’m sure—it has, at times, impaired my judgment, causing unnecessary stress on both my front hall and my account balance. That said, how many pairs of shoes should a man own? What kinds of kicks are compulsory? Do we really need to buy the whole Adidas Gazelle Vintage City line, or drop three bills on a pair of diamond and dollar-sign print Ice Cream’s? Is it possible to be fashionable in a pair of Crocs (NO!)?

Having learned over the years to trust the opinion of the opposite sex over buddies’ “those are cool” comments when it comes to what actually truly looks good, I commenced my research over wine with my girlfriend, who is well aware of my weakness, and her friend. “A good pair of running shoes is super important,” offered the friend, “so are skate shoes, flip flops for summer, a nice pair of black dress shoes and.. umm.. any kind of specialized shoes, like boxing shoes. Those are sexy.”

Now before you run out and pick up a pair of boxing shoes despite your inability to box, read between the lines with me for a moment. What the friend is getting at here is that shoes matter. The shoes you wear say something about you. And that’s important, to girls, employers, clients, inlaws, and therefore should also be important to you. According to Pam Sarlas, owner of Soul Shoes and Accessories, this awareness is key. “Seeing a man in bad shoes is a huge turnoff,” she explains. “It’s just wrong on every level. So a guy needs to make sure that whether he owns four or 40 pairs, they’re of high quality and fashionable.

In terms of the number of shoes a guy should have? Let’s just say that a fashion conscious man can be just as bad as a woman. It really just depends on the guy.” Whether you’re a minimalist or an all out shoe whore, here are three to look for when assembling your arsenal.

DRESS SHOES

Owning a good pair of dress shoes is important. If you have a job, have to attend a wedding or funeral, attend church or like nightclubs, it’s imperative. When buying, leather is not an option, but rather a must…except for the sole. If you can afford it, be my guest. You won’t regret it. But with our unruly winters, there is nothing wrong with rubber. If you can only afford one pair, go with a black lace-up boot, as it can be worn with both a suit and jeans.

If you have a little more scratch to spare, playaround with colour (brown, oxblood, etc.) and style (cap toe, oxford, loafers, etc.). Treatment spray and shoe polish are both non-negotiable.

RUNNING SHOES

According to Cheryll Oland, co-owner of City Park Runners, when it comes to purchasing a good pair of running shoes, knowing your gait (basically the way you walk) is essential. In fact, it will determine what you end up wearing. “It’s not about how the shoes look, but rather how they feel,” she explains. “Having the proper shoes ensures that you don’t damage your joints when you train.” So, take the advice they hand out in La Senza: make sure that what you buy gives you the support you need.

CASUAL SHOES

Of all the categories, this is where you get to show a little personality. Like a little flash? Go with L.A.M.B. slip-ons, retro Adidas or a pair of zebra skin Circa’s. Conservative? Ben Sherman, PUMA or a classic pair of Chuck Converse’s should do the trick. Just remember that these kicks should look good with jeans, cords, shorts and possibly a pair of dress pants. “Winnipeg is pretty skate driven when it comes to casual shoes,” offers Sarlas, “which is cool, but my suggestion is to stay away from the chunky soles and go with something a little more low-profile and European, maybe with an innerelastic system, because that’s what we’re seeing a lot of right now.” As for everything else, I’ll let you be the judge. Don’t just buy; buy well. And whatever you do, keep those damn Crocs in the garden.