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

I’ll start this article off with a confession.

Last weekend I went through every single pair of shoes I own.

And I mean, I counted every pair. I didn’t say, “Oh, about fifteen.” I didn’t give myself a wide range. I literally pulled every shoe out of my closet and threw every unorganized pair onto my bedroom floor until I knew the exact number.

You ready?

Thirty-one pairs.

Thirty. One.

That’s how many shoes I own. I’m not a professional basketball player, although somehow I’ve managed to amass enough footwear in my possession to deck out at least half my office.

Now, the sad part is that I wear about ninety-percent of them nowhere near as often as I should. I have a pair of Italian-made Arnio dress shoes that I purchased two years ago and still sit fully boxed in my closet. I wore them twice “for special occasions” and returned home from both events happy that they hadn’t scuffed or messed up the perfect shoes I somehow believed I needed. They still sit in my closet like shoes destined for a leather museum.

I have old worn-down Vans that I wore constantly in college but should’ve given up the ghost in 2019. Yet here they are squatting through my yearly closet purges because they’re “super worn in.” Translation: duct tape holding them together.

My girlfriend came over earlier last month to help me move some furniture around in my apartment, saw the obscene amount of shoes bursting out of my closet and piled high on my bedroom floor, and laughed out loud. “Jacob, honestly with me though. How many of these do you actually wear?”

Needless to say, she had me there.

Do the math. Thirty-one pairs of shoes. Maybe I wear… ten regularly? Okay, let’s be honest – it’s closer to six or seven pairs of shoes I wear on a weekly basis. The rest are dust collectors mocking me every time I open my equally overstuffed closet.

Some still have the tags on them from silly whims I had during sale seasons. Others are remnants of different “style phases” I went through trying to figure out my personal aesthetic. My shoe cupboard is littered with evidence of my workwear anxiety, dumb minimalist kicks, and even durable flannels I stupidly bought in an attempt to dress “preppier” (side note: they did nothing for me).

The crazy thing is, when I sat down and actually counted everything I owned, I started thinking about what I would need if I had to start completely over.

What if I moved to a new city and could only bring a suitcase? What if something happened to my current collection and I needed to rebuild from zero? What types of shoes would I actually NEED to own? Not want. Not “it would be nice to have for that one specific occasion,” but need in order to feel prepared for 99% of life’s occasions.

After over analyzing this for far too long (my girlfriend will tell you I’ve been weirdly obsessed with this question for the past month), I came up with five.

Five types. Once you have these five categories covered, you can build your wardrobe out from there. Don’t worry, I’ll get into what specific shoes I recommend underneath each category but first I wanted to outline why every single guy should own each type.

First, and hear me out on this because it’s important – you need a brown leather derby.

Not an Oxford. Not some brogue adorned with hundreds of little decorations and tonal markings. A plain simple brown derby. If I could only recommend one type of shoe to any guy reading this article it would be this.

Sure they’re formal, but the open lacing on a derby allows them to be so much more versatile than most people give them credit for. You can wear them to pretty much any business setting while still being able to dress them down and wear them to dinners or awesome casual outings.

I’ve had my Allen Edmonds Derby in “dark chili” for close to three years now and they’ve pretty much become my go-to shoes when I can’t decide what to wear. They pair amazingly with everything from navy & gray suits to trousers/chinos and even dark denim if you’re going for a super-dressed up casual look. Last summer I wore them to my cousin’s wedding, multiple job interviews, andahem even a funeral that I showed up under dressed for before realizing I “didn’t own anything black.”

The key is finding that perfect shade of brown. Too light and it looks weird with darker clothes. Too dark and you enter boot-cut shoe territory (which black shoes already dominate). Go with a medium to dark brown and you’ve hit that sweet right balance. And please please please spend money on a good derby. Get something with Goodyear welting so you can resole the damn things when they break down, great leather that will only get better with age, and a timeless round toe that won’t look outdated as menswear styles evolve.

You don’t need the most expensive shoe out there but investing in something from Meermin, Grant Stone, or even higher quality Cole Haan will allow these babies to last you a decade or more.

Second – and I know you’re gonna frown upon this if you’re a stickler for traditional menswear rules – but you NEED a pair of white sneakers.

Alright, not FILA Ludwins or some horrible over-produced Adidas with blinking LED lights. And please we’re not talking about bulked up dad sneakers either. I’m talking minimalist. Probably leather. Simple white sneakers that belong in an art museum.

Look, sneaker culture has ruined footwear as much as it’s evolved it. I can honestly wear my white sneakers with a suit to lazy outdoor weddings, chinos for client meetings, and yes – even jeans when I’m just running around doing weekend errands. The trick is to keep them minimal. No big logos plastered across the side. No nonsense design details. Straight up clean lines and high quality materials.

