The Three Boot Collection: Getting the Basics Down

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:

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:

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

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.

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.

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:

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.

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.

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.

These things are nuts.

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: