Easy and Elegant Life

The Search for Everyday Elegance and the Art of Living Well.

Choose… Shoes


I know, I know. I’m one to talk. This coming from a man who once wore espadrilles to the State Department and combat boots with a blazer and flannels to school. That was then and this is now and thank goodness there is no photographic record of those days. Hindsight is 20/20 and the vision is embarrassing.

Now I’m not one to recommend that a man owns and wears one style of shoe alone. No, I wouldn’t do that to you. But I will recommend that you invest in a few that will do double duty. And by that I mean that they may be dressed down, or dressed up, to errrr… suit the occasion.

There is a constant battle over the line drawn in the shifting sands of fashion between smart casual, casual and formal. The battle is fought between those who want to be correct and those who want to be cool. Sometimes the twain do meet. Often with disastrous results. But not always.

Me? I far prefer semi-formal and formal dress. Remember those distinctions dear reader? Formal, in my day, meant dinner clothes — a tuxedo. For my grandfather it would have meant white tie and tails. Semi-formal was what we now call — erroneously if my eyes don’t deceive me — “business dress.”

So what does that have to do with shoes? It used to be said that you could tell a gentleman by his shoes. I’m not sure that’s still the case. You can probably tell and Englishman by his shoes as they will be black. An Italian will be well-shod in suede. An American? Well as our very own Mr. Porter wrote “anything goes.”

Especially in these days of business casual, smart casual, casual casual, when we are all in danger of becoming “casualties.” What to wear when you aren’t in a suit and tie? Or I should say, what do you wear with jeans, khakis and odd trousers? And can those shoes be worn when you are in the mood to step out and step up?

First the list. Then the variations on a theme.

Here is what I see as a basic shoe wardrobe.
Cap toes, 2 pairs. Black and brown. If brown, they may be suede.
(A variation here is a pair of black, plain toe oxfords or bluchers and a brown tooled captoe or full-brogue/wingtip.)

Loafers dark brown or oxblood. Penny or tassel are probably your best bets.

Monk Straps. Black or brown. I love the mahogany double monk with a floating medallion or plain toe. Captoes are always welcome. In brown, they may be suede as with the captoes above.

Boots (ankle/Beatle or lace up chukkas) for those of you feeling very rakish indeed.

Formal slippers or lace ups. You do have a tuxedo/dinner jacket don’t you?

Boat shoes, Belgian Shoes or suede driving shoes. At the beach or at a backyard bar-b-que or for grabbing a Sunday morning paper and coffee.

There, that was easy, wasn’t it?

Now then, in terms of casual wear… what goes with what? I wish I could do one of those nifty charts that lays combinations into a grid or something, but I just don’t think that way. So…. a beginner’s course.

With jeans wear: any of the above. Seriously. Just don’t wear running shoes unless you plan on running. And in jeans, running is very uncomfortable.

A case can be made for the old style Jack Purcells, Tretorns, Sperry Stripers, Adidas Sambas, Converse “Chucks” and the like, but if you’re not wearing a sweat shirt or red windbreaker, and if you are over, say… 30… I’d stay away from that look. Tinkering under the hood? Go for it. Although work boots and a vintage mechanic’s coverall in herringbone would look far better.

With khakis wear:
Driving shoes (if the khakis are very slim cut and have no break at the top of the shoe.)
Boat shoes. Especially if you’re on a boat.

With shorts:
Chukka boots (desert boots)
Driving shoes
Boat shoes
Canvas sneakers. You’re in shorts… which means you’re probably not doing anything remotely serious.

With a sport coat or blazer and odd trousers wear (I know there are some strict traditionalists who will take me to task for this):
Monk Straps
Boots (ankle/Beatle or lace up chukkas)
Belgian Shoes

The general rule is: the heavier the fabric of your trouser, the heavier looking your shoe can be. A severely tapered leg will call for a longer, sleeker shoe with a thinner sole.

With a suit wear:
Monk Straps (the informal choice)
Captoes (a safe choice. Wear brown with just about anything. There are those who argue against brown with navy. If it is a dark enough brown, I don’t think it matters. Black shoes go with everything but possibly brown suits. And if you are wearing black, they are required.)
Boots (a little informal depending on the boot and very John Steed.)

With formal wear:
Formal slippers, Opera pumps or patent lace-ups. You may wear highly polished un-ornamented black oxfords with a sleek and thin waist and sole. Cary Grant was photographed in polished penny loafers and a dinner jacket. He was Cary Grant. We are not.

Thanks to Nate for the idea!

7 thoughts on “Choose… Shoes

  1. You’re very welcome for the idea. I do disagree with your “any shoes” with jeans philosophy. Although it may depend on the pair of jeans.

    Every day I am striving to reach Cary Grant status…

  2. Interesting–lots of food for thought. I’d say that the shade of brown that best goes with navy depends on the shade of navy. Oxblood and burgundy can pair beautifully with navy.

    The formal slippers with your dinner jacket are for at-home events only, of course.

    You are correct when you say that men over 30 (or so) should generally avoid athletic shoes when not engaged in such activities, though your list of old-style shoes would be the only appropriate ones for very casual wear, like with shorts.

    You don’t care for wingtips?

  3. I am well over 30. However I still wear a pair of classic all white K-Swiss with my shorts.

  4. hmmm…chukkas with shorts? It might be my own East Coast dialect issue as, here near NYC, chukkas equal what is termed “desert boots” which end above the ankles. Is it possible you are referrring to bucks, white or sand-colored? Ubiquitous with shorts, sans socks!

  5. “Formal, in my day, meant dinner clothes — a tuxedo. For my grandfather it would have meant white tie and tails. Semi-formal was what we now call — erroneously if my eyes don’t deceive me — “business dress.””

    We used to distinguish formal as “dinner jacket”, (aka tuxedo), and informal – a suit, (aka “business dress”). Fraught with possibilities of getting it wrong, but of course there was a “code”, which no longer exists. At all.

    “It used to be said that you could tell a gentleman by his shoes.”

    I still think this is the most important piece of “kit”. Get these right, and everything else is acceptable. Slightly unrelated, have you been following the stories of Prince Charles’s shoes from Lobb – made about 30 years ago from his lasts, and still looking PDG, patch job an’ all?

  6. Hi Trish, nope I meant chukkas/desert boots. I usually wear them with a pair of Ghurka shorts though. With the standard flat front khaki shorts, I will wear my white bucks — I have them on now, albeit with a pair of linen and silk khakis.

    Columnist, hadn’t heard the story. But I’ve been pressed for time and not out surfing a lot recently.

    George, keep fighting the good fight. Even on your own time.

    Brent, full brogues are wingtips. I think I mentioned that in the post. But generally they’re not my favourite look although I have a stout pair of wingtip storm shoes in cordovan that look great with tweeds, cords and cavalry twill, etc. I think of them as a bit less formal and so prefer them in brown or suede (that pair of Church’s in the photo for example.)

    Nate, keep striving. I am, too. I do have a photo of CG in a jean jacket, blue jeans and boots inspecting some property later in his life… Even he, as is well known, wanted to be CG.

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