Best Foot Forward

Best Foot Forward

Tailoring and Footwear

Congratulations, you’ve stepped outside Kipper & Chalk with the crème de la crème of suits in hand and you’re ready to assume the role of ‘best dressed’ at the office / the wedding / the club / the senate hearing / the Mad Men costume party. But wait! One final, vital step is yet to be taken. 

A properly-shod foot can make or break an ensemble, and often tradition has dictated the way. Think of the old adage “No brown in town”, forbidding lawyers and bankers of yore from making a leather-based faux pas. However, as we are in the throes of late-stage capitalism and about to enter Q2 of the twenty-first century, tradition has lost its grip on us. Or at least our feet. So, from a purely subjective and opinionated perspective, this author will now rank the best pairings of tailoring and footwear. 

 10. The Croc


Actor Nicholas Braun from Succession



This author recommends: not wearing them


9. The Flip-flop


An important point here would be that this author doesn't count flip-flops as sandals; they will come up later on. But this one should be a bit of a no-brainer. The seamless blending of formality and casual dressing is one thing, but flip-flops (jandals/thongs to us Antipodeans) are a tad too rogue. A number of years ago at the piano bar of Los Angeles’ Chateau Marmont hotel, I observed a rather obnoxious screenwriter pitching his new idea on the phone wearing a sharp black two-piece and floral Havaianas. “Don’t call us, we’ll call you”. 


This author recommends: not wearing them


8. The Heel


Marvin Gaye

Heels with a suit has been a classic women’s eventwear combination for many a year. Back in the 1970s, there were some gloriously outlandish platform shoe options for men but sadly they have faded into the territory of fatally dated. In recent years however, heeled boots have begun to return in more fashiony circles, with Alessandro Michele’s Gucci and Hedi Slimane’s Saint Laurent. They’re not the safest option by any means, but pulling them off will result in a seriously glam look.

The former creative director for Gucci, Alessandro Michele

This author recommends: 


7. The Trainer


A flash of Nike at a Kipper & Chalk dinner

This is a contentious ranking. Many, many people would argue that trainers with a suit is now the norm and an accepted option for both business and leisure. Whilst I don’t personally endorse this style decision, the idea of having comfortable and supported feet all day is pretty tempting. When it comes to selecting the trainer, classics are always the safest bet. Think Adidas Stan Smiths, Converse Chuck 70s, and Puma Clydes. Anything too sporty or by New Balance tends to come off a bit Silicon Valley tech-bro. 


Puma Clydes worn with a Noah NYC SS23 look

This author recommends: 


 6. The Chelsea Boot


The Rolling Stones in the late '60s

Polished black, brown, or ox-blood Chelsea boots are an excellent option when one is after a certain raffish, man-about-town vibe. The Rolling Stones wore them with their suits in the 1960s, as did Andy Warhol, Jimi Hendrix, and Bob Dylan. The Beatles (you may have heard of them) had custom pairs made with Cuban heels, which became known as the Beatle Boot. It is worth noting that a slimmer or more tapered leg is best when opting for the Chelsea boot.  


Those chaps from Liverpool

This author recommends: 

 5. The Sandal


A very Pitti Uomo look

Imagine the evening Mediterranean sun gracing your skin as you sip your third or fourth white port and tonic in a Sicilian piazza, or maybe outside an Athenian taverna, or even with some tapas in Barcelona. This is precisely where the suit and sandals combination comes into its own. Two-strap Birkenstocks are the usual suspects, but a classic brown leather fisherman’s sandal is the classiest option. 


This author recommends: 

 4. The Cowboy Boot


Actor / model Luka Sabbat rocking some black snakeskin

Now this is likely quite a rogue option for many readers, and will only suit certain situations. But for those of you with a penchant for vintage Americana this could be the perfect option, especially if your suit has a bootcut or flared leg. Stick to dark browns, all-blacks, or black with white embellishment to maintain a sense of formality and Texan flair. However, if anyone says to you “Oh yeah, George W. Bush used to rock cowboy boots with his suits”, you know it’s time to hang up the spurs.


This author recommends: 


3. The Oxford


Clean black oxfords paired with rainy London

Arguably the most traditional of the list, oxfords are defined by their closed lacing, where the eyelets are set under the vamps. Whilst the term ‘oxfords’ in the U.S. can refer to any formal laced shoe, here in the UK it specifically refers to this formal construction. Commonly seen on the feet of lawyers, bankers, and businessmen, the oxford is a sleek and refined option that means one’s feet will always be taken seriously. 


This author recommends: 


 2. The Loafer


The Kipper herself demonstrating loafer superiority

The loafer is the classy option for those living at the intersection of comfort and elan. Italian tailoring loves the loafer, as does Parisian, and English tailoring has come around to the benefits of the laceless friend. For instance, ready-to-wear experts Drake’s have made the suede loafer an integral part of their uniform, often worn with white socks under a suit, topped off with a baseball cap. With styles varying from the more sleek Italian shapes to the classic American penny loafer by G.H. Bass, the loafer is definitely a world to explore.

Sharp loafer / sock combination outside Drake's, New York 

This author recommends: 


 1. The Derby


Simply a perfect shoe - bravo Church's

Perhaps I’m playing it safe here with this one, but to me the derby is the supreme choice. There’s just something about the town shoe’s ever so slightly less formal friend that appeals to me. As opposed to the closed lacing on the oxford, the derby has an open lacing system which makes it inherently less formal, and was often referred to historically as a country shoe. There are just so many routes to go down with the derby. Church’s do a gorgeous selection of top-tier sleek options, Italian brand Marsèll make beautifully unconventional round-toe options, Tricker’s provide classic brogues, and even Dr Martens would fall under the derby category. It’s the least intimidating formal shoe, and can be dressed up or down with almost guaranteed success. 


The Camden, by Grenson

This author recommends: 

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1 comment

No brown in Town?
In the now very distant past it used to be said that no gentleman ever wore brown shoes.


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