How to look crazy through fashion.

Why to Dress Like a Lunatic—and How

Why to Dress Like a Lunatic—and How

Notes from the fashion apocalypse.
Sept. 9 2014 1:00 PM

The Art of Dressing Like a Lunatic

It’s what’s in for fall.

Courtesy of Simon Doonan
Simon shows how it’s done.

Courtesy of Simon Doonan

Last week I dashed into my man-closet and assembled an impromptu promenading outfit. Some people are addicted to SoulCycle; with me it’s promenading. I am constantly scanning the horizon for new and better promenades. If you spot any good ones, please let me know.

Simon Doonan Simon Doonan

Simon Doonan is an author, fashion commentator, and creative ambassador for Barneys New York.

Before exiting my apartment, I took inventory in my fashion looking glass. My outfit comprised the following:

• A snazzily printed pair of swim shorts by Mr. Turk. (The boiling temperature disinclined me toward trousers.)

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• A Liberty floral button-down Western shirt. (All my shirts are flowery Western shirts, stitched in Houston by seamstresses at the historic house of Hamilton, founded in 1883.)

• A Walter White–ish Florsheim huarache. (I think it’s so important to wear well-ventilated shoes at this time of year, don’t you?)

• A striped Barneys sock. (My ankles are decorated with broken veins—I am starting to wonder if my ankles are not secret gin-tipplers—so going sockless is a nonstarter.)

• A cheap cowboy hat I purchased from a street vendor. (I have already had two pre-cancers removed from my head, so I make a point of not leaving the house without a substantial chapeau.)

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• A monogrammed Goyard man-bag.

• And, last but not least, a pair of oversize Oliver Goldsmith shades. (They are a replica of the design worn by Michael Caine in 1968, named the Matador.)

As soon as I hit the street, I noticed that people were reacting to me in a freaky and unfamiliar way. Very unfamiliar. While the light mockery that might greet an outré or trendy high-fashion outfit is more than familiar to me, this particular reaction was unprecedented. People were cringing. One lady crossed the street. Couples were clocking me and then anxiously nudging each other. Fearful gazes were nervously downcast. Like a volatile despot, I felt the surge of glee that comes from knowing you have the power to scare the crap out of complete strangers. Suddenly it hit me. By dressing like an insane person, I was getting something I’d never had before: some respect.

As autumn approaches, hordes of people are begging me for fashion advice. Actually that’s not entirely true. It was three people. Maybe two. Anyway, based on my recent epiphany, I have been telling my advice seekers—both of them—that fall is all about dressing as if you are ever so slightly unhinged. A soupçon of gaga. Just a tad batty. Be creative. By dressing like a nut job, you too will get the respect you so richly deserve.

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How best to achieve an intimidatingly loony look? Here are the pointers I shared with my two pupils.

Firstly, know that it does not take much to terrify people and have them eating out of your hand. Dressing like a mental patient is about tweaking a micro-convention or two. Bust the arm off your spectacles and replace it with a worn-out toothbrush, and you will see exactly what I mean. All Little Edie Bouvier had to do was tie a sweater around her head and turn her skirt upside down. All Celine Dion had to do was wear a backward jacket.

Revolving or inverting your garments is one way to get results. Improbable layering is another. In our society, convention dictates that certain things are worn over certain other things. Cardigans are worn over blouses, as sure as day follows night. Deviating from these precepts is a low-cost way of looking bonkers. Skeptical? Try wearing your black brassiere on top of your canary-yellow shantung brunch coat and get back to me.

Now let’s address the topic of pattern, and, while we’re at it, allow me to get all anthropological. There are two groups of people on the planet who love bold prints: West Africans and myself. While the rest of the planet has a shockingly low tolerance for bold pattern, me in my florals and the West Africans swathed in their legendary Dutch wax prints are digging it. Learn from our example. If you want to get respect, ditch your solid gray Hugo Boss business suit and throw on a caftan printed with early-’90s cellphones.

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Next: temperature obliviousness. Nothing says “Watch out, ’cause I’ve lost my mind” quite like a woolly cape in summer or, conversely, a dental floss thong in winter. If you want to rattle the cage of the status quo, then simply demonstrate a willful indifference to the climate.

Finally, let’s discuss your crowning glory. To generate maximum luni-respect, wear a hat that has nothing to do with your profession. Let me clarify by citing the moment in Nathaniel West’s Day of the Locust when protagonist Tod Hackett becomes mesmerized by the surreal fashion choices on Hollywood Boulevard:

The fat lady in the yachting cap was going shopping, not boating; the man in the Norfolk jacket and Tyrolean hat was returning not from a mountain, but an insurance office; and the girl in slacks and sneaks with a bandanna around her head had just left a switchboard, not a tennis court.

Et voila! Situation-inappropriate headgear can always be counted upon to generate a nasty frisson.

As you can see, garnering respect requires, paradoxically, a thoughtful and subtle approach. Do not overdo it. Clowny, street-theater antics—painting yourself gold or riding a monocycle whilst wearing Edwardian attire—will engender contempt rather than respect. And never involve animals. Plonking an iguana on your head or a parakeet on your shoulder just means you are annoying and/or you live in Florida. Trust me. When promenading I run into those kinds of people all the time.