Summer doesn’t exactly scream boots season, especially when there are so many great sunny-weather shoes out there. Boots are for stomping through puddles in winter, right? Well, yes and no. It’s true that heavier boot styles are going to get sweaty when the mercury tops 30 degrees, but there are plenty of lightweight, ankle-height boots that look good, and feel good, year-round. The trick is dressing with a little confidence. Summer boots are a statement. You need to feel comfortable standing out in a crowd.

This guide is for anyone who feels a bit sad retiring their Chelsea boots in November. It’s how to wear men’s boots in summer…without looking like a lumberjack.

The Dexter Chelsea Boots in Black

Summer is cocktail party season, and for the average smart-casual drinks thing, Chukka boots or military boots aren’t going to cut it. You want a sharp Chelsea boot for this one.

Chelsea boots come in high and low ankle varieties. In summer, you generally want to stick to low-ankle Chelsea boots – something like the DEXTER or LUCCA would be perfect. Because Chelseas are a little chunkier and heavier than Chukkas, you need to balance things on top. For garden parties and cocktails, we recommend a pair of dark, chisel-toed Chelsea boots (remember, the rounder the toe, the more casual the boot). Pair these with some neutral dress chinos, a pastel button-up shirt, and a light blazer or suit jacket. You can usually ditch the tie, unless the invite says ‘semi formal’, but a pocket square wouldn’t hurt.

Summer means it’s time to head back to your nearest rooftop, complete with DJ in the corner and overpriced pints. And for this occasion, desert boots are the best mens boots.

First things first, desert boots and chukkas are close cousins, but not quite the same thing. Both are a good substitute for traditional casual footwear. Even in summer. Think about it this way: would you wear high-top sneakers in December? Of course you would. Well, ankle boots are just the boot equivalent of your standard canvas high-top. When it comes to styling, just match some suede desert boots with cotton chinos and a white linen shirt. Charcoal coloured chukka boots like our BECKETT  in black will also work with cuffed jeans and a loose crew tee. If you’re unsure of the rooftop dress code, check the website or Instagram – that’ll give you an idea of the general vibe.

The Maynard Charcoal Chelsea Boots

Heading away this weekend? Of course you’ll be packing your thongs and sneakers as your go-to summer shoes, but maybe chuck a pair of military boots in the duffle bag too. Bear with us…

Military boots in summer sounds weird, but it can definitely work. If it’s a slightly cooler day, military boots and stacked slim-fit jeans is a classic and pretty uncontroversial combo, but you can also wear military boots with high-cuffed summer chinos. Pick a dark shade like navy, roll the hem a few times, and pair them with our INGRAM military boots. And when it comes to socks, don’t let your feet go commando. Military boots need mid-calf socks (preferably a light cotton blend in summer) that reach two or three inches above the shoe itself. You don’t want to show off any skin for this one.

For the summer barbecue, it needs to be something comfy and casual. You don’t want to be that guy in the knit blazer and Derby shoes, flipping patties on the grill. Enter the humble Chukka boot.

Chukka boots are a versatile summer ankle boot, and they can work with chinos, jeans, or even shorts (more on that controversial topic below…). Let’s start with some BECKETT brown Chukkas and add lightweight cotton chinos, a crew tee, and a floral short-sleeve shirt. Throw on some sunnies and you’re ready to barbecue. Alternatively, try Chukka boots with invisible ankle socks, chino shorts and a chambray denim shirt. This is a riskier play, for sure, but it can look great. The trick is confidence, and some sharp accessories: sunnies, watch and hat.

A few years ago, matching boots and shorts would have been a definite no-go. But the rules have changed recently, and boots with shorts has become a bit of an anti-fashion style statement. This doesn’t mean it’s limited to catwalks, though. Just take a pair of suede desert boots and match them with tonal cotton shorts and a crew-neck tee. You want invisible ankle socks for this look (and a healthy dose of swagger). A pair of suede Chukkas can also work with denim shorts and a long-sleeve shirt. Just roll your sleeves and throw on a cap to complete the look.

If you’re thinking of matching boots and shorts this summer, it’s best to keep in mind a few things. First, your feet will be warmer than usual. Military boots and sandals simply don’t have the same level of breathability. Second, you need to lean into the look. What does that mean? Well, in the same way that high-tops work best when they’re worn with confidence, boots and shorts require a bit of daring. Think about tonal matching, don’t be afraid of contrast socks, and balance things out with some layers on top. You’re going for an edgier, chunkier, street aesthetic, so it’s okay to feel on display. That’s kind of the whole point.

Our advice? Stick to ankle boots like Chukkas or desert boots, avoid crew socks or calf-length socks, and think in terms of tonal colours. Rocking some brown boots? Look for khakis, earth tones, and neutral shades like white and black.

The biggest mistake you can make with summer boots is actually not the boots at all: it’s the socks. If you’re wearing boots with chinos or jeans, it’s usually okay to go with standard crew socks. Just keep the colours fairly muted: navy, charcoal, earthy browns, tans and khakis. If you’re going the boots-and-shorts look, it’s generally better to go sockless, or at least wear invisible ankle socks. We generally recommend ankle socks over going sock commando: they protect your shoe, help you avoid blisters, and cut down on the odour.