The 7 Deadly Sartorial Sins

The 7 Deadly Sartorial Sins

“It’s all about breaking the rules!” Or so many a style pundit will tell you.

And indeed, if you’re Gianni Agnelli – the late Italian industrialist, jet set figurehead, and undisputed “Rake of The Riviera –  you can make crazy transgressions from protocol like wearing your watch over your shirt cuff. Us ordinary mortals, though, need to play the style game a little differently.

Yes, more confident players can dabble with some of the rules, some of the time – by wearing shoes of a lighter hue than one’s trousers, for example. But there are some style felonies which are going to see a 100-decibel shrill emanate from where the referee’s standing.

And, like the worst human offenses outlined in biblical scripture, most Deadly Sartorial Sins fall under one of seven single-word categories.


So, we start with something Pope Gregory identified and outlawed - sloth. Whereas the prim pontiff was referring to spiritual laziness, though, our pet peeve here is with sticking to go-to ensembles instead of constructing a wardrobe in which each garment has a bit part in multiple permutations.

Now, there's nothing wrong with a classic pairing, particularly if it's for a formal occasion, but why not mix it up a bit from time to time? 

For example: our blue mohair suit could be teamed up with this plaid flannel shirt in blue and burgundy, this Venezia belt in cognac, and these brown suede loafers – great look! Alternatively, pair your suit with a light pink linen dress shirt and orange silk medallion necktie. Replace the trousers with light gray Tasmanians and slip on these brown medallion Oxfords. Now your outfit has an entirely different – but equally slick – vibe!

In other words, see your clothes less like a restaurant menu, and more like the list of ingredients behind it.


Shirts collars draped over lapels (unless you’re Al Pacino in Scarface or Brad Pitt in Fight Club); untucked shirt with a suit (unless you’re Robert Pattinson and on a red carpet); wearing your tie loose or undone (unless it’s a bow tie, you’re