I Can Only Fit 10 Pairs of Boots in My Apartment; Here’s How I Chose Them

Unless you are exceedingly wealthy or ridiculously lucky, a person living in Manhattan — indeed in most of New York City — must confront the reality that there is never enough space. I ran out of places to put more books sometime in the late 1990s, and ran out of space to store clothes and footwear soon after.

So for a long while now, I can only make room for a new suit, or a new pair of shoes — and the list goes on and on, including underwear and socks! — by getting rid of something first. When it comes to the boot collector, there is an added challenge: the height of most boots makes them trickier to fit into places that you might use to accommodate shoes.

Was thinking about all this when Nick asked me if I might write something for Stridewise, and it made me realize how tactical I have become in maintaining a collection that both fits the space that I have and can cover the broad range of styles that are required for work and play.

To put numbers to all this, I have room for a grand total of 20 pairs of shoes, boots and sneakers here in my Manhattan apartment, and since my other half would never let me leave footwear strewn around our place, I have slots for exactly ten pairs of boots. Those ten boots span the gamut of styles that appeal to me, from the rugged to refined, so I’d like to use all of this as a set up to review my choices, and suggest a tactical approach for planning your own collection.

[How can you afford so many boots? Check out these 11 tips to saving money on boots!]


I call the boots in this section “flexible choices” because they are great everyday boots that can be worn in a range of rugged to casual styles.

red wing 875s

1. Red Wing 875 Moc Toe (Oro Legacy)

The #875s are classics, both in style and in that gorgeous Oro Legacy color. Mention Red Wing Boots to someone who knows about them and these six-inch mocs are likely to pop into their mind. These are easy go-to boots for frequent daily wear, the color contrasting perfectly with virtually any shade of denim or khaki. I’ll wear them for a smart, casual look with sweaters and denim jackets, but I tend to avoid wearing them with dark jackets or coats. They are both timeless and retro, conjuring up the workboots my friends and I wore back in high school.

[Pick up the classic, flagship Red Wing Moc Toe in Oro Legacy here!]

red wing 9075 moc toes

2. Red Wing 9075 Classic Mocs (black harness leather)

These are the fraternal twins of my #875s, and much of what I wrote about above applies to them. Once again, these are great everyday boots, and are an especially good match when I am wearing darker pants and jackets — such as a black leather jacket, which I would never wear with my #875s.

The only reason I would not recommend these or the #875 as the choice “if you could only own one pair” — read on to find out what single boot I would recommend in that category — is that they do have a “workboot” vibe that might not cut it at the office, so depending on your job, you might not wear them as much as you’d like to. (As a music promoter, I can wear them almost any day, unless I am wearing dress pants or a suit.)

[See our full review of the Red Wing Moc Toe]

red wing huntsman

3. Red Wing 2015 Huntsman boots (black Klondike leather)

These limited edition boots were issued in 2015 to celebrate the 110th anniversary of Red Wing and they have developed a slightly cult-like following. I bought them unassumingly the year they came out, and I could not believe how frequently Red Wing enthusiasts asked me where I got them. These handsome 8-inch boots are very versatile, and can easily be dressed up or down. They almost work as a “only one pair” selection, but the soles on the original boot don’t really manage slick terrain well. With a bit of snow on the ground, I have found walking around New York City with them somewhat treacherous. But with a pair of wool slacks and a cozy sweater, you have the perfect boot for a long, well-dressed walk around the city.

alden x j crew indy boots

4. Alden X J Crew 405 Indy Boots (burnished tan)

These Indy boots, a special Alden collaboration with J. Crew, were my go-to years ago for adding some rugged texture to my casual work style. Though they look good with jeans, and with all kinds of other pant styles — even less dressy-looking suits — I find myself wearing my Red Wings much more often with the kinds of selvedge denim that have become my staples over the past couple of years. While these are very versatile boots, I would not put them on to walk around a muddy field in Central Park.

[See our review of the original Alden Indy boots!]


There are two main reasons to wear true rugged-style boots. First, they look badass. Second, in certain weather and terrain conditions, they offer some essential protections.

whites boots x bakers boots bounty hunters

5. Whites Boots x Baker’s Shoes Bounty Hunter (brown dress leather)

My number one rugged boot — perhaps my favorite boot in my collection — is a customized Whites Boots Bounty Hunter available exclusively from Baker’s Boots. With help from my buddy @Gageallenphoto, I picked all of the details for this boot. I wore these boots all winter, and because I didn’t pick a lug sole, I could wear them to the office. They kept me warm, and they stood up well to the weather. At ten-inches tall, they are not a year-round boot. But they sure make me feel badass when I wear them!

[See our review of the original White’s MP Service Boot!]

chippewa engineers

6: Chippewa Engineer Boots (black oiled leather)

Pull these boots on with a leather jacket and you feel ready to kick some serious butt. Some folks like my buddy Jake wear engineers all the time, but for me they are more of a specialty item. The other challenge is that I tend to wear slim-fit jeans these days, so engineers are often too wide to fit under them. The stylish, upstart @twothousandnever2000NVR has responded to that issue by adding a zipper to their engineers (more on those boots in a future post).

[Buy the Chippewa Engineer boot here.]


alden suede chukkas

7: Alden 1492 Unlined Chukka Boot Flex Welt (dark brown suede)

The only boot in my city collection that I would classify as “refined” is a pair of dark brown suede boots from Alden. They are as soft as butter and as light as slippers. I have worn them with jeans, and with a light-colored Italian suit, and they look great with either. But I wouldn’t want to get caught in a downpour with them, or count on them for much support if I’m gearing up for a day requiring a lot of walking around town. You definitely want to give these boots a hit of water-repellant protection at regular intervals to keep them from getting damaged or stained.

[Related: Chukkas vs Chelseas, Which Is for You?]


clarks desert boot

8: Clarks Original Desert Boot (sand suede)

My go-to casual boot in warm weather is the classic Clarks desert boot. I only wear them in the summer, and with a pair of jeans and a tee, they are about as light and chill as you can get. An easy, essential purchase.

[Get these boots for the best price on Amazon here.]


lucchese jonahs

No. 9: Lucchese Jonah Roper Boot (Espresso suede)

I call my Lucchese Jonah boots hipster boots because that’s how they make me feel when I wear them. They are the only Western-style boots in my city collection, and I’m amazed at how many people ask me about them when I wear them. The sleek styling somehow conjures up 1960s cool, but they tend to take on the character of the clothes that you wear with them. In that respect, they are extremely versatile.

I have worn them to cocktail parties and other nights out on the town, to meetings with artists I represent, and to dinner with friends. I especially like how they look with a pair of jeans and a sweater or turtleneck. I avoid wearing them in soaking-wet conditions, but I don’t try to keep them clean. I think these boots look best beaten up. These are beautiful, extremely well-made boots.


red wing klondike round toes

Number 10: Red Wing No. 9870 Round Toe (Black Klondike leather)

It’s nice to think that there is a single boot that can cover all of your needs, and lord knows some manufacturers try to market their products that way, but the truth is, very few boots will work with both a suit and a night out in a seedy dive bar, or for a meeting with a client as well as an afternoon of yard work.

But, if I could only own one pair of boots, I think my choice might be this Red Wing Klondike Roundtoe. In bad weather, when I don’t want to ruin my dress shoes, I have worn this boot with a quality suit and gotten compliments on them. I have also come home with them covered in spilled whiskey, and walked around on muddy paths with them.

Not necessarily my very favorite pair of boots, but they may just be the most versatile. And though the round-toe style comes in many colors and types of leather, something in black will go with just about anything. Some guys have told me, “I just don’t buy black boots,” to which I would offer an alternative choice: the Red Wing #2943 Harvester in Amber Harness Leather. They have a similar versatility to the roundtoes, and a rich brown color that pair well with anything from denim to khaki to wool.

Wrapping Up

I hope that by separating the boots in my collection into these categories will help you organize your thoughts about what you have and what you might think of getting next. If you have the means to own more than one pair of boots, balance out that rugged boot with something more flexible. Or if you already have a pair of mocs, step out and try a round-toe next time. Truth is, there are probably five different boots listed above that could do the trick if all I could own is one.

The main thing is: avoid buying any boot that you’re not at least 90% sure of. If you are going to spend on the average somewhere between $200 and $400 — or more — for a quality pair of boots, you should not only love the style and color, but they should also fit you well. Nothing is sadder than finally purchasing those boots you always thought you wanted and thinking, wow, I don’t think I’m actually going to wear these much. For people with tight closet space, owning anything that sits around unworn is a luxury you just can’t afford.

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Editor’s note: This article is an op-ed. The views expressed herein and in the video are the author’s and don’t necessarily reflect the views of Stridewise, LLC. Claims, assertions, opinions, and quotes have been sourced exclusively by the author.

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Albert "Upstate Guy Style"

Albert is a long-time music and performing arts promoter. Born in NYC, and a graduate of Stanford University, he splits his time between Manhattan and the Hudson Valley. He has written and lectured frequently about music, and wrote a memoir about his family that is currently in search of a publisher. Follow him on Instagram here.

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