Women know all too well the significance of a good pair of shoes. Unlike shirts and pants (and very much like a designer watch) a good pair of shoes will never go out of style. High-quality footwear is the foundation of fashion — and health — and all designers and fashion mongers regularly exclaim that style starts from the ground up.

Yet, even those precious few men who give attention to their appearance rarely give a second thought to what they put on their feet. While they may be the farthest from the line of sight, your shoes are often the first clothing item others notice, and improper footwear can absolutely demolish an otherwise impeccable outfit.

If you are taking your first strides in the fashion world, here’s what to look for when beginning your shoe shopping adventure.

The Right Size and Fit

Many men wouldn’t bat an eye at the idea of leaving a store with the wrong-sized shoe simply because the shop was out of their size. More than a third of men are currently walking around in shoes that aren’t properly fitted to their feet, which not only looks odd and impacts the comfort of the footwear, but can actually deform their delicate foot and toe bones, leading to problems later in life.

There isn’t a single number that defines what size shoe you should look for. Likely, you’ll find that your foot requires a different “size” in different styles of footwear, including dress, athletic, and everyday wear.

Plus, your foot almost never stops growing and changing; you should get your foot measured at least once every year to understand exactly what kind of fit you need.

Here is how you will find the absolute best fit:

1) Shop at the end of the day, when your feet are more swollen

2) Wear the same socks you’ll wear with the shoe

3) Make sure there is only a half-inch of space between your toe and the front of the shoe

4) Don’t expect a shoe to “break in” or change after use

A Style for Every Occasion

There is an appalling trend nowadays that has men wearing casual shoes (sneakers, boat shoes, moccasins, and the like) during the most formal occasions. According to standards of men’s fashion, this is utterly inappropriate; it is akin to a woman wearing flip flops with an evening gown!

Your outfit’s bottoms determine what footwear is appropriate, and there is a particular style that goes with each length and style of pant.

Shorts. Shorts, the most casual of bottoms, allow one to wear the most casual footwear as well. Sneakers, espadrilles, boat shoes, and plimsolls are the go to shoe for any outfit with a pant above the knee.

Jeans. Still casual but able to be dressed up for more formal occasions, jeans can pair with slightly less casual footwear such as moccasins, classic high-top sneakers, and bucks.

Casual chinos. Chinos are some of the most fashion-forward pants men can wear on the street, and they match with casual yet trendy shoes like classic sneakers, moccasins, penny loafers, and chukka boots.

Dress trousers. For work occasions, you want your footwear to be professional. Shoes like wingtips, Long Wings, Monkstraps, and Bluchers pair nicely and create an appearance of professionalism.

Suits. Formal parties and important business attire calls for the most decorous shoes. This includes wholecuts and cap or perforated toe bals.

Expense and Quality

There is a well-regarded rule that you should never skimp when buying items that separate you from the ground. This includes your house’s flooring, your mattress, and, or course, your shoes. When it comes to footwear, you always get what you pay for, and the cheaper you buy, the more you end up paying down the line.

1) Designer Shoes

Designer shoes are made to be timeless in style, comfortable in fit, and nearly everlasting in durability. Of course, designer shoes tend to cost much more initially, but you should consider the expense you’ll save by purchasing a single pair of shoes that will last for years, as opposed to dozens of pairs that will fall apart in months.

2) U.S. Made Shoes

Usually, U.S.-made shoes are higher quality than those shipped halfway around the world; if you can find a local cobbler to craft particular styles of shoe — specifically your dress and business shoes — you are likely to be happy with your footwear for tens of years. However, second-best are trustworthy shoe brands crafted in Italy or the U.K.

In Conclusion

A man’s guide to buying shoes is fairly straightforward. Buy once and buy quality. Be sure that you buy shoes that are appropriate to your lifestyle and go well with the outfits that you typically wear.

The price of a respectable pair of shoes is nothing compared to a life of aching, uncomfortable feet and mismatched outfits. You deserve shoes that fit well and look fabulous with each and every outfit you love to wear.


  1. Interesting article Sean. An interesting follow-up article can be on how to take care of those pricey shoes once purchased. A good and expensive pair of shoes, with the adequate care can see its useful life be expanded by several years.

  2. It has been quite a long time since I last bought shoes, and was wondering if there was anything that I didn’t know. It’s interesting that you should actually wear the socks that you would be wearing out in public in those shoes. It would be nice to see if the socks make the shoes less comfortable.


Please enter your comment!
Please enter your name here