Contrast sole
A contrast sole on a traditional shape is a look that suggests confidence and personality. This guy likes to have fun with his footwear and stay on trend, while still looking office appropriate. “The flash of yellow on a subtle gray upper tells me this is a guy who might surprise me," says Men's Health Fashion and Grooming Director Sandra Nygaard.
Tassel loafer
The tassel loafer definitely errs on the traditional side of the shoe spectrum. While they may not be the first choice for the 20-something ad exec, they might be a fit for his boss. Image consultant Lauren Solomon feels they answer the question, "What does a traditional man wear for casual?”Boat shoe
Nothing says “a summer in Nantucket” like these classic shoes. “They’re very New England prep,” Nygaard says, and they conjure up thoughts of salmon colored chinos. "This guy’s “classic boater represents his lifestyle—and that of his father and grandfather," Solomon adds.
Chukka
The chukka boot is for the laid-back guy with a slight hipster edge. “This is a guy who might be aware of the trends and is thrilled the suede chukka boot is back,” says Macy's Vice President and Men's Fashion Director Durand Guion.
Although the style is simple, it still manages to feel modern enough for an urban environment.Work boot
Hello, Mr. Practical. These work boots are tough enough to handle all of the challenges you might face over the course of a work day or trekking up your favorite trail."It indicates a guy who is working out in the field—or on his collection of classic cars,” Solomon says. Maybe he’s shoveling snow for a neighbor. Either way, he’s a true all-American.
Running shoe
These running shoes might not help you run faster or jump higher, but they will score you style points on your way to the gym. Bonus: You might even be able to get away with wearing them for a night out.“This is very sleek and modern. It belongs to a guy with contemporary tastes who also likes to stay light on his feet," Nygaard says.
Oxford
A classic brogue is the go-to choice for a guy who appreciates tradition and tailoring—the sartorial guy. “He loves the cut of a good suit and depends on the right shoe to complete the look,” Guion says.His attention to detail, however, isn’t limited to his office attire. Solomon points out that this is the guy who goes from suit-by-day to a rolled up jean at night.
Loafer
While a loafer might seem like an infallible choice, it’s important to keep an eye out for the shape of the toe. A squared version gives off the vibe that you bought these when your boat was docking at Plymouth Rock.“All it’s missing is a square buckle, a Pilgrim stove top hat, and maybe some knickers,” Nygaard says. Translation: Say no to square toes. Always choose a rounded option like this.
Double monk
Although an intimidating style to some, the double monk strap is a great look for a guy with confidence. "It's great for the new generation of corporate young gun,” Solomon says. He will turn his sleek foot out with pinstripes by day and a slim-fit pants by night. Tip: "The key to looking extra cool is leaving the top buckle undone,” Nygaard suggests.
Slip-on sneaker
The slip-on sneaker is a style from yesteryear that never quite seems to lose its devout following. The comfort level can’t be beat. This guy is a bit of a wild card, and he likes to pay homage to the '80s (even if he was born years after it was originally released), Nygaard says.
Clog
The style is becoming mainstream again and can work for a low-key weekend. (It no longer only reminds you of the granola dude who lived down the hall in college.) But it should be worn with caution—and never to a restaurant.
Chelsea boot
This guy has a sleek aesthetic and knows how to style himself. "He prefers slim fitting everything and understands there are limited shoe choices to pull off the right look," Guion says.There’s only one caveat: “Make sure the shape of the shoe isn’t too skinny, or he’ll end up looking like the 5th Beatle," Nygaard says.
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