If The Shoe Fits…
While shoe shopping may not mean the same for a man as for a woman, it would behoove many men to spend a little more time weighing their options the next time they need to stock up on footwear. Contrary to what many people might think, there is a considerable difference between makes and styles, even if it is not always apparent to the untutored eye. The result, too often, is that men end up buying cheap, uncomfortable or overly trendy shoes when, with a little bit of extra thought, they could have spent their money on a shoe that would have lasted them happily for years. In other words, a wingtip is not a wingtip is not a wingtip.
Believe it or not, at different periods in history men’s shoes were more Carrie Bradshaw than Cary Grant. While before the French Revolution most of the world’s population was lucky to have shoes at all, European aristocrats used to flaunt their status through such ostentatious touches as floral clothing, embroidery, makeup and high heels for both men and women.
Men actually give a damn about fit. “Comfort is an enormous factor for men,” says Michael Atmore, editorial director of Footwear News. “The traditional wingtip left a lot of room and was very forgiving in terms of fit. But men’s feet tend to go up in size as they age. As such, most manufacturers don’t put a lot of effort into extreme designs for fear of limiting their customer base over fit issues.”
The question, of course, is why a man should choose to wear anything other than Rockports or sneakers. For one thing, a well-made shoe can, and should be, extremely comfortable. For another, a well-made shoe sends the rest of the world a signal about the wearer. More than any other article of clothing, shoes can influence how others view us, not to mention how we view ourselves. There’s a reason, after all, why mothers traditionally advise their daughters to first look at a man’s shoes.
General Rules for Men’s Shoes
- Try to pick a shoe that matches, or is darker than your pants.
- Although it is a safe bet, socks do not need to match your shoes. Instead, think of your socks as you would a tie – an item that can bring bring the whole outfit together.
- If wearing a belt, try to match your shoes to it, unless of course, your belt is some multi-colored striped thing.
Men’s Shoes for Jeans
You can wear almost any color or style of shoe with jeans, but avoid very shiny shoes that were obviously intended for more dressier outfits.
Boots, lug soles, sneakers, loafers and sandals all work great with jeans, so you may find it helpful to let the style of your shirt guide you.
For example – a sporty, polo shirt might work with a loafer; t-shirts go well with sneakers or retro-style shoes; long, artsy button-downs work well with sandals or mock toe oxford styles.
Men’s Shoes for Casual Pants
Whether you call them Dockers, chinos, or khakis, there are a variety of loafers, oxford and other men’s shoes that work well with casual pants.
Let the ornamentation and style of the shoe guide you towards the look you’re trying to achieve.
For example, a tassle or a buckle is a little more on the dressy side, while a woven pattern or heavy stitching is a little more on the casual side.
Men’s Shoes for Dress Pants

With dress pants, shoot for the same type of shoe that you might wear with a suit. Shinier materials usually indicate a dressier shoe, as do less bulky heels and soles. Choose a shoe that is the same color or darker than your pants, and if wearing a belt, match your shoes to it.
Color Matching for Men’s Shoes
- Black shoes work well with navy, grey or black pants.
- Brown shoes are best suited to tan, brown, beige, greens, other darker earth tones.
- Burgundy shoes work well with khaki, lighter browns, blue and grey.
- Tan shoes look great with lighter earth tones, blue, beige, lighter tan or white.
For the most part, men’s dress shoe styles run Italian, British or American. The former tend to be on the sleeker side; the second distinctly traditional; and the latter almost clunkily conservative. Of course, like so much else these days, shoes are a global product, and it’s getting harder and harder to differentiate geographical styles as well as manufacturers. For instance, Crockett & Jones, based in Northampton, Britain’s shoemaking capital, not only markets shoes under its own label but also makes them for Polo Ralph Lauren and Brooks Brothers.
Whatever the origin, a good pair of high-end men’s dress shoes usually starts around $350. As with comparing a pricey bespoke suit to an inexpensive off-the-rack number, high-end and low-end shoes are worlds apart, despite the basic similarities. Fit is the most basic difference. A well-made suit fits the wearer perfectly. The quality of the material is equally important, and if you don’t think so, hold a Savile Row suit next to something from Men’s Wearhouse sometime and you’ll see it immediately. Last is durability. With proper care, a good suit, and a good pair of shoes, can last for years, if not generations, making it the more cost-effective buy over time.
There is also more variation to men’s shoes than many people might think. Sure, there are the basic black Oxfords and penny loafers, but there is also a wide range of other styles, colors and hides that can suit any professional or social situation. Image consultant Solomon, for instance, recommends a lace-up cap toe with a few embellishments for the office; a “fabulous” slip-on with a clean front for the same; a monk-strap that’s slightly more casual for Fridays or at the yacht club on the weekend; and another equally casual cap toe for the same.
Remeber women ALWAYS look at what you’re wearing, so make a statement of class not crass.
By the way the saying “If the shoe fits, wear it ” first came into the American dialogue in 1773: Why should Mr. Vanderbeek apply a general comparison to himself? Let those whom the shoe fits wear it.
[1773 New-York Gazette & Weekly Mercury 17 May]
(parts reprinted Forbes Magazine)


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