My apartment has a closet problem. Specifically, I don’t have enough closets to contain my borderline problematic shoe collection. At last count, I own 31 pairs—ranging from handmade Italian dress shoes I’ve worn exactly twice to beat-up Vans that should have been retired during the Obama administration but somehow keep surviving because they’re “perfectly broken in” (read: one step away from disintegrating).
The irony isn’t lost on me. I regularly advise readers to invest in fewer, better things, all while maintaining a footwear arsenal that could outfit a small village. When my friend Marcus visited last month, he stared at my shoe rack—which had long ago overflowed into a “temporary” line along my bedroom wall—and asked the most damning question possible: “Dude, how many of these do you actually wear?”
The answer was humbling. Of the 31 pairs, I regularly wore maybe seven. The rest sat in various states of neglect, some still pristine in their boxes, others worn a handful of times before being relegated to the land of good intentions and poor impulse control.
This realization led me to a thought experiment: If I had to start from zero, what’s the absolute minimum number of shoes a man actually needs? Not wants, not “would be nice to have for that specific situation that might come up twice a year,” but genuinely needs to cover 99% of life situations.
After considerable soul-searching (and sole-searching—sorry, couldn’t resist), I’ve arrived at the essential five. Just five pairs of shoes that can handle everything from weddings to workouts, business meetings to backyard barbecues. And no, this isn’t some arbitrary number I chose to make a catchy headline—I genuinely believe these five categories cover the full spectrum of what American men actually need on their feet.
Now, a quick disclaimer before the shoe minimalists come after me: Yes, you could technically get by with fewer. My grandfather famously owned only two pairs of shoes his entire adult life—black oxfords for church and work boots for everything else. He also walked eight miles to school uphill both ways, or so the story goes. But for modern men balancing work, social lives, and some semblance of physical activity, five pairs hits the sweet spot of versatility without excess.
So here they are—the only five shoes American men actually need:
**1. The Brown Leather Derby**
If I could only recommend one shoe to every man in America, it would be a medium-to-dark brown derby in a classic round toe shape. Not an oxford (too formal for many situations), not a brogue (too busy for some settings), and definitely not black (too severe with casual clothing). A simple, clean brown derby is the closest thing to a perfect all-purpose shoe ever created.
Why a derby specifically? The open lacing system (where the eyelet tabs are sewn on top of the vamp) creates a slightly more relaxed look than an oxford, making it appropriate for everything from business meetings to dinner dates to semi-formal events. In the right shade of brown, it works with navy suits, gray trousers, chinos, and even dark jeans.
I’ve had my Allen Edmonds Boulevards in dark chili for seven years now, resoled twice, and they still look better with each wear. They’ve handled boardroom presentations, wedding receptions (though not as a groomsman), first dates, job interviews, and even a surprisingly formal funeral where I realized en route that I’d forgotten to pack my black oxfords.
Price point here matters less than quality construction. Anything from Meermin ($195) to Grant Stone ($350) to Alden ($550) will serve you well if properly maintained. The key is Goodyear welting for resoling, quality full-grain leather that will patinate beautifully, and a timeless round toe shape that won’t look dated when styles shift.
**2. The Minimalist White Sneaker**
In our increasingly casual world, a clean white sneaker has gone from weekend option to weekday essential. The right white sneaker now works with everything from shorts to suits, making it perhaps the most versatile shoe in a contemporary man’s rotation.
The key here is simplicity. You want minimal branding, clean lines, and no unnecessary design elements. This isn’t about chasing trends or specific brands—it’s about finding a sneaker that won’t look dated in 18 months. The prototype is the Common Projects Achilles Low, which created the modern archetype of the minimalist white sneaker, but there are excellent options at every price point from Veja ($145) to Greats ($180) to Crown Northampton ($390) if you want something handmade.
My own white sneakers of choice are Gustin’s version, which I’ve had for four years and have developed a patina that somehow makes them look better with age—something I didn’t think was possible with white leather. I’ve worn them with everything from casual suits at summer weddings to jeans and a t-shirt for weekend coffee runs. They’ve even handled lightweight hiking when I misjudged a “casual nature walk” that turned into a four-mile trail.
The trick with white sneakers is accepting that they won’t stay pristine, nor should they. A little character builds over time, and there’s something deeply satisfying about sneakers that tell a story rather than looking box-fresh. That said, regular cleaning and shoe trees will extend their life significantly.
**3. The Weather Boot**
Every man needs at least one pair of boots that can handle whatever Mother Nature throws at them without looking like you’re about to summit Everest. This is where many men go wrong—either wearing delicate dress boots in inappropriate conditions or clomping around in overbuilt tactical boots that look ridiculous with normal clothes.
The sweet spot is what I call the “weather boot”—substantial enough to handle rain, light snow, and rough terrain, but sleek enough to wear with jeans or chinos without looking like you’re lost on your way to a construction site.
