Shoes: Three Style Mistakes Every Gentleman Should Avoid

How missteps in footwear can undermine even the sharpest look.

Shoes: Three Style Mistakes Every Gentleman Should Avoid

Monk Strap Shoes

"Sell in May, go away, and come back on St. Leger's Day" is a well-known financial-world adage. The Square Mile no longer has the same business and dressing cachet as it once did. However, a new generation of high-achieving investment bankers is emerging, spending their long summers prancing on the Côte d'Azur. But stepping back onto the vociferous trading floor, their moccasins and sandals will be jettisoned in favour of more formal city shoes. Gone are the days when rigid rules, such as no brown in town, dictated your city wardrobe, and a well-crafted monk strap from a renowned shoemaker, such as Edward Green, captures the semi-formal business arena. However, despite being versatile and falling between the Oxford and Derby styles in terms of formality, we often witness excessively tapered bottoms of trousers paired with the shoe. Typically, the thin, nay wafer-thin fabric of these trousers lacks the tailoring touch, leaving a gap between socks and the tongue of the shoe. It’s an unsightly appearance. Now, on the reverse, the bottom of the wide-leg or flair trouser will dramatically overrun both single- and double-strap designs, and the same if the length is kissing the sole. 
Hidden buckles deprive the outfit of the intended feeling. Robust fabrics such as flannel, moleskin cotton, covert, and even tweed, complement the shoe better, especially if they feature turn-ups. And when expertly tailored by renowned Neapolitan trouser makers like Pommella and Ambrosi, they ensure your monk strap stands out with discerning precision. Occasionally, people pair these shoes with denim pants. If the shoes are well-worn and you're wearing well-fitting pants, it might work, but the slim jeans won't do your John Lobb monk straps any justice.

Oli Lacey photographed by Kim Lang with fashion direction by Grace Gilfeather for Issue 86 of The Rake.

Loafers

This week at London Fashion Week an array of chunky platform shoes will once again spark a medley of enlightenment and criticism among the beady-eyed media gathered at 180 The Strand. This macrotrend appears to have significant longevity now. Admittedly, there are some innovative designs to marvel at. However, the attempts made on boots, sneakers and loafers were less impressive. Menswear appears to have embraced the trend, yet it remains largely unexplored in gentlemanly circles. It’s not a common phenomenon by any stretch, but there has been a surge of tassel loafers featuring chunkier soles. 
Overall, if you associate them with the shoemaking denizens of Northampton and Norwich, it isn’t really a conversation. However, in the upper-class division of shoemaking some superior tassel loafer designs, such as the Edmond model from John Lobb and the Manolo style from Barcelona-based Norman Vilalta, have made their way into black-tie soirees. The rugged Vibram commando-sole, which provides first-class grip, makes them ideal for semi-smart outdoor escapades, but the inclusion of black tie is a mistake, unlike other John Lobb shoes, which feature a single layer of leather stitched to the welt using a 'lock stitch' - these soles exude an elegant finish that is essential for black tie. Dancing the Argentine Tango with your partner in commando-sole shoes will solve any grip issues, but its romance will diminish.

O'Shea photographed by Kim Lang with fashion direction by Grace Gilfeather for Issue 93 of The Rake.

Patina

Often, it's the small details, masterfully fashioned with elite craftsmanship, that give a suit or shoe the ultimate pleasure. For most sartorial enthusiasts, the challenge is to embody the Italian concept of sprezzatura, grace without apparent effort, and gentlemen generally do not approve of attire that portrays highly flashy tendencies. Therefore, when an artisan is tasked with artistically creating a distinctive patina on a shoe, it doesn't, for the most part, admire or wash very well. It's not a classic touch and, regardless of how well-made your shoe is, it's not a wise choice if your goal is to portray self-presentation with an inescapable guise. 

Robertas photographed by Kim Lang with fashion direction by Amelia Hudson for Issue 72 of The Rake.