I’m a boot guy. The only laced shoes I wear outside of weddings are sneakers (and even then, I wore loafers to the only two weddings I attended this summer), and if I’m not in sneakers I’m in boots. Granted, it’s less pleasant for me to stick to my guns during the Colorado summers, which regularly crest 90 degrees for months on end, and getting to slip back into my favorites is one of many reasons I love dressing in autumn and winter. These days, my tastes are running to chunkier silhouettes, and I’ve largely phased out my collection of sleek side-zip models, and with that in mind I hope here’s a selection of some of the chunky boots I’ve both enjoyed wearing and looking at online, ready for adoption into your autumn wardrobe.

Combat boots

Most combat boots that high street brands release still tend towards the dainty, and while a sleek silhouette can be nice, I think it often comes at the expense of character. I’ve been very happy with the pair of Visvim 7-Hole ’73 combat boots I bought a couple of months ago. Despite the hefty shape, they’re very lightweight, and the addition of a side-zip appeases my lazy side (it also makes them just fine to wear in an airport). Visvim has done several iterations of this boot, and past releases have sported commando soles instead. It also comes in three colors: the black, shown below, brown and khaki, and black and olive. The price of a pair of these boots is fairly high (though you can, as I did, find ways to score a deal), and in combination with the somewhat distinctive styling they’re certainly not for everyone.

To me, that’s part of the charm. It’s easy to end up with a giant shoe wardrobe with no variation in it – for example, owning 5+ pairs of near-identical side-zip boots (guilty) allows you to swap out your pairs depending on your mood, but it’s not particularly interesting. These days, I much prefer to reach into my closet for something that’s more distinctive, as it lets me change up silhouettes more than the alternative. Take, for example, these admittedly absurd Feit combat boots – they’re something of a hybrid shoe that, despite their bulk, nonetheless seems possible to work into an outfit built around a tweed or flannel trouser. Nonnative’s recurring ‘Wanderer‘ boot offers similar styling to the Visvim model, but it’s a bit too 1:1 for my tastes. Of course, if you’re after something sleek that’s a surer bet for classic and classic-casual wardrobes, I’ve always thought that Carmina’s ‘Jumper‘ boots seemed attractive.

Visvim boots shown with Monitaly x SF mountain parka and Niche patchwork jeans.

Chelsea boots

I’m not really a chelsea boot person, and that’s mostly because I’ve never loved the rocker/mod aesthetic, especially as it’s been presented in recent years. I’ve also never been certain of how I feel about an elastic gore which, despite my love of easy to put on shoes, I’ve always found a touch off-putting. Recently, this has changed somewhat, largely because I’ve taken the time to look at different silhouettes. Takes such as those offered by Common Projects and YSL have never held much appeal for me, but once again, expanding my world a bit has revealed some attractive options.

On the more affordable end of the spectrum, you’ll find boots such as the Clark’s Clarkdale Gobi. I purchased these on a whim about a month ago, and I’ve been pleasantly surprised by how much I’ve worn them. They’re a good middle-ground in terms of silhouette, and crepe soles remain comfortable. The problem, of course, is that they don’t do great when the temperature plummets, and really aren’t wearable in the snow. Even so, the lower price makes them an easy pair to test out.

Gobi boots shown with Kapital Century denim and a vintage chore jacket

If you’re looking for a longer-lasting, leather-soled model, you’ve probably already been sent in the direction of RM Williams boots. I’ve been keeping an eye on these for the better part of this last year, and there are two different models that have retained my interest: the very classic Comfort Craftsman and the Yearling, both of which are wholecuts, but which have very different silhouettes thanks in large part to the height of their respective heel. While the ‘Gardener’ model is a bit too blobby for my tastes, I appreciate the relative heftiness of the silhouettes on offer. If you, like me, are a fan of Western and Western-inspired footwear, there are a few models – such as the  – that, especially for an American, offer a wearable twist on Western wear. Sporting a pair of cowboy boots really takes some commitment (more on that later), and it’s a world I haven’t quite dived into yet, but RMW’s designs are perhaps a bit more forgiving than a full-on croc boot.

Another option that has caught my eye recently is Viberg’s chelsea boot. They’re not brand new this fall, but they offer – as does RMW – a heavier take on the chelsea. As is the case with most Viberg models, you can find it with a variety of leather and sole options, and if you want a workboot that you do’t have to lace yourself into, this is an attractive – and long-wearing – possibility.

Work Boots

By now, I’d be surprised if any forum member hasn’t heard of Viberg, and they’re still a go-to for heavy workboot styles. Every season, you can find a huge range of models at Viberg’s many retailers, but right now the makeup I have my eye on is this Scout Boot that Viberg is selling through its own webstore. Perhaps that’s because it’s fairly similar to the other boot I’ve had my eye on, which is Visvim’s now-venerable Virgil. Unfortunately, my feet don’t seem to play nicely with the Virgil’s last shape, and Viberg models lack the lightweight, sneakerboot feel of Visvim’s footwear, which is part of what makes the latter so appealing to me. New webstore Miloh Shop is also offering what I think is a pretty handsome ‘Triple Black‘ makeup that would work well with olive chinos, among other things.

If that’s not your style, you might prefer Alden’s classic moc- and plain-toe models, but I feel I hardly need to mention them here. One budget option is Timberland, a brand my cousin (a field researcher) swears by, so if you want something that might actually keep your feet dry and warm this winter they’re not a bad bet. This fall, both Nonnative and Sophnet have done a Gore-Tex and an all-black zipper-finished model, respectively, and I have to say – both look really good. Unfortunately, if you have large feet, you’re probably SOL.

Western boots

As mentioned earlier, I haven’t quite had the courage to dip my toes into a true Western (read: cowboy) boot – there’s a lot of cultural baggage for me there, and I am endlessly undecided as to whether I think I’d actually wear a pair. Even so, there are some boots out there I think are undeniably cool, and there are others that are likely a bit more accessible in terms of shape. If you’re interested in a true-blue cowboy boot, I think that Heritage Boot Co. is making some designs worth your while. They’re far more interesting than most designs you’ll find from big makers like Lucchese, and from what I’ve read they’re made to a much higher standard as well. My only experience with Lucchese resulted in two returns do to two separate QC issues, and plenty of boot people on the internet reckon that Heritage Boot is making some of the nicest boots on the market, especially considering what they’re asking for them. A few stand out to me in particular; their basic black ‘Apache,’ the French-toed ‘Ranch hand,’ and the exotic ‘Stingray.’ The first two options seem the like relatively low-risk and low-effort ways to give a boot like this a shot, while the stingray boot requires a step up in commitment. Some of the inlaid models are worth a look as well, although I imagine most people would find them a little harder to work into a regular rotation.

On the shallower end of the pool you can also find models such as the Lucchese Shane and Cannon, both of which are available via Huckberry. Both are roper-style boots with an un-embellished shaft and a rounded toe; obviously at home with denim, but potential options for textured trousers as well. At under 400$, the ‘Shane’ strikes me as a sensible entry-level attempt, especially given Huckberry’s easy return policy – I’ve seen the same model available through Amazon before as well, though you’ll have to check the shipping and return terms on your own. The Lucchese Jonah was also briefly popular on the streetwear side of the forum, and is a much, much easier boot to work into a variety of wardrobes. It’s a pricier zip roper, with a hefty sole and a slightly wider shaft that accommodates a straighter-leg jean or trouser. Unfortunately, I’m one of several people who, as mentioned, had some issues with QC, so if you’re interested in these boots make sure that you have the option to exchange or return.