The first thing you need to know about men’s boots, other than which foot goes where, is that they’re not all created equal. Certain boots work better for certain occasions. Take your humble desert boot: great for the long weekend, but you’ll raise some serious eyebrows wearing it to your mate’s wedding beneath a black velvet tuxedo.
Of course, boots don’t come with helpful little labels that say things like, “Wear me to the office” or “I’m date night friendly”. That’s what this guide is for. We’ve broken down which boots you should wear for each occasion: work, weddings, dates, long weekend road trips, and everything in between.
The best way to get a feel for your office? Take a gander at what everyone else is wearing. Just remember to be subtle – staring intently at your boss’s boots is probably not a great career move. The good news is that offices, even starchy corporate offices, have become much more boot-friendly over the last few years. You can totally match your two-piece suit with a pair of boots – they just need to be the right boots.
Chelsea boots in the office
Something like the Chelsea boot is perfect for the modern office. You just need to match it to your pants. So if you’re wearing a suit, go for something a little dressier, like the Beaumont, with its long shape and chiselled toe. If you wear chinos or jeans, the Lucca is probably the better option. It’s stockier and rounder; a bit more casual-friendly. Something with a bit of character, like the Harley or the Foley, work better under suiting separates.
Chukkas and desert boots
Desert boots and suits don’t really go together, although an understated black leather Chukka, like the Adams, can potentially work. Just keep in mind: this is a much more casual look. Where Chukkas and desert boots really shine are smart casual offices and suiting separates. Try a pair of brown leather Chukkas with khaki chinos, a button-up shirt, and a knit blazer. Or maybe some suede desert boots with cuffed slim-fit jeans, a collared business shirt, and a crew knit. Something like the Brody or the Dorado is your best bet here.
Casual Friday Boots
And speaking of casual…a lot of offices like to loosen the tie on Fridays, so feel free to get creative in the boots department. It’s probably not necessary to rock up in patent leather Oxfords when everyone else is wearing jeans and sneakers. You want something comfortable, but still sharp. And boots are perfect for that.
For Casual Friday, we recommend a versatile pair of suede boots. You can wear them with slim-fit denim or chinos, and they still look vaguely professional (just keep them out of the rain, if possible). Our two most popular styles are the Eastwood, with its tall profile and Cuban heel, and the Dexter, which has a more rounded toe. The Cortes in brown can also work really well with chinos and a button-up shirt.
Date Night Boots
Dates are tricky enough, so the first rule here is wearing something that makes you feel comfortable and amazing. You don’t want to be worrying about your boots over appetisers. But for that extra special someone, we reckon you need an extra special boot. Introducing the Osbourne 2.0. This thing is like the Cadillac of Chelsea boots. It’s just about the fanciest thing we know how to make: hand-crafted in Italy, with a dip-died leather upper, so each pair is one-of-a-kind. We can’t help with the small talk stuff, but at least your ankles will look incredible.
Another great option here, especially in winter, is the military boot. These guys are heavier and chunkier than a Chelsea, but they can still look date night appropriate. The trick is to find that middle ground. Something like the Massimo or Drake is probably too heavy, too informal, but the Ingram T.D. Moro or the Sahara are just right. And remember: military boots like layers. You need to balance out the shoe with jeans, a nice shirt, a knit jumper, and maybe a woollen overcoat.
Boots at a wedding? Yep, it is possible. You just need to follow a few simple rules. First things first: check the invite. That’ll give you an idea of the dress code. And always follow your suit: there’s no point having beautiful boots if they clash with your outfit. We’ve written a handy suiting colour-match guide, to get you started.
Smart casual wedding boots
For a summer garden wedding, or anything labelled ‘smart casual’, you can get away with a sleek ankle boot, maybe under some sand chinos and a sharp, navy blazer. The Brody is a good dressy option here, with its embossed leather upper and rubber composite sole. If you want to mix things up, try something like the Keegan in grey suede: it works great underneath dress chinos and tonal suiting separates.
Formal wedding boots
If you’re going the full three-piece suit ensemble, look for something with a slim profile and chiselled toe, like the Bronson. Don't forget to match your belt, either - we've put together some helpful tips for that here. Formal wedding boots need to be dark, they need to be slimline, and they need to be understated. Because your suit pants will naturally obscure most of the boot, you’re kind of looking to copy the profile of a dress shoe. Start with the Osbourne TD Moro. You can’t go wrong.
Long Weekend Boots
Congratulations! You made it to the long weekend. Now you’re heading out of town and you need a good pair of boots to go with you. Luckily, there are plenty of great casual boots to choose from, and they make a nice change from the classic jeans-and-sneakers combo. Especially if you’re heading somewhere slightly dressy, like a winery or regional gallery.
Desert boots (AKA ‘Chukkas’) are always a solid weekend choice. With a low-to-mid cut, they straddle that line between casual and dressy. Your classic, in-between-ish sort of boot. There are plenty of colour options here, but we’re particularly partial to the Dorado Brown, with its high heel profile and soft suede upper. Just remember to think about socks. If you’re wearing these with roll-cuffed chinos, people are going to spot your ankles. We’ve assembled some handy Desert boot styling tips over here.
Military boots are one of our favourite casual shoes, especially during the colder months, when you really start to appreciate that heavy construction and high ankle profile. For the weekend roadtrip, something like the Samuel or the Massimo is the way to go: tonnes of character, a nice chunky heel, but not so fancy you’ll feel like the odd guy out. To style these, think in layers. You want slim-fit jeans (not too tight, not too baggy), some loose crew knits, scarves, beanies, and a good casual jacket. Think anoraks, trucker jackets, or heavy woollen peacoats.