Don’t get me started on how popular Common Projects made their minimalist sneaker the “white go-to” but you literally can’t slip on a pair of white sneakers these days and not think of them. That being said, you don’t need to spend $400 on a pair to get the look. In fact, I actually wear a pair from Gustin that were half the price and have held up JUST AS WELL to two years of near daily wear.

Pro tip: don’t obsess over getting them clean or white. Let them develop some character and they’ll actually look better for it. Clean them every once in a while, stuff them with shoe trees when you’re not wearing them, and they’ll last you years.

Okay third. You need some sort of boot that can handle inclement weather.

Whether that’s snow, rain, dirt, mud, or a combination of all three you need boots that can handle mother nature without you looking like you’re gearing up for birth control missions in Afghanistan.

As a Chicagoan, I have learned the importance of finding boots that actually WORK. Sure they look tough but can they handle slush, rain, ice, and look semi-decent enough not to get laughed at when you wear them to the office on casual Fridays? That’s the goal. You want something along the lines of Red Wing’s Iron Ranger with a Vibram sole or dress them up a bit with Alden’s Indy boot.

I opted for Truman boots in this waxy leather that pretty much sheds water while breaking in and looking better with each time I wear them. They’ve handled Chicago winters, Seattle business trips in their infamous rainy season, and even some beginner hiking when my friends talked me into going on “easy nature walks” that turned into four mile adventures. From October through April these are basically my “go to” shoe unless it’s nice out or I’m dressing to impress.

Find something that can actually handle getting chewed up by mother nature but is refined enough in design that you won’t look like a construction worker who lost his way on his way to work.

Leather/treated leather uppers, rubber or Dainite bottoms for traction, and streamlined styling that can go just as easy with jeans as it can chinos.

Fourth – you need a dedicated pair of athletic shoes.

By athletic, I mean dedicated to the sport or activity you ACTUALLY DO. Not what you think you should be doing or trying to convince yourself you’ll start next month. Something to house your feet in when you do actually workout.

I both run and do high intensity interval training (HIIT) so I opted for Brooks Ghost running shoes. They’re far from the sexiest shoes but they work for both activities and my knees don’t hate me when I’m finished working out. These shoes aren’t sexy – they’re tools. Performance over fashion every time. And for the love of all things holy, only wear them for working out. Wearing bulky performance athletic shoes in everyday settings not only looks stupid but ruins the scientific support and materials that make them great for crushing your fitness goals.

The athletic shoe game has gotten absolutely crazy. There are now shoes for trail running, CrossFit, HIIT workouts, yoga, tennis, basketball, and even pickleball. Do you NEED all those shoes? Hell no. Buy one decent pair that’s designed for the activity you actually do and it’ll handle 95% of your needs.

Last but certainly not least – you need something lightweight and breathable for summer.

Don’t even get me started on how disgusting leather shoes feel when it’s 90 degrees and humid. They stick to your feet and even mesh sneakers can start feeling cumbersome when the weather turns. This is where your climate and personal style come into play but the category itself is necessary if you live anywhere that has seasons.

For me, that meant unlined suede loafers. Alden’s leisure handsewers to be exact. They’re snuff suede which has molded to my foot shape like a comfortable pair of slippers but still looks put together enough to wear with everything but the darn tuxedo. During Chicago’s brutally humid summers, these are the only shoes I wear that don’t make my feet feel like they’re sweat mining after a few blocks of walking.

Could be canvas sneakers. Could be unlined leather loafers. Could even be quality boat shoes if that’s more your style. Just make sure they’re breathable enough to wear without socks (or with no show socks) and that they styIe well with shorts and everything else you own.

“But wait Joshua!” I hear some of you protests. “What about black dress shoes? You can’t wear brown derbys to weddings and funerals.”

Sh*t sounds ridiculous, but hear me out.

If you’re an average American guy, how often do you really get invited to black tie events OR own clothing appropriate enough to wear black oxford shoes? Twice a year? Great, keep your closet space available for those other 363 days worth of shoes that YOU ACTUALLY WILL wear. Those brown derbys I mentioned above can (and have) take care of 90% of your formal occasions. Save yourself the headaches of shining black shoes and sticking to a rigid dress code.

That being said, if you’re Ephraim or regularly attend events that require black tie get wearing those motherfuckers and buy black shoes as your bonus sixth type. Just know that they’ll spend way more time drying cleaning solution than actually being worn.

Now this isn’t me telling you to go through your current shoe cupboard and chuck every pair of shoes that doesn’t fall under these categories. That’s ridiculous and would create more waste than help you build your collection.

When it comes time to replace old shoes or add to your current collection, that’s when these categories come into play. If your favorite sneakers wear out, do you REALLY need a fifth sneaker or should your budget go to replacing that category with something new?

Same rules apply if you’re actually starting from scratch. What kind of job do you currently have? If you work in an office setting with business casual attire, start with that brown derby and a pair of white sneakers. If you spend most of your free time hiking through the mountains, maybe your boots should be your number one priority. These categories are simply a guide that can be tailored to your specific needs while keeping you disciplined about ONLY buying things you actually need.

