Ask Digby: Summer Shoes In Fall?

Ask Digby: Summer Shoes In Fall?
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Summer Shoes in Fall
Dear Uncle Digby, 
I'm trying to learn the preppy ropes but feel all tied up in knots when it comes to shoes. Am I supposed to follow some rule about no white (including shoes) after Labor Day, or do preps have a different set of rules?

Two Left Feet 
Shoe City, USA

Dear TLF,

You're on to something with that last part: preps definitely march to the beat of their own drummer, especially when it comes to beating their feet. We are the group that introduced America to the concept of dress shoes with no socks, after all. It's fine to throw some socks on, as you can see below. 

The short answer is that you can wear your summer shoes all through the deciduous autumn. By the way, isn't the word "deciduous" just delicious? Makes me want pumpkin pie washed down with scotch....

OK, I'm back. Hic. 'Scuse me. 

Now where was I? Ah yes, since preppy style is all about tradition (even if tradition is always evolving), here are three examples of historic precedent when it comes to footwear, from three different generations. 

1) Back in the 1930s, when elite colleges were playgrounds for rich boys (god I miss those days), it was popular to wear white bucks in the fall with flannel trousers and tweed jackets. You might consider the look a bit anachronistic today. Or you could think of it as a polite middle-finger to the small-minded provincials and their rules about white shoes after Labor Day. Yes, there's a polite way of using your middle finger, and this is one of them. 

2) In the '50s and '60s, the cool kids would wear their tattered old canvas sneakers even when they had to wear a jacket and tie. Here's a passage from Geoffrey Wolff's novel "The Final Club," which is set at Princeton back in the day:

Booth’s houndstooth, cut for his father on Savile Row by Huntsman during the Battle of Britain, was pinched at the waist; the boy rescued his presentation from foppery with a black knit tie and faded blue canvas Top-Sider sneakers, spattered by specks of bronze boat-bottom paint. 

3) As for the preppy '80s, have a look at the opening scenes of the movie "Making The Grade." Nearly all the boys have brown Top-Siders with khakis, Shetland sweaters, and even socks. 

So keep your favorite summer shoes in your fall rotation and you'll look cool and nonchalant, if you don't already. Just bear in mind that this does not include those flip-flop thingies. 

Carry on, 
Uncle Digby

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  • Author image
    Gene: October 11, 2018

    A follow up to the tassel loafer post — I wrote and produced Making the Grade and would have had a lot more tassel loafers if the wardrobe budget could cover it!

  • Author image
    Gene: October 11, 2018

    The cordovan tassel loafer from Brooks — an all time classic

  • Author image
    Mac: September 17, 2018

    Until snow flies I keep the cvo’s (navy & “white”) handy. I’m an old man; I need that cushioning. Wear them to the innumerable fall “fests;” strolls with the wife. Everything but duck hunting – though when the hunt is o’er, on they go after the nap.

  • Author image
    Carole schulman: October 13, 2015

    Uncle Digby I like your style, why infact I just purchased THE Jack Rodgers Loafers from CCPrep.
    They are perfect with no socks until we get a chill and then of course I will put my argyles on.
    Carrying on,

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