Why I’m Downsizing From 31 Pairs of Shoes to Just 5 (And You Should Too)

So I’ve got this embarrassing confession to make. Last weekend, I finally counted all my shoes. Not like a rough estimate or “yeah, probably around fifteen pairs” kind of count, but an actual, sitting-on-my-bedroom-floor, going-through-every-box count. The final tally? Thirty-one pairs. Thirty. One. I mean, I work in marketing, not professional basketball, yet somehow I’ve accumulated enough footwear to outfit half my office.

The worst part? Most of them barely get worn. There’s a pair of Italian dress shoes I bought two years ago for what I thought would be “special occasions” – worn exactly twice, still looking pristine in their box like some sort of leather museum exhibit. Then there are these beat-up Vans from college that should’ve been retired around 2019 but somehow keep making it through my periodic closet cleanouts because they’re “perfectly broken in” (translation: held together by nostalgia and duct tape).

My friend Sarah came over last month to help me rearrange furniture, took one look at the shoe situation overflowing from my closet onto my bedroom floor, and just started laughing. “Jacob, be honest with me – how many of these do you actually wear?” The question hit different because I knew the answer would be humbling.

Turns out, of those thirty-one pairs, I regularly wear maybe six or seven. The rest just sit there, collecting dust and making me feel guilty every time I open my closet. Some still have tags on them from impulse purchases during sales. Others represent various “style phases” I went through – there’s evidence of my brief workwear obsession, my minimalist period, even some remnants from when I thought I needed to dress like a prep school kid (spoiler alert: I didn’t).

This whole counting exercise got me thinking – what if I had to start over from scratch? Like, if I moved to a new city with just a suitcase and had to rebuild my shoe game from zero, what would I actually need? Not want, not “might be nice to have for that one specific situation,” but genuinely need to handle 99% of what life throws at me.

After way too much thinking about this (my girlfriend can confirm I’ve been weirdly obsessed with this question for weeks), I’ve landed on five pairs. Just five. And before you think I’m being clickbait-y here, I genuinely believe these five categories can handle everything from job interviews to weekend hikes to wedding receptions.

Now look, I get that you could technically survive with fewer – my dad basically lived in work boots and one pair of church shoes his whole life. But for those of us juggling office jobs, social lives, and trying to stay somewhat active, five feels like the sweet spot between practical minimalism and actually having options.

First up – and this one’s crucial – you need a brown leather derby. Not an oxford, not some fancy brogue with a million decorations, just a clean, simple brown derby. If I could only recommend one shoe to every guy I know, this would be it. The open lacing makes it way more versatile than people realize – it’s formal enough for business meetings but relaxed enough for dinner dates or even nice casual outings.

I’ve had my Allen Edmonds pair in their “dark chili” color for about three years now, and honestly, they’ve become my default choice when I can’t figure out what to wear. They work with navy suits, gray trousers, chinos, even dark jeans if you’re going for that dressed-up casual thing. I wore them to my cousin’s wedding last summer, to job interviews, even to a surprisingly formal funeral when I realized I’d forgotten to pack anything black.

The key is finding the right shade of brown – not too light (looks weird with darker clothes), not too dark (starts competing with black shoes territory). Medium to dark brown hits that perfect middle ground. And please, invest in decent construction here. You want Goodyear welting so you can resole them, good leather that’ll age well, and a timeless round toe that won’t look dated when styles shift. Doesn’t have to be crazy expensive – Meermin, Grant Stone, even some of the better Cole Haan options will serve you well.

Next – and I know some traditional menswear guys are gonna hate this – you absolutely need a pair of clean white sneakers. I’m not talking about chunky dad sneakers or those over-designed athletic shoes with neon accents. I mean minimal, clean, probably-leather white sneakers that look like they belong in an art gallery.

This shift toward sneakers being acceptable in more formal settings isn’t just some trend – it’s genuinely changed how we dress. I’ve worn mine with suits to casual outdoor weddings, with chinos to client meetings, even with jeans for weekend coffee dates. The trick is keeping them simple. No crazy logos, no unnecessary design elements, just clean lines and quality materials.

Common Projects basically created the template everyone follows now, but you don’t need to drop $400 to get the look. I actually wear a pair from Gustin that cost about half that and have held up incredibly well over two years of regular wear. They’ve developed this subtle patina that somehow makes them look better, not worse – something I didn’t think was possible with white shoes.

