A guide to wearing dress boots for work & play

More than just for walking trails and conquering glacial mountain tops, the boot has come a long way from the isolate realms of the great outdoors. Learning the heel-to-toe benefits of wearing the designer boot is essential: its cross-purpose benefits and how it sits functionally in both your off-duty and formal wardrobe. Just a men’s dress boot, you ask? Let’s take a critical look at the humble piece of footwear and the many roles it can play.

The Classic Chelsea Boot

Victorian shoe makers invented the Chelsea boot and its elastic slip on heel in rebellion against the constraints of the laces typically found on riding boots at the time of Queen Victoria. Fast-forward some few hundred years and the Chelsea’s rebirth was really in the 50s, among East London’s artist scene. The Beatles started rocking the lean-look boots with pinstripe slim suits on Abbey Road, while The Rolling Stones pared them down with leather rocker denim on stage. And the rest is sweetly-tuned fashion history.

The Chelsea, named after the London area in the city’s south west, is iconic, stylish and here to stay. Equally as popular with bankers, as they are with indie types and tradies on the worksite (technically work boots are a chunky Chelsea), the Chelsea’s shoot (ankle part) is ultra functional with its slip-on fit and mid-round toe for movement.

Its variation on heel height makes it versatile: flat for casual comfort and walking ease or slightly chunkier for shorter guys (no Cuban heel here) and more formal occasions.

How To Wear Chelsea Boots

Of all of the boots, the Chelsea’s clean lines, smooth finish and lack of distracting detail make it the most refined for suits at the workplace. For the office, check out brands Adieu, John Lobb and Australia’s Aquila. Follow The Beatles cue and sport with Wall Street-look pin stripes or a suede leather bomber and jeans which ride just as well for the weekend. Rocker style Chelseas are currently offered from Edward Green, Givenchy and Dior.

The British Brogue Boot

Easily recognised by its patterned hole punch detailing, the brogue is a British footwear classic. It originated in Ireland and Scotland and is typically made in a double-layer luxurious leather or suede. As a boot, classic colourways are typically brown and black but dark burgundy and tan are just as stately. Getting down to the finer details, two types of lace options wrap up the brogue: Oxford style, with enclosed lacing; and Derby, with open lacing. The wet-weather practicalities of the brogue boot have never been so useful.

The hole patterns are designed to quicken dry-time after the shoes get wet. But more than this, they are a stylish way to personalise your look and add textural depth to boots. The perforations have even evolved over time, forming sub-types of their own. They include: full brogue (narrow toe with wing-like extensions that run the sides of the shoe); half brogue (straight toe with holes along the seam and in the centre of the toe); and quarter brogue (slim toe with holes along the seam avoiding the middle section).

How To Wear Brogue Boots

In 2018, the timeless brown brogue as a boot has found its place in the office – taken it’s not too chunky and tucked snug under slim wool trousers. Opt for a sharp black boot with cuffed camel chinos for a casual look and tweed blazer to gentrify the look. Some key brands include Mark McNairy, Hudson and Berwick.

The Derby Boot

The Derby boot, like most boots featured in this post, is a hybrid made up of the original shoe form; the derby and the boot. The Derby distinguishes itself by its laces: eyelets stitched on top of the shoe vamp, creating an open front. Thus, they are more casual and your average boot will more often than not, be made in this design style. More heritage brands that kill this genre of boot include Tricker’s, Grenson, John Lobb, Loake and Church. Contemporary makers of the derby include A.P.C, Kurt Geiger and Reiss.

How To Wear Derby Boots

The casual, hardware look of the derby (remember: open lace front panels when tied up) make it a more clumsy choice for suiting. So avoid it for super corporate looks (never with a tux). Derby boots work well with chunky look wool trousers or smooth khaki chinos and are in their rugged element with outdoor-look cottons and linen, rolled up at the hem. For a Nick Wooster-inspired look, pair with a patchwork blazer, plain tee and tailored shorts, for a show-them-off street vibe.