Footwear Guides Perennials

Best Foot Forward: A Guide to Drake's Footwear

By Liam Jefferies

Jan 4, 2024

Best Foot Forward: A Guide to Drake's Footwear


George Glasgow Snr., master cordwainer and shoemaker to Messrs Churchill, Ferry and Lauren (née Lifshitz) once said “Invest heavily in your bed and your shoes, because if you’re not in one then you’re in the other.”

While a Drake’s Casentino mattress may be (for now) a pipe dream, the phrase rings true; more often than not, when it comes to building an outfit, shoes are the quite literal foundation, and so attention must be paid.

Many’s the great ensemble that has been foiled by inferior footwear (we’re looking at you, suit-and-running-shoes commuters) so we took it upon ourselves to develop a range of proper shoes to take you from weekday to weekend, and beyond.

Whilst we are perhaps better known for our range of shirts, ties and tailoring, for some years we have offered a selection of in-house footwear, each designed to compliment our wardrobe and ethos of relaxed elegance.

Handmade in Italy and Northampton, the twin epicentres of premium footwear, we sourced only the finest materials from the best places to find them, such as the world-renowned Horween Leather Company and Charles F Stead: Britain's master suede manufacturer.

Firmly established as part of our Perennials collection, we like to think we’ve covered every eventuality when it comes to footwear, and what follows is a guide to our family of styles.


Clifford Desert Boot

The shoe that started it all, conceived as our ‘go anywhere, do anything’ shoe, the Clifford Desert Boot was our first foray into footwear, and was borne of a need for a comprehensive, yet refined accompaniment to our soft tailoring, button-down shirts and knit ties.

Named after our former store just off Savile Row, and built using an orthopaedic last, the Clifford features an unlined suede upper, two eyelet construction and a sturdy crepe sole, making it remarkably versatile, adapting to almost any outfit or occurrence.

Our Creative Director, Michael Hill, has long been an avid champion of the humble desert boot, and notes that it was often the only footwear that would accompany his travels, rising to any occasion, so it only makes sense that we would develop our own take on the classic bit of footwear. For the Clifford we usually recommend sizing up by a half size.

As Michael says: 'A suede desert boot is a tremendously useful shoe. You can wear them to dinner, you can wear them with a casual suit, you can wear them on the weekend. If you're travelling and can only take one pair of shoes, take these.' 

Drake's Clifford Desert Boot


Crosby Chukka Boot

A sibling to the Clifford, the Crosby is a chukka boot with a three-eyelet construction and distinctive moccasin-style stitching around the toe.

The Crosby is named for the location of our first store in New York City, and has since become a bestseller and firm favourite here at Drake’s.

At once rugged and refined, rough out suede uppers and a sole in either crepe or Dainite rubber allows the Crosby to be worn as easily with denim as with tailoring, demonstrated with aplomb by Daniel Craig as James Bond.

It’s footwear that requires very little thought – just lace them up and you’re ready to go, no need to worry too much about where you’re going, or the day’s potential weather conditions. Like with all the best things they will become an effortless choice as they take you anywhere you need to go. We recommend sizing up by a half.

Drake's Crosby Boot 

Canal Loafer

Two boots down, it was time for something with a lower profile, and that came in the form of our Canal loafer.

Inspired by, and named for, the Drake's Open Studio, our shop and art space on New York’s Canal Street, the Canal loafer is a slightly beefed up, city-ready penny loafer (sans-beefroll), with moccasin-style stitching around the vamp and a hardy rubber crepe sole to keep things on the right side of casual.

Comfortable from the very first wear, the Canal is finished with a unique elliptic slot in the saddle strap, which is where you can place that eponymous penny for a sartorial nod to those in the know. 

Much in the same vein as our Games suit, it's the ideal, true to size, easy-going shoe, not just for lower Manhattan, but for anywhere and everywhere.

Drake's Canal Loafer 

Charles Loafer

While the Canal loafer takes us happily from coffee at Omotesando to nightcaps at Bar Italia, we wanted a slightly more refined model, something more in line with our made to order tailoring, and for that, only Northampton would do.

Much as Savile Row is the ancestral home of tailoring, so too is this Midlands town the nucleus of all things footwear, and so it was here that the Goodyear welted, Chromexcel leather Charles loafer was, and still is, manufactured. Only fitting, then, that we named the loafer for Charles Goodyear Jr., inventor of the vulcanisation methods used in Goodyear welting.

Taking the classic sensibilities of the original penny loafer, streamlining it and adding a distinctive saddle strap alongside a leather sole, we feel that we’ve crafted a true companion to our range of staple clothing, outside of the winter months, at least. We advise taking your true size, as like all properly constructed loafers, the Charles will widen to fit with wear.

Drake's Charles Loafer 

Murphy Chukka Boot

Which brings us to the Murphy, for the three or four months that you won’t find us in loafers, we developed the Murphy to sit handsomely alongside our range of tweeds, flannels and heavy cottons, but as our friend G. Bruce Boyer says, “the true glory of the chukka boot is that it can be worn with virtually anything, apart from swim trunks or a bathrobe that is. They look great with corduroys, khakis, or jeans, and I still think the pairing of them with a duffle coat – a post-WW II college classic look – makes for a great outfit.”

Also crafted entirely in Northampton, from the carved beechwood last to the final Goodyear welting on its open channel Dainite sole, the Murphy is to our Clifford what the Charles is to the Canal; a city-styled, elegant boot, built for longevity.

Named for Newark businessman William A. Murphy, a key figure in bringing Goodyear Welting to the fore of footwear, the Murphy features twin ringed eyelets, our signature green leather lining and waxed laces, and is constructed from a young calf skin with a luxuriously silky suede and full grain aniline reverse, soft enough for a comfortable wear, but tough enough for daily use. Fits true to size.

Drake's Murphy Chukka Boot 

August Derby

Keen-eyed observers of ours will remember the Wayford and Chard shoes, our open-laced shoes with a derby closure that served as the predecessors to what we consider is our most gracefully pragmatic shoe to date. 

Sharing a clear familial line with its kin, the August is our quintessential derby, with a sturdy, true to size, four eyelet Northampton construction, rounded plain toe, and unfussy minimalism.

Named for August Destouy, inventor of the welt-sewing machine, and matching holistically with linen and Loden alike, the Stead suede and Goodyear welted Dainite sole make the August a shoe to be worn and enjoyed for years and years… and years to come.

 Drake's August Derby




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