As far as trimming down my own collection goes, I’ve taken the first few steps. For me, my overflowing shoe problem has been resolved. Going forward I plan on ONLY buying shoes that fit these categories or have an actual purpose I cannot be filled by something I already own (bye bye burgundy loafers I only wore once but bought because I got promoted to “senior coordinator”).

What I’ve learned about paring down to only have footwear I wear on a weekly basis? Getting dressed actually became easier.

Sticking to this thought process of ONLY buying shoes I NEED has eliminated decision fatigue when I’m getting ready to go out. Sure I have less options, but fifty percent of my shoes I WORE WEEKLY. Every.single.day I knew what I was wearing down to my shoes. Choices became easier and my wardrobe as a whole became simpler to manage.

Brown Derby

My #1 pick for a brown derby is Allen Edmonds’. They offer some of the widest range of colors and widths, and their Derbys come in some of the best construction and materials out of any mainstream shoe brand. Think Goodyear welting, waterproof linings, and fantastic leather. My only complaint is that they’re sort of a “jack-of-all trades” and don’t offer any crazy styling details that sets them apart. I would hands down recommend their “dark chili” color. It’s a rich chocolate brown that still isn’t too dark to wear with most shades of blue pants.

My second choice is Mercer footwear. They’ve recently been on my radar and everything I’ve tried on has been great. They’re similarly priced to AE but I found the styling to be a tad more unique. Lincoln is hands down my favorite brand for slim-fitting, minimalist sneakers but their derby is pretty awesome as well. A bit more dressy than AE but still versatile enough to get away with anytime.

Lastly, I wanted to add a shoe that was nice and cheap. Shoes that won’t break the bank but can serve as that basic brown derby you can toss on with anything. McDuff’s has been making quality shoes for ages, and all of their derbys come with that signature grease saddle tan leather that ages beautifully. If you’re wanting to start low and work your way up these are the boots for you.

White Sneakers

Let’s get the obvious one out of the way first – Common Projects. Hands down the best looking minimalist white sneaker out there. Hand stitched, crazy durable, and ages beautifully. My only qualm is the price tag. At around $400 you really need to spend some time researching WHITE before spending that kind of cash.

My go-to when I want white sneakers that don’t break the bank are Gustin. I actually own a pair and they’re probably worth every penny I spent. Two years in and they look better than when I bought them thanks to a subtle patina that developed from wearing them so often. Keep them polished with some sneaker shine or toothpaste and they will honestly last you forever.

But what if white isn’t your color? No shame. Not everyone can rock off white sneakers. Check out Born’s sleek sneaker in a darker gray. The styling is identical to their white homage but allows you to ease your way into minimalistic sneakers without rocking a pair of nuclear-tipped shoes.

Boot

If you’re going to spend money on one pair of shoes, these should be the ones. Heavy duty without looking bulky. I’m a big fan of classics that will look good forever and Red Wing’s Iron Ranger is about as close to a perfect boot as you can find.

Look for something with a Vibram sole (they also make great campers) and go with a darker color. You won’t ever regret it.

Athletic Shoes

Your athletic shoes SHOULD be the absolute worst fitting shoes in your entire wardrobe. Meaning, they shouldn’t fit like any of your other shoes. Buy a shoe with crazy support, rugged traction on the sole, and fits tight. These will be the shoes you destroy so don’t be afraid to go with something boring. Again, functionality over fashion every single time.

If you run like I do, I currently have two pairs of Brooks and they are insanely comfortable. I used to swear by Sauconys but my recent trips to Brooks helped me realize that I was missing out. My girl even got me a pair for Christmas so I’m fully stocked. But if you’re looking for something less expensive, check out Hoka One One. They specialize in running shoes and have some crazy lightweight options.

Summer Shoes

Ah Summer shoes. These were BY FAR the hardest for me to pick because there’s something about slip on shoes I love. But alas, I have shoes with socks won’t breathe in July. With that being said, these Alden loafers are the bees knees. Unlined, comfy as hell, and go with literally everything.

If you’re not into loafers (boo) definitely check out Classic Charleston’s single monogram boat shoes. Made in America and completely customizable. Plus they’re only $125 which is an absolute steal.

Bonus: Black Shoes

If you decided to ignore my whole “skip the black shoes” spiel earlier and insist on having a nice pair of black oxfords in your rotation, let me help you out.

If you work in an office or dress professionally weekly, you NEED a pair of Allen EdmondsBlackstone Oxfords. They run true to size, have that beautiful Goodyear welted construction, and age amazing.

No wardrobe should be without a pair of Eastlands (seriously guys if you haven’t tried these bad boys on yet, do it). Super affordable and insanely comfortable. The stitching alone on these motherfuckers are worth the price tag.

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