Pro tip: don’t stress about keeping them pristine. A little character actually makes them better, more authentic. Just clean them occasionally and use shoe trees when you’re not wearing them. They’ll last way longer than you’d expect.

Third essential – some kind of weather boot that can handle whatever nature throws at you without looking like you’re about to deploy to Afghanistan. This is where a lot of guys mess up, either wearing delicate dress boots in rain and snow, or stomping around in military surplus that looks ridiculous with normal clothes.

Living in Chicago has taught me the importance of having boots that actually work. Not just look tough, but handle slush, rain, ice, and still clean up well enough for casual Friday at the office. The sweet spot is something like Red Wing’s Iron Ranger with a Vibram sole, or if you want something a bit dressier, Alden’s Indy boot.

I went with Truman boots in this waxy leather that basically repels water while looking better with each wear. They’ve survived Chicago winters, Seattle business trips during their rainy season, even some light hiking when friends convinced me to go on “easy nature walks” that turned into four-mile adventures. From October through April, these are basically my default shoes unless the weather’s perfect or I’m dressing up.

The key is finding something substantial enough for actual weather but clean enough in design that you don’t look like you got lost on your way to a construction site. Leather or treated leather uppers, rubber or Dainite soles for traction, and styling that works with both jeans and chinos.

Fourth – you need one pair of actual athletic shoes designed for whatever physical activity you actually do. Not what you think you should do or plan to start doing next month, but what you currently do regularly. For most guys, this means running shoes, but it could be cross-trainers for gym work, court shoes for basketball, whatever matches your reality.

I mainly run and do HIIT workouts, so I wear Brooks Ghost running shoes – not the sexiest choice, but they handle both activities well and my knees don’t hate me afterward. These aren’t fashion statements, they’re tools. Function trumps form completely here. And please, use them only for their intended purpose. Wearing performance athletic shoes casually not only looks awkward but destroys the supportive materials that make them actually work for exercise.

The athletic shoe market has gotten insane with specialization – shoes for trail running, CrossFit, HIIT, yoga, pickleball, you name it. Unless you’re seriously competitive in a specific sport, you don’t need this level of specialization. One quality pair designed for your primary activity will handle 95% of what you throw at it.

Finally, you need something light and breathable for summer. When it’s 90 degrees and humid, leather sticks to your feet and even lightweight sneakers feel oppressive. This is where personal style and climate come into play, but the category itself is non-negotiable if you live anywhere with actual seasons.

For me, this means unlined suede loafers – specifically Alden’s leisure handsewers in snuff suede. They’ve molded to my feet like slippers but still look presentable for everything except truly formal occasions. During brutal summer heat, they’re the only shoes that don’t turn my feet into sweat factories after walking around the city.

Your summer option could be canvas sneakers, unlined leather loafers, even quality boat shoes if that fits your lifestyle. The key is breathability, the ability to wear them sockless (or with no-show socks), and styling that works with everything from shorts to linen pants.

Now, I know what some of you are thinking – what about formal black shoes for weddings and funerals? Here’s the thing: for most American men, occasions requiring true black tie or black shoes happen maybe twice a year. Dedicating closet space to shoes you’ll barely wear doesn’t make sense when a well-polished brown derby handles 90% of formal situations perfectly well.

If you regularly attend black tie events or work in ultra-conservative finance or law, then yeah, add black oxfords as a sixth pair. But for everyone else, they’ll just sit in your closet collecting dust while you reach for more versatile options.

I’m not suggesting everyone immediately trash their collections and buy these five pairs tomorrow. That would be wasteful and expensive. Instead, use this as a framework for future purchases. When your current shoes wear out, consider whether replacements should align with one of these categories before adding anything new to the mix.

If you’re building from scratch, prioritize based on your actual lifestyle. Office job in business casual? Start with the brown derby and white sneakers. Spend a lot of time outdoors? Maybe prioritize the weather boots. The beauty of this system is that it adapts to your specific needs while maintaining discipline about what you actually require versus what marketing tells you to want.

As for my own collection, I’ve started the difficult process of downsizing. The overflow shoe situation is mostly resolved, and I’m keeping only pieces that serve genuine purposes or have real sentimental value (like the burgundy loafers I wore when I got promoted to senior coordinator).

Here’s what surprised me about having fewer options: getting dressed is actually easier. Decision fatigue is real, even with something as seemingly simple as choosing shoes. When you have thirty-one pairs, you spend mental energy every morning deciding what to wear. With a curated selection that all work well together, the choice becomes obvious.