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The Modern Man’s Guide to Dress Shoes

Most guys have that single pair of black dress shoes they never think twice about until the sole starts to separate from the “body.” This article is a practical look at the shoes every man needs for a strong wardrobe foundation.

From dress boots to oxfords, derbies, and loafers—here’s a look at the staples of the men’s shoe game, as well as some of our picks perfect for any guy’s wardrobe.

The Basic Lace-Up

The basic lace-up shoe diverges into two distinct categories—the oxfords and derbies. While many people get the two confused, there are a few marked differences between the two.

The easiest way to tell them apart is the laces. Derbies have open laces, while Oxfords have closed ones. Oxfords have a line of stitching beneath the vamp--which gives the shoe a sense of formality.

Oxfords are the formal shoes that will see you through many a special occasion--from weddings to funerals, galas, and date nights. While many men feel they might not need a pair of formal dress shoes--investing in a pair might be a good idea if your budget allows. There's nothing worse than feeling underdressed at an unexpected formal event.

  • Jack Erwin, $195: A dignified shoe with a full grain construction, Jack Erwin brings a hint of broguing to the table—see the perforations along the cap toe and laces. The perfect “basic” work shoe, with a little flair—this solution goes with just about any outfit you can dream up.

  • Kenneth Cole, $148: In black or cognac, Kenneth Cole’s leather cap toe is a good shoe for the man on a budget. A barebones—but in a good way—workhorse, the Chief Counsel oxford is just as much at home in the office as it is getting drinks after work.

Derbies

The derby shoe is best described as the first shoe you bought out of necessity--they've accompanied you to your first school dance, job interviews, and a whole host of events ranging from semi-formal to business casual.

The open space on the vamp lends derbies to more flexibility. They're not as formal as an Oxford, but you can wear these with blue jeans or dress pants alike.

  • AMI Polished Leather Derbies, $485: A casual take on a classic shoe, these derbies are perfect for the informal office and will take your basic jeans and a sweater look to the next level.

  • To Boot, $350: The ultimate clean work shoe—To Boot’s Buchanan can be worn everywhere from weddings and funerals to the boardroom. Super soft calf leather and rubber soles make this choice a no-brainer no matter what your style.

Brogues

Brogues—a type of oxford shoe—are known for their perforated detailing. While something of a statement shoe, they tend to go with just about anything. Working well with sports coats and button-downs, as well as your more casual wardrobe staples, these are a part of your shoe wardrobe that can stand to break with tradition a little.

That said, these are a pretty specific type of shoe—and we’d advise in investing in a pair of wingtips only after you’ve got your plainer derbies or oxfords on lock.

  • Florsheim, $125: The Castellano wingtip is a more subdued take on the brogue. Available in a range of neutrals, this shoe features a leather upper and a cool, wood-look sole.

  • Russell & Bromley, $263: Russell & Bromley’s handsome Southport is a vision in tan calf leather. With its rubber sole and heritage, wing-tip broguing—this style looks awesome with jeans and chinos alike.

Boots

Seemingly hard to pull off, leather boots are really versatile. Rugged meets polished; few shoes do so much for a man’s outfit. First of all, they bolster the ankles from any incoming chills—something your flashy, low-heeled brogues just can't do.

Leather Brogue Boots: These guys are a brogue-boot hybrid. They're dressy, but masculine and work well for an updated take on business casual, as well as just a basic weekend outfit.

  • Allen Edmonds, $445: While these boots may seem like an investment, the gorgeous burnished walnut color goes with all your favorite outfits, and keep bad weather from soggy-ing your socks.

  • Grenson, $295: Hiking boot meets brogue, Grenson’s take on the wet weather classic features Goodyear welting and a rubber outsole.

Chelsea Boots: Chelsea Boots are a slip-on style, with elastic at the ankle that makes them comfortable and easy to slip into. These are the perfect boots to wear to work during the winter and can go easily from day to night--due to their inherent versatility.

  • Aldo, $150: Versatile, affordable, comes in a few different colors. Works best with slimmer pants across the board—chinos, jeans, trousers.

  • Frye, $328: These cowhide Chelsea boots slip on with ease and go with just about any outfit. With Goodyear welting and a leather outsole, it’s clear Frye hasn’t skimped on quality.

Loafers

Tassled, penny, or unadorned, the loafer is something of a divisive shoe—but a versatile one nonetheless. It can be dressed up or down, worn with slim-fit chinos, denim, or pattern shorts. The tasseled loafer is a slightly "cooler" version of the penny loafer--a laceless, low cut shoe with some flair.

Lean into some color experimentation--blues, greens, oxblood--but know that this style tends to go best with fitted pants or shorts and either a slim trouser sock or no socks at all.

  • GH Bass, $110: The “Weejun” loafer is part of an 80+ year tradition, and you can’t go wrong with this versatile—and relatively affordable—addition to your wardrobe. Additionally, the brand offers the shoe in everything from two-tone tartan to tasseled blue leather.

  • Ted Baker, $220: Ted Baker’s tasseled Grafit loafer is another relatively affordable loafer—with its almond toe and contrasting textures—we like the navy best. A departure from black, yet still super versatile, this is the perfect jolt of energy your workplace basics need.

Some Parting Thoughts on Color and Style

If you're on a tight budget, you don't need to buy the full spectrum of men's shoe options to make an impact. Keep it simple with a couple of pairs of the essentials.

We’re thinking a black pair of derbies, plus oxfords or a badass pair of boots. If you’re good in the black shoe department, you’ll get more mileage out of limited options if your second pair is a color like a cognac, oxblood, or even navy. Variety is the spice of life, man.

If you're all set on the standard fare, branch out a little--think suede brogues and driving moccasins in more exciting colors--teals, reds, browns, white, whatever strikes your fancy. Look at tassel loafers that add more interest to a pair of trousers and a button-up—a real game changer especially if you’re the type of dude that lives in neutrals 24/7.

Finally, it’s worth stating the obvious. Good shoes are always worth the investment. You don't want good tailoring to go to waste because you cheaped out on some pleather-y abomination.

Images courtesy of Mr Porter.

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