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.
Chukka boots (desert boots)
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):
Boots (ankle/Beatle or lace up chukkas)
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!