What Shoes with Smart Shorts?

So you have decided that your Gentleman’s Wardrobe should include some shorts. However, adding one item to your wardrobe simply creates a problem in another.  What shoes does one wear with shorts?

For those who subscribe to the view that shorts should be worn by Gentlemen only poolside or on the beach then the question of shoes is hardly relevant.  Flip-flops or barefeet would suffice.


If you count yourself in that category you may want to look away now… come back tomorrow for a more wholesome post…. Similarly, if you only wear shorts with a T shirt or a tank top, again this isn’t really a post for you either.

If however you do want to wear shorts in a smarter ensemble than in either of these scenarios, particularly if you are inclined to dress up your shorts even occasionally, on those occasions the question will arise, What shoes to go with them? Trainers are not a good look with shorts, unless you are wearing shorts whilst engaging a sport. Otherwise this practice should be avoided.


If you seriously dress up your shorts with a blazer then, actually, you can get away with pretty smart shoes with your shorts. Ditch the socks though…

Much more commonly however, you will dress up the shorts only modestly, with a button down collar shirt or classy polos.  In which case, you need something more casual than formal shoes and less casual than sandals or flip-flops.

Oliver Brown Deck Shoes
Oliver Brown Deck Shoes

The traditional go to shoe for this kind of context is the deck, or boat shoe. For those who like their casual shoes to be a bit chunky or to channel a preppy look decks are the gold standard.

Deck shoes have a long heritage and usually work as well with chinos and linen trousers as they do with shorts.  They come in wide variety of colours, material and prices.

CT Green Deck shoes
Green Deck shoes, Charles Tyrwhitt

However there is an alternative, worthy of consideration: the driving shoe, or drivers.  These are effectively a cross between house slippers and loafers.  Originally designed to be used in the car as deck shoes were designed for use on a boat they now have far wider usage.

Drivers are incredibly comfortable, a bit like being able to wear your house slippers when you go out. However, they are not especially durable and so tend to wear out more quickly than is typical for men’s shoes.

Driving shoes, Charles Tyrwhitt
Driving shoes, Charles Tyrwhitt

Drivers are very much on trend at the moment and can be found in a bewildering array of colours, styles, and price ranges.  The significant advantage of drivers over decks in my view is that the former are much more elegant than decks.

They more closely mirror the natural shape of the human foot, hence the natural elegance.  However, I recognise the appeal of chunky no nonsense deck shoes, especially in some of the more vibrant colours, now available.

Plum Driving shoes, George @ Asda
Plum Drivers, George @ Asda

Regrettably my shoe collection does not yet include any drivers, so I am very much on the lookout. I was surprised to discover that George at Asda has added drivers to its collection.

At the other end of the spectrum, expensive Italian bespoke shoemakers would be happy to make you a pair of drivers if you ask them nicely (and pay them handsomely as well).

Orange Driving Shoes, Charles Tyrwhitt
Orange Driving Shoes, Charles Tyrwhitt

I have ordered a number of pairs from different retailers for evaluation.  In a later post I hope to be bale to make some comparisons.

So, if you are considering adding some shorts to your Gentleman’s wardrobe, then spare a thought for the footwear need this will create.

Olive Driving shoes, George @ Asda
Olive Driving shoes, George @ Asda

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