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The Three Boot Collection: Getting the Basics Down

Three types of boots to rule them all.
William Barton

Boots, Leather, Heritage Fashion, Denim, Workwear

William founded BootSpy in 2020 with a simple mission: test and review popular men’s boots and give a real, honest opinion. Since then, we've welcomed over 5 million readers on our boot reviews and boot care guides. Reach out to him for your own personalized boot recommendation at william@bootspy.com. Or join 50,000+ subscribers on the BootSpy YouTube channel, or send him a message on the BootSpy Instagram. Read full bio.

Last Updated: Mar 15, 2024
4 min read

Usually the first boot choice is easy.

One day, you’re browsing the web or you’re walking down the street, and you see someone wearing a pair of boots that immediately look above the pack.

For me, that first one was the Thursday Captain.

But I get asked a lot: what should my second pair of boots be?

I have something like 60+ pairs of boots (it’s an occupational hazard, you could say). But you’d be surprised at how few boots I actually wear on a regular basis. And that got me thinking: what’s the ideal three boot collection?

I’m going to break this down into the types of boots I’d look for if building a three boot collection, plus give some specific recommendations based on budget.

Boot #1: A Simple Brown Service Boot

Versatility is key. For your first boot, I recommend a simple brown service boot. You can opt for a cap-toe or go with a classic plain toe. But in my opinion, the more simple, the better.

Here was my first high quality boot:

Thursday captain boots on wet ground
Wearing my Thursday Captains (which I wore for over 5 years).

What I like about the Captain specifically is that the leather matched well with both blue and black jeans, and the silhouette of the boot was slim and modern.

When you’re picking out your first boot, I recommend the most middle-of-the-road brown you can get:

Best Color Brown for your First Pair of Boots
On the bottom right is the Grant Stone Diesel—the best “bang for your buck” service boot in my opinion.

The closer you get to “milk-chocolate” brown, the better.

If your budget is $200, then the Thursday Captain is my recommendation. If you have some more room in your budget, then I recommend upgrading to the Grant Stone Diesel.

Boot #2: A Dress Boot

Beckett Simonon Elliot close up bordeaux leather
I really like my Beckett Simonon Elliot boots for dressy situations

If you work in an office with a dress code, then a dress boot might even be your first pick. But in any case, I think having a dress boot on hand is a must.

There are some fantastic dressy options out there for relatively inexpensive. For me, I only really wear my dress boots to weddings, church, and the infrequent date night with my wife.

So I also spend the least amount here.

That said, dress boots are really all about the leather, and that’s where things can get really expensive if you want to ball out.

I like a slimmed down style with a bit of brogue detail. As long as the leather looks rich, you’re good to go.

model wearing meermin chelsea boots at table
If you don’t need a dress boot, consider a Chelsea boot. You can style them rugged or dressy depending on the day.

If you don’t think you have enough use-cases for a dress boot, try something like a Chelsea boot. While it’s not technically a dress boot, it can work as one in a pinch.

My personal go-to dress boot is the Beckett Simonon Elliot.

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Beckett Simonon Elliot Balmoral Boot
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Made with buttery smooth full grain Italian leather, the Elliot Balmoral boot offers a restrained brogue pattern and a formal closed lace construction.

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You wanna see what kind of damage this boot can do? Here’s me tearing up the dance floor in these boots at the last wedding I went to:

How to Dance at a Wedding
Absolutely shredding the dance floor.

Boot #3: A Work Boot

For a lot of guys, boots are only for work. At BootSpy, my first consideration for boots is usually style.

But that doesn’t mean you don’t need a good pair of work boots.

If you’re only interested in heritage style, then something like the Red Wing Classic Moc might be the way to go.

Red Wing Moc Toe boots
These are my Red Wing’s in Slate Muleskinner leather.

With a heritage work boot like Red Wing, when you wear it for actually working, then your boot just gets more beat up and looks better and better.

I also really like the Thorogood Moc Toe as a work boot. I don’t think it’s nearly as good looking as the Red Wing, though.

But assuming you’re here for the style, my top recommendation for a work boot that can do double duty on the style front is the Red Wing Classic Moc.

Red Wing Classic Moc

The Red Wing Classic Moc Toe boot has quite a large toe box, which can be off-putting for some, though it’s an ideal match for American Heritage workwear aesthetic. The Puritan Triple stitching, 360-degree Goodyear welt, and thick full grain leather footbed all make for a beast of a boot that will easily last years.

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That said, if you have cash to burn and time to wait and you want the beefiest work boots on the planet Earth, check out Nicks Handmade Boots.

Nicks Moc Toe profile view
Nicks overbuilds their boots. It’s awesome.

These things are nuts.

Nicks Boots Moc Toe Wedge

Nicks Moc Toe Wedge boots are an investment, for sure, but they’re the smart one every time. Not only are they incredibly durable and versatile, but the spacious construction, excellent support, ample padding, and handsome good looks make them a pair of boots you’ll be glad to wear both at work and around town.

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Got a Perfect 3 Boot Collection?

Let me know what your perfect collection is in the comments below. Whether it’s styles of boots, or what the brands are specifically.

I made a video last year where I tried to narrow down to three boots. I got to five, which is still pretty good for a boot nerd like myself:


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  1. My Dress boot is a Rancourt Danforth, which looks very similar to an AE Dalton and I got mine in a rich chocolate brown. Then, I have a pair of Red Wing goretex moc toes for those wetter days. Additionally, to add some flare, a pair of caramel comfort craftsman chelsea boots from RM Williams. Finally, and I know its beyond 5, I have 3 different pairs of Iron Rangers (Ebony Harness, Indigo Roughout, and Oxblood Mesa), to round it out. Besides my chelsea boots, as it starts to warm up, what might you recommend to help roundout my footwear for the saddle seasons and warmer months ahead?

  2. 3 boot collection ( no price limit )
    Viberg service boot 2030 last.
    RM Williams Craftsman Chelsea.
    JK work boot ( any model ).

  3. David S JONES

    Hmmm only 3?! I’m up to 11 pairs now, so let me think:
    BROWN SERVICE BOOT: Warfield & Grand Heist (or Trench because the Heist is on clearance and may be discontinued). I do have Thursday Captains (in Horween), but I really like my Heist (and they are darker)!
    DRESS: Warfield & Grand Porter (Brown – discontinued) or Warfield & Grand Trench (Black – or Apron toe – also discontinued)
    WORK: Danner Sierra or Acadia
    My collection:
    Thursday Captain
    Danner Acadia and Sierra
    Ariat and Justin cowboy boots
    Rocky Wonderboot and Side-Zipper Jump boot
    W&G Porter, Hills, Heist, Apron Toe, Battery (2-tone – also a great dress boot) Can you tell I like Warfield & Grand?!