A lot of men shudder at the thought of wearing boots with a suit. It feels like too much of a formality mismatch. The utilitarian meeting Saville Row. The everyday clashing with the elevated world of tailoring. But that’s simply not the case. Boots can be paired with a suit to great effect. Beyond this, they give your standard work day get up a point of difference from the office’s average Jo. Here, we provide instruction on how to make this subtle sartorial statement a suiting facelift. This is your ultimate guide in how to wear boots with a suit.
RM Williams Boots With A Suit
Australians love their RMs. Worn with jeans, chinos or – for the bold – shorts, these iconic boots add a touch of class to even the most quotidian of ensembles. So, adding them to a suit isn’t that much of a stretch. Look at wearing a pair of the classic Craftsman styles in either Chestnut or Black with your business suit, obviously reserving brown for navy or blue suits and black for your charcoals and greys.
Tailoring is key when it comes to wearing RMs with a suit, so focus on a shorter hem and a slim rather than skinny leg. Because boots sit higher on the foot that a standard pair of brogues or derbies, the hem also needs to sit high in order to stop multiple breaks. Leave them too long and it has the effect of looking like your pants are bunching. In a similar vein, too tight a fit in the trousers is to be avoided as it will create a break in the pleat at the top of the boots.
Chelsea Boots With A Suit
Chelsea boots come in a host of different styles and fabrics, so when wearing with a suit, it’s important to be discerning. Steer clear of pale coloured soles and instead look for a full leather construction. This looks businesslike rather than utilitarian and adds polish.
When on the hunt for a pair, look at darker shades in a high gloss rather than matte. Stockists like Paul Smith or Church’s have a great selection with interesting detailing like patterned perforations or subtly contrasting elastic gussets that can add some personality to your everyday footwear.
Wherever possible, look for a boot that has a structured silhouette – given there is usually a degree of stretch with Chelsea boots, this will ensure they remain refined and elegant over time.
Cowboy Boots With A Suit
This is a big and bold statement – particularly outside of Texas. In short, if you’re rolling with a pair of cowboy boots, you better have the attitude and swagger to match. When worn with a suit, the trousers traditionally fall over the top of cowboy boots, and they should be tailored to reflect this; slim without gripping. Don’t be tempted to tuck your pants in either – you’re a modern-day gent, not riding at the rodeo.
Because cowboy boots are a statement in their own right, they don’t need to contrast too dramatically with your suit, so look to complement the colours. Pairing caramel coloured, suede cowboy boots with a suit in sand or taupe and a plain white dress shirt or pale blue shirt makes for a surprisingly chic ensemble.
Chukka Boots With A Suit
If you’re looking for a more casual style of suiting, adding a pair of chukka boots is a perfect way to tone back a suit’s formality. These boots, often known as ‘desert boots’, traditionally come in a suede construction with either a rubber or thin leather sole.
For the purposes of pairing with a suit, look for a leather soled pair with a dark suede upper, either in black, dark brown or navy. Think about wearing with flannel trousers that are tailored with a thick cuff and, depending on the occasion, feel free to experiment with a t-shirt rather than a traditional button down. This looks casual and ensures your suit feels fresh and in line with this more laid-back footwear.
Work Boots With A Suit
Ideal for the winter months, there is a specific subset of the average work boot that defies expectation and looks sensational with either a two- or three-piece suit. However, to pull off this iteration of a suit with boots, you’ll need to look at a few very specialised State-side makers – Red Wing the most significant amongst them.
A statement in their own right, a pair of Red Wings or a similar style work boot imbues any look with rustic panache. Look to reflect this in your choice of suiting, opting for tweeds, flannels or other roughly hewn fabrics that hark back to the landed gentry and hunting tradition.
Combat Boots With A Suit
There’s something undeniably ‘punk’ about pairing combat boots with a slim suit. It represents the coming together of establishment and rebellion and, if pulled off, cuts a striking figure.
When putting together this look, seek out ultra-skinny, British-mod inspired tailoring in either bold block colours or strong geometric prints. Pair with combat boots that have a high level of polish and opt for interesting colours like Oxblood over standard black or brown. After all, this look is a nod to punk so why not play with the alternative style it embodies?
In terms of styling, tailor your trousers in an ultra high crop to show off the laces and feel free to scrunch up the sleeves or flick back the cuffs of the jacket. This ensures you have the right amount of both punk and sartorial splendour. And whatever you do, don’t stick the trousers into the tongue of your boots – you’ll look like a wannabe Indiana Jones.