Buying a good pair of boots is kinda like buying a car. You want to find something that looks good, gets good mileage, and will last. You might have to spend a little money to get the most bang for your buck. It took me two seasons of buying the exact same pair of Aldo (a middle-of-the-road shoe brand) boots before I threw in the towel and actually spend a few hundred dollars on something nice. I haven’t regretted it one bit. It’s a worthy investment for the future.

The style, cut, material, and that sort of thing is up to you. They can be lace up or pull on, half boots or full. Don’t go for an overly trendy style, but something classic that you could conceivably wear until the beginning of the next election cycle. You’ll want to look for something you can wear from the fall and into spring, and something versatile enough that you can wear all the time, even when you’re dressed down. Something classic. Something tough.

There are lots of brands you can pick from, but what you go with depends on certain personal variables. Do you want your classic look to be a little edgy or trendier in cut? Do you want to stick within a certain budget? Let’s start with the low-end and go up from there. Most of what we’re looking at are shorter boots for men of a similar cut, because it’s a style that has staying power. They’ve been in for a while, and won’t go out of vogue anytime soon.

Timberland: No, they don’t just make hiking boots. They also make streetwear-style boots. You can get a nice pair for under $200, but note that many of them are leather upper. The West Haven ($180) is a nice pair that falls nicely in line for what you might be looking for. The West Haven Chukka ($121) is more trendy, but still solid.


J Shoes: This is a brand that delivers a stylish, edgier cut. You can find boots from J Shoes that are more or less in line with what’s hot each season, but will last a little longer than that period. They currently are running some sales on styles that are being discontinued (more on that in a minute). I like the Fellow lace-up boot found here ($230).

Red Wing: Not just for shit kickers! They actually make some good non-cowboy boot boots. Check it out: the Iron Ranger Boot ($320) is a classic look, and it comes from a company that’s been making work boots for pioneers and blacksmith types for decades and decades. They make more stylized chukka boots, as well as some styles with rubber soles for the cold wet climate-dwellers. Lots to work with here!


Wolverine: The Evans Boot is just about the platonic ideal of what I mean when I suggest a nice pair of boots. They’re 400 bucks, yes, but they will last you forever, and they will never go out of style. Honestly, most Wolverine boots fit the bill here.


One thing I would point out is a lot of these companies cut the same style of boots year after year. They may come in different colorways or have a slightly different lace from year to year, but essentially you have the same thing. Which means, most importantly, that it’s perfectly fine to buy last year’s style if you can find it on sale. They’re really not all that different and you’ll save yourself a chunk of money, especially if a style is being discontinued. Do a little research first too. Look around to see what you like. If weather permits, wait to make a purchase right after the holidays when stores are trying to purge their stock to make way for spring.

If you’re going to spend money on boots, which you should do, you’ve got to make sure they fit right, or this entire endeavor is pointless. Try them on at the store, put on socks and walk around a bit to make sure they’re comfortable, and ask the store if they have recommendations for how they should fit. Don’t forget the waterproofing polish, either. After that, you should be set for the next few years.

Top image via Getty