Rare Moment: Preppy; Grey Blazer and Burgundy Penny Loafer

It was during a relaxed conversation with friends in a quiet and dimly lit bar that a gentleman in a blazer and striped tie interrupted us and asked us for use of a chair. My companions waved their hands silently with that careless regality of ownership, and watched as he dragged the chair over to his own table.

After a few exchanges between them, I asked what they were talking about. “No, I was just saying” said one “that he is what you would call ‘classically preppy.” Another responded saying “Yea, but I think it’s just called preppy – it doesn’t have grades of classicism.” Why not, I asked. “Because…preppy is just preppy, isn’t it? It’s a bit plain, boring. They all look the same really. It’s a uniform.” So, there’s no variety, I enquired. “Not at all. Same shirts, same blazers, same shoes…all the same.”

I could see their point, but I informed them I put this ‘sameness’ down to a lack of adventure. That there were alternatives – particularly in the colour spectrum – to the traditional.


The Grey Blazer

Of all the separate jackets in my wardrobe, there is no doubt that my navy blazer gets the most use. Every time I select a pair of odd trousers, the navy blazer is the default companion; the soda to the whisky, the tonic to the gin. It’s the wardrobe staple, and no matter how fashions come and go, the navy blazer seems to weather the change.

However, the world of blazers does not begin and end with navy. As splendid as shining brass buttons look against navy wool, there are other worthy and unusual carriers of the blazer name, most notably the grey blazer.

Whenever I have recommended odd jackets, grey suit jackets have been a good proxy for those not in possession of a dedicated separate. However, a grey blazer has a very different aesthetic to a grey suit jacket. As with the navy blazer, the buttons have the making of a proper grey blazer; dark horn is no use here.

The word ‘preppy’ is, of course, a reference to preparatory schools and there is no more identifiable fashion of ‘prep’ than a ‘school blazer.’ With some shining gilt buttons, the grey blazer is the epitome of retro uniform. Gant has a splendid example in their Rugger range.

The Burgundy Penny Loafer

Much has been written about the penny loafer. The origin of its name, its popularity at elite American educational establishments in the mid-20th century and renewed popularity in the 1980s, but few have provided a definitive recommendation of colour other than the traditional, serviceable but yawn-inducingly predictable, black.

I rarely see any other penny loafer than black. When I do, it is often tan, or sometimes chocolate suede, but the really smart alternative – the one I see the least – is the burgundy penny loafer.

My own pair of burgundy Bass Weejuns were consigned to the dustbin several years ago due to overuse. Holes had developed at the front and sides – due to my own neglect – and not a cobbler in town could rescue so sorry a shoe.

However, it was not only my sentimentality that caused me anguish, after all I had worn them virtually every day throughout my five years at university, but also my regret at losing such a convenient and attractive pair of shoes. At the end of their life, the burgundy shoes had been burnished at the extremities; rainwater, polishing and wear had aged them beautifully.

From the Archive: Style in the Movies


After doing a search for the next movie (criteria: high on style, bonus points for substance) to help me pleasantly kill hour and a half or more of my life I realized that there are many finely written suggestions to be found here in the archives of MensFlair.com. If I have managed to forget about some of these posts, I’m sure many of readers have too.

So here’s what I have dug up:

First, in the summer of 2007 Fok-Yan Leung has written about coolness factor in the movies.

Then Simon Crompton talked about his troubles in concentrating on anything but the clothes when watching a movie: The Cincinnati Kid in this particular case.

Andrew Hodges has written eloquently about few of his favorites too: To Catch A Thief, American Gigolo, Bonnie and Clyde and Diner.

Another Andrew, Watson this time, talked about how he was immensely impressed by the style in Anthony Minghella’s The Talented Mr Ripley. I personally am more a fan of the French original from 1960: Plein Soleil.

Last in the trio of Andrews, Andrew Williams, shared his thoughts on relatively newer releases: The Greatest Game Ever Played and Wall Street II.

Every list of style movies would be incomplete without mentioning James Bond. Matt Spaiser shared his expertise for an in-depth look at the five decades of James Bond’s style.

Winston Chesterfield, being a connoisseur of all things aesthetic, has unsurprisingly written the most about the subject: Easter Parade, The Great Gatsby, Brideshead Revisited, Thomas Crown, The Darjeeling Limited, Marcello Mastroianni, Unmistakable Style of Matinee Idol, Coco Avant Chanel, A Room With A View, The Brothers Bloom and The King’s Speech.

Last but certainly not least Dean Balsamo offered his inspired praise of the style in Le Cercle Rouge.

Links: Naples Shopping, Stetson Hats, A Suit Fit…


• Shopping Naples: Magnifique. (blog.styleforum.net)

• The hats of yore. (getkempt.com)

• A visual lesson in how a suit should fit a young man. (thesartorialist.com)

• Greg Chapman for Globe-Trotter.  (acontinuouslean.com)

• A very special capsule collection. (suitorial.blogspot.com)

• Shoes from around the world. (the-shoe-snob.blogspot.com)

• Spring style roundup. (ivy-style.com)

• Maus & Hoffman store visit. (thefineyounggentleman.com)

• Reservoir Dogs: gangster silhouette. (clothesonfilm.com)

• J. Gilbert’s new men’s shop. (mistercrew.com)

• Alternative style icons: John Phillip Law (asuitablewardrobe.dynend.com)

• The summer manifesto. (postmoderngentleman.com)

• Three shortfalls. (survivalofthefittist.com)

• The most imitated shirt in the world: candy stripes. (heavytweed.blogspot.com)