Wearing Boots With A Suit: How To Get It Right (16 Outfit Examples)
Wearing boots with a suit isn't difficult, but you need to avoid some common pitfalls.
Offering more character and a sharper stance than your boring old dress shoes, boots add an edge to tailoring that can’t otherwise be replicated. However, there’s no getting away from the fact that this is a slightly unconventional look, so if you don’t pay attention to the details you can quickly end up the wrong side of stylish.
Luckily, we’re here to make sure you always put your best foot forward. From boot style and fabric choice to the right trouser length, this is everything you need to know about wearing boots with a suit.
Can you wear boots with a suit?
In short, yes. But you can’t always wear boots with a suit. This look works well for fall and winter in the city, but less so for summertime in the south of France. After all, boots are traditionally a cold-weather footwear option and therefore complement heavier, textured fabrics like herringbone wool, corduroy, flannel and cashmere blends.
Try combining them with lightweight linen or cotton tailoring in summer and they will jar, making them less rugged statement and more lack of common sense. Spring/summer tailoring is of course better served by low-profile shoes like loafers and minimal sneakers, so leave boots for the three months of the year when the rain, cold and dark nights are more prevalent.
Why you’d want to wear boots with a suit
When matched with tailoring, boots show you mean business and know what you’re doing. They give the wearer a boss-like appeal that other shoes can’t mimic, transforming a regular suit into a strong, statement look.
Wear the look with confidence and boots elevate a suit from business attire into something far cooler and more experimental.
Boots with suits: how to get it right
Arguably the most important thing to consider when pairing boots with a suit is the three-inch area around where your trousers end and your boots begin. Pants that are too long will swallow up the boots, falling on them awkwardly and making them look like something of an afterthought. Pants that are too short on the other hand can look equally sloppy, making the boots stand out for all the wrong reasons.
To get it right aim for your trouser hems to finish about an inch below the tops of your boots, ensuring there is no gap where socks might be visible. This should allow the trousers to hang naturally, keeping their straight, unbroken line while also allowing the boots plenty of room to shine.
As is the case with regular shoes, picking the right colour boots to match your suit is crucial to the look’s success. Go for a combination that clashes and even the most confident of dresser’s won’t be able to pull it off.
Seeing as the boots are a statement in themselves, it’s best to stick to classic colourways. Black and dark brown boots are the most versatile options, able to be worn with navy, grey, green or even burgundy suits. Anything outside of that and you’ll be entering risky territory – fine if you’re the frontman of an indie band, but not so much if you’re a manager in a recruitment office.
As previously mentioned, boots on the whole are better suited to the colder months. So, wearing them with a breezy linen suit would just look plain wrong. Instead, you want tailoring in fall/winter-friendly fabrics like wool, flannel, heavyweight cotton twill and corduroy – materials and textures that better complement the rugged appeal of boots.
Combine a grey herringbone wool tweed suit with black rubber-soled Derbies, for example, and you’ve got a killer tailored look, ready for an important business meeting, a night at a fancy restaurant or a winter wedding reception.
Chelsea boots with a suit
The Chelsea has long been the go-to boot style for pairing with a suit. With its sleek, sculpted silhouette and high, narrow ankle, it slips seamlessly under a pair of trousers without ruining their line.
While they were born into regality – Queen Victoria was said to have originally commission the style for riding on horseback – they eventually ended up as a pop culture hit. Revolutionary bands like The Beatles and The Rolling Stones famously wore Chelsea boots with their suits, while the British Mod subculture quickly adopted them alongside their skinny three-button versions, jazz music and Vespa scooters.
Types of suit to wear them with
Given that Chelsea boots tend sit on the more formal end of the spectrum, they work best with suitably smart tailoring. You could go the full Mod route and opt for a three-button mohair suit, or tone things down slightly with a two-button, single-breasted, lightly structured design.
Think roped shoulders, slanted flap pockets and flat-fronted trousers with a mid rise and you’ll be on the right track.
Desert/chukka boots with a suit
Chukka boots are arguably the ultimate in-between shoes; not too smart, not too casual. This makes them a natural pairing for jeans or chinos, but they can also work well with a suit.
A far cry from Chelsea boots, the chukka isn’t the dressiest silhouette – with their flexible crepe soles and soft yet durable suede uppers – so they instantly add a laid-back feel to tailoring. But, like Chelseas, they too were adopted by Britain’s youth subcultures in the 60s, giving them a counter-cultural edge that isn’t lost among their legions of followers to this day.
Types of suit to wear them with
Because of their inherently casual flavour, chukka boots typically work best with similarly laid-back, unstructured tailoring. Think Italian-style suits with soft shoulders, patch pockets and cut from textured cloths such as alpaca, mohair, corduroy and silk blends.
Consider chukka boots the fall/winter alternative to loafers – wear them in a similar way and ensure your trouser hems are slightly cropped to show off their simple, two-piece uppers.
Derby boots with a suit
Derby boots are the slightly longer, more aggressive cousin of Derby shoes, meaning they work in virtually every scenario the latter does. Therefore, Derby boots are arguably the most versatile and easiest to wear when it comes to combining with tailoring.
Try them with a navy two-piece in the office, or with sharp suit separates for a winter wedding.
Types of suit to wear them with
Derbies don’t work with any one suit in particular. Team them with softly constructed, mid-weight tailoring or heavier, structured business suits and they’ll adapt like a chameleon.
