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.


  1. David V said:

    Odd that you would see the penny in black most often when, from this end of “The Special Relationship,” we see burgundy as the most ubiquitous.

    April 7, 2012
  2. Lark said:

    That’s very interesting about the loafers – I seldom wear burgundy ones because they were ubiquitous when I was growing up in the eighties, usually in dismaying plastic-y leather. The burgundy beef roll loafer is one of very few shoes that I think truly ugly, although this is based more in childhood association than fact. Bass Weejuns, in fact, produce little but bad aesthetic memories.

    I do have a nice pair of burgundy tassel Aldens, but it took me a while to get there – I really only bought them because they look good with a wider range of socks.

    April 9, 2012
  3. Christopher said:

    Its always nice to see what the signature items are for other men. A lot of people I talk to have that one special thing that finds its way into a lot of the wardrobe.

    I don’t have one item. For me its color. Some kind of bright noticeable color gets added to every outfit.

    The grey blazer is a nice touch. It’s different enough thanks to the color. The traditional Navy one is just to old school for me to do every day. Not that I haven’t worn one. I own two in fact.

    The shoes are a great pair. Really outstanding and incredibly versatile too. Everyone needs that color shoe. They’re a great finish touch to an outfit.

    Thanks for sharing.


    April 9, 2012

Comments are closed.