For most American climates, a Goodyear-welted leather boot with a rubber or Dainite sole hits this balance perfectly. Red Wing’s Iron Ranger with a Vibram mini-lug sole, Alden’s Indy boot, Grant Stone’s Diesel Boot, or Thursday’s Captain all fit the bill at various price points. The key is finding something water-resistant (through either the leather or treatment), with enough traction to handle slippery conditions, but clean enough in design to work in casual social settings.
My personal weather boots are Truman’s in waxy commander leather—essentially a waxed flesh-out construction that handles water beautifully while developing fantastic character. They’ve survived Chicago slush, Seattle downpours, and somehow still clean up well enough for casual Friday at the office.
The weather boot should be your go-to from roughly October through April in most climates, handling everything from rainy commutes to weekend hikes to bar outings when the forecast looks questionable. In truly extreme weather you might need dedicated snow boots, but for 95% of foul-weather situations, a good weather boot has you covered.
**4. The Athletic Performer**
The days of wearing one pair of cross-trainers for every athletic endeavor are, thankfully, behind us. However, the opposite problem now exists—specialized shoes for every conceivable activity, from trail running to HIIT classes to pickleball. Unless you’re a serious athlete in a specific discipline, this level of specialization is completely unnecessary.
What most men actually need is one pair of true performance athletic shoes designed for their primary form of exercise. For many, this means running shoes, but it could be training shoes for gym work, court shoes for tennis/basketball, or even approach shoes for hiking.
The key is honest assessment—what physical activity do you actually do regularly, not what you aspire to do? Then invest in one quality pair specifically designed for that purpose.
I primarily run and do HIIT workouts, so my athletic shoes are Brooks Ghosts—not the sexiest choice, but they handle both activities competently while providing the support my problematic knees require. They aren’t fashion statements, nor should they be. This is the one category where function absolutely trumps form.
One important note: your athletic shoes should be used exclusively for their intended purpose. They are tools, not fashion accessories, and using performance shoes for casual wear not only looks awkward but dramatically shortens their effective life by compressing the supportive materials when they’re not needed.
**5. The Summer-Weight Option**
The fifth essential pair addresses a specific seasonal need—something breathable for the hottest months when leather sticks to your feet and even the lightest sneakers feel oppressive. What this specific shoe looks like depends somewhat on your personal style and local climate, but the category itself is non-negotiable.
For most men, this means either a high-quality canvas sneaker (think Converse, Vans, or Sperry) or a proper loafer in suede or unlined leather. The key is lightness, breathability, and the ability to be worn sockless (or with no-show socks for the more hygienically minded among us).
My summer shoe of choice is an unlined suede loafer—specifically, Alden’s unlined leisure handsewers in snuff suede, which have molded to my feet like slippers while still looking presentable enough for all but the most formal summer occasions. In brutal New York August heat, they’re the only shoes that don’t feel like foot saunas after an hour of walking.
The summer shoe should be able to handle everything from shorts to linen trousers, beach outings to outdoor dining. It’s the footwear equivalent of your favorite summer shirt—comfortable, relaxed, but still put-together.
**What About Formal Occasions?**
The observant reader might notice I haven’t included a dedicated formal shoe like a black oxford. This is deliberate. For the vast majority of American men, formal events requiring black shoes occur so infrequently (often just weddings and funerals) that dedicating precious closet space to shoes worn perhaps twice a year makes little sense.
For most formal occasions that aren’t black tie, a well-polished dark brown derby (shoe #1 in our essential five) will handle the situation perfectly well. If you attend black tie events regularly or work in an ultra-conservative field like certain areas of law or finance, then yes, black oxfords become a sixth essential. But for the other 95% of men, they’re an unnecessary addition that will sit unworn most of the time.
**The Implementation Plan**
Now, I’m not suggesting you trash your existing collection and immediately buy these five pairs. That would be both financially irresponsible and environmentally wasteful. Instead, use this framework to guide future purchases and replacements. As your current shoes wear out, consider whether their replacements should align with one of these essential categories before adding anything new.
For those building a wardrobe from scratch (or recovering from a major closet purge), prioritize based on your lifestyle. If you work in a business casual environment, start with the derby and white sneaker. If you’re outdoors frequently, the weather boot might jump to the top of the list.
The beauty of this framework is its adaptability to your specific needs while maintaining the discipline of true essentialism. These five archetypes cover practically every situation the modern man encounters, from the boardroom to the bar to the ballgame.
As for me? I’ve begun the painful process of culling my collection, keeping only those pairs that serve a genuine purpose or have significant sentimental value (like the oxblood loafers I wore when I received my first major journalism award). The overflow shoe rack is gone, and I’ve discovered something unexpected in the process—getting dressed is actually easier with fewer options. Decision fatigue is real, even with something as seemingly trivial as footwear.
Will I ever get down to just five pairs? Probably not. The professional hazard of being a style writer means I’ll always have a few extra options for testing and research purposes. But I’ve found tremendous clarity in recognizing the difference between what I need and what I merely want. And in a consumer culture constantly telling us that more is better, sometimes the most rebellious act is deciding that enough is actually enough.
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