The only thing you need to be concerned about is the fit of the suit. You want tapered trousers that finish one inch below the top of the boots; a jacket that buttons comfortably and doesn’t pull around the shoulders or back; and sleeves that are tailored to finish just before the end of your shirt so they show a touch of cuff.
Boots and suits outfits for men
Now you know how and when you can wear boots with a suit, here are some example outfits to inspire your own looks.
70s-inspired boots with a suit
As outlined above, Chelsea boots are a no-brainer for wearing with a suit. The boot’s high ankle and slim shape naturally fits under trouser hems perfectly, extending the line of the leg and making the wearer appear taller and thinner than they actually are.
You might be tempted to play it safe by combining a brown pair with a navy two-piece, but the look above proves you can go bolder. Here, the textured tan suit gives off a real 70s vibe but doesn’t stray into cosplay thanks to the tonal dark brown leather Chelsea boots and simple striped shirt.
Business-ready suit with boots
While Chelsea boots can give off an alternative feel, they still work well with business attire.
Incredibly smart and sophisticated, sleek black leather versions are about as sharp as boots get, so don’t be afraid to wear them with equally formal tailoring – whether it’s a charcoal double-breasted suit or classic navy two piece, as above.
Rock ‘n’ roll boots and suits
A rock ’n’ roll-inspired look is where Chelsea boots really excel. Unless you’re feeling really brave, avoid the all-black approach and instead combine black Chelseas with a grey suit (whether checked, like above, or a plain textured version).
Finish with a black knitted polo underneath to pull it all together and you’ll be the most stylish guy in the room, every time.
Textured grey suit with suede chukka boots
Boots don’t have to be dark to work with a suit. In fact, set against light-coloured tailoring black boots can jar. This light grey suit and white shirt combination is finished off perfectly with pair of tan suede chukka boots, which add a dressed down, summery feel to an otherwise standard two piece.
Classic navy suit with brown suede boots
Brown boots are arguably the most versatile you can choose. They can be worn with every suit colour outside of black, looking particularly rich when set against navy tailoring, as above.
The tonal blue pocket square and turtleneck just goes to show how effortless dressing in a single colour can be.
Fall-ready boots and suits
If you’re looking to branch out from the safety of your navy and grey suits, olive green tailoring is a contemporary option that won’t push you too far out of your comfort zone. It looks particularly good matched with other earthy shades of beige, stone, brown and tan, as shown above.
The pastel green tie, white/stone striped shirt, camel overcoat and light brown suede boots all complement each other perfectly.
Minimal suit and boots
Tailoring often looks far cooler when it’s pared back and not over-accessorised. Find a good suit that fits well and you don’t really need anything else. Well, apart from a sharp pair of black Chelsea boots, which finishes everything off with a suitable minimal feel.
Corduroy suit and tonal brown boots
For a playful take on fall tailoring, try using an earth tone palette. Here, the tan suede boots take the dark brown corduroy suit firmly out of geography teacher territory, while the white Oxford shirt and ecru sweater bring further texture and warmth to the look.
Tonal boots with a suit
Black and brown leather might be the default choices for Chelsea boots, but suede is an excellent alternative, injecting a slightly more casual feel when worn with tailoring. This is emphasised above with the shunning of a shirt and tie in favour of a ribbed roll neck jumper.
We particularly like the matching of dark grey suede boots with a mid-grey flannel suit. It’s a foolproof approach that anyone can pull off.
Black suit with black boots
Black tailoring is notoriously tricky to pull off, but there will of course be times when it’s required. And those occasions are likely be quite formal affairs.
The trick is to keep everything as simple as possible, with few accessories and a clean white shirt. Finish with classic black Chelsea boots and you’ll look about as sharp as you’ll ever be.
Country suit with boots
Suits in traditional country fabrics like tweed and herringbone were made to be worn with boots. Regular shoes can quickly be overshadowed by the weight of the cloth, but a pair of chunky Derby or brogue boots stand up to this type of outdoorsy, heritage tailoring, elevating it even further.
Boots often work as an anchor point to a look, toning things down and keeping the outfit grounded. This is especially true if you introduce elements of bold colour elsewhere. Here, a bright red roll neck is brought back to earth by a pair of natural, classic suede chukka boots, which simultaneously add another point of contrast down below.
Olive green suit and brown suede boots
Is there nothing that suede desert boots can’t do? Not only will they bring some mid-century flair to your indigo denim jeans, they also work incredibly well with tailoring. However, given they’re a slightly casual-leaning boot, it’s worth reflecting that in the suit itself. Go for something unstructured and made from heavy cotton drill and the two will work harmoniously together.
Statement boots with a suit
Using your boots to pick out an element in the top half is an easy way to pull off this look. Take this outfit as an example: the moccasin-style work boots feature tan laces and a tan midsole, which perfectly complements the similar shade of the roll neck above them, tying the outfit together and making it feel deliberate.
Black boots with navy suit
Monotone dressing at its finest. People say that black and blue don’t go together, but they’re wrong. This navy suit, black crew neck and suede Chelsea boot combination proves it.
Versatile, easy to wear and just downright cool, it’s the perfect look for when you want to make an impression without feeling overdressed in a shirt and tie.
Classic brown leather boots with a blue suit
Brown and blue is a time-tested menswear combination. If you’re stuck for inspiration in the morning and don’t know which way to go with your suit, it makes a great fallback option.
A pair of brown leather chukka boots worn with a striking mid-blue suit and brown crew neck is a modern staple look, and one that will see you from the office to the pub with ease.