The Rake guide to Wearing Boots with Tailoring

When it comes to men’s footwear, boots offer up some of the most exciting style combinations. They can be smart, rugged and imposing in equal measure, and can transform an otherwise ordinary look into one with effortless style and character. Some designs have long been associated with casual clothing, with work boots and Desert boots working especially well with denim jeans, chinos and in winter, knitwear. But smarter, more formal boots can finish off tailoring like no other shoe style can. As we descend into the darker, colder months, boots make much more sense. Whereas penny loafers and moccasins complete a summer suit, a pair of well chosen Chelsea or Derby boots were practically made for heavier flannel or wool tailoring. 

Types of boot

Chelsea boots 

Of the more popular and easier styles to wear with tailoring, Chelsea boots are a great choice for those looking to invest in a higher ankle. It’s widely thought the style first cropped up in the mid 1800s, with Queen Victoria herself commissioning her bookmaker, Joseph Sparkes-Hall, to create a style that offered ankle protection while being easy to slip on and off while riding horses. This is where the definitive element of the Chelsea, its elastic side inserts, come into play. They allow the rest of the design to be form fitting and sleek, which ensures they work especially well with tailored trousers. Indeed, a pair of black leather Chelseas might be the smartest of all boot styles, combining with dark charcoal or navy tailoring perfectly. 

Balmoral boots

Rivalling the Chelsea in the formal stakes is the Balmoral. Essentially a pair of Oxford shoes with an extended ankle, they come with a ‘closed’ lace system, giving them a particularly slim, form-fitting look. Balmoral boots are also easy to spot thanks to their split design, with distinct upper and lower portions defined by a seam running along the middle of the shoe. More often than not, the upper section is crafted from suede, while the lower is leather for an interesting visual contract. First appearing in the 1800s, it is said Queen Victoria’s husband Prince Albert commissioned Sparkes-Hall to create the boots. The pair clearly had a flair for footwear design. Originally intended as a walking boot for the moors of the couple’s Balmoral Estate in Scotland, Balmoral boots are as sharp as they come. 

Derby boots 

Derby boots come in many different forms, from cap toe styles and brogues to plain leather, military-derived designs. They are a deviation of the Derby shoe, which first came to be in the late 1800s. They come with an ‘open’ lacing system, with extra panels of leather stitched on top of the vamp, rather than integrated into it. This, for many, makes them more comfortable and removes some of the formality of its Oxford brethren, ensuring greater versatility and the ability to be worn in more laid back contexts. Derby boots still work with tailoring though, although thanks to their more casual feel they work best with softer suits and separates. 

Jodhpur boots

Another riding style, designed to be worn in conjunction with jodhpur trousers, jodhpur boots are an ankle length design defined by their rounded toes and strap, which wraps around the ankle. Intended to be comfortable when riding but also smart when walking, jodhpur boots are an underrated style today. The basic silhouette is similar to Chelseas, and the elasticated comfort of the latter is often chosen in favour of the former. If you’re looking for a sharp boot that references classic country style, while still looking contemporary with single or double-breasted tailoring, this could be the style for you. 

Chukka boots 

Chukka boots are the most casual style on this list. Like the Chelsea and Jodhpur, they too have an equestrian history, specifically polo. It is thought the style originated in India during the early 20th century. Under British colonial rule at the time, they likely became popular in the west when soldiers returned home. The polo connection is somewhat contested, but given the name, which references a period of play in the sport, chukka boots are thought to be descendants of similar leather boots worn during competition. A deviation of the chukka, Desert boots came to prominence during the desert campaign of WWII, but it is the slightly more formal, slimmer lasted leather chukkas that work better with tailoring. A simple design, they come with rounded toes, two or three eyelets and a clean, minimal silhouette. 

A styling tip or two

How to wear boots with tailoring isn’t a one-rule-applies-to-all deal. The more casual chukka works best with equally more relaxed tailoring — think softer, unstructured jackets and more textured fabrics. Whereas smarter styles like the Balmoral or Jodhpur works best with smarter tailoring. Think flatter fabrics, more dramatic peak lapels and roped shoulders. But there are some rules that shouldn’t be ignored, regardless of the style you go for. 

The most important thing to consider are the trousers. Both the hem length and width should be considered. The trousers should sit around an inch below the top of the boots. There shouldn’t be any gap between the trouser hem and the top of the boots, but you also don’t want the trousers bunching up, which will ruin the unbroken line down to the shoes. Similarly, the width of the hem shouldn’t be too wide nor too narrow. The Rake would recommend nothing wider than an 8 inch hem.