Elegant Loafing


Laces: who needs them? When I was a young lad at school, purchasing shoes was a regular activity. My feet grew rather quickly in my early teens and I was taken to Russell & Bromley sometimes three or four times a year. From the comparatively small selection available in their woefully decorated stores (Eighties kitsch), I nearly always pointed to slip-on shoes. As a wide eyed and naive child, I had no tolerance for acknowledging timeless style or the hoarder’s instinct to collect ‘essential’ shoes. Slip-on loafers appealed to me because they were ‘cool’; they were untucked shirts and ink-stained trousers, the knowing grin of the worst behaved boy in the year and the loud, battered jalopies screeching from the school gates at a quarter to four. Buying them represented access to the world of the scruffy and popular; not buying them meant relegation to the ranks of the laced-up lab crew – the sort of people who now possess houses, careers and a Mercedes Benz. Oh, the utter stupidity of youth.

Now, loafers mean far less to me. I am certainly taken by a dashing design and interesting colours but I now prefer the structure and the drama of a lace-up. Having said that, loafers have always been important shoes when spring gives way to summer; especially my Tod’s driving shoes. Try as I might to find discomfort with my penny loafers, they have been faithful and extraordinarily practical; a duo of burgundy and black shoes from Bass Weejun they have retained their classic shape well throughout years of service. Indeed, to me it is clear that it is the loafer that is the Bordeaux of shoes. When spanking new, they look a little stiff, if a little dull. Once they get accustomed to the foot inside, they relax; they age beautifully and gracefully and even in old age, when they have ceased to be suitable for metropolitan rendezvous’, they make fabulous garden shoes.

There is still a healthy public demand for loafers. Pennys are rare, and for many less nostalgic than myself, a little dated. Longer shapes, unconventional colours and retro styling are becoming the commonalities in modern slip on shoes. Fashion houses such as Gucci have continued their love affair with laceless shoes; indeed Italian feet-chic in general is epitomised by the naked ankle and classic loafer. Shoe giants like Tod’s and Moreschi, famous for their production of casual and yet noticeably smart slip-ons are popular as ever, despite the fact that their customer base, at least on the streets, seems to be aging. A knowledgeable pal informs me it’s a peculiarity of culture. The English are not nearly so smart when it comes to dressing down – a statement pungent of paradox but vitally true. Chaps see the opportunity of discarding their office lace-ups, generally speaking, as a chance to put their feet into a pair of snug trainers whereas Italians and other continentals prefer driving shoes and supple leathered loafers. And they are remarkably comfortable, even more so than trainers.

With our less than clement summers it is perhaps understandable that we do not turn to Mediterranean chic on the change of the seasons, but when the weather does favour those in colder climes it is a great opportunity to give a pair of elegant slip-ons a runabout; a swinging slim trouser, some exposed ankle and of course, some of that schoolboy nonchalance.


Winston Chesterfield is an amateur composer, fashion blogger, trained lawyer and style aficionado. He lives in Westminster, London and blogs at www.levraiwinston.com.


  1. Another reason to look forward to spring. Thank God for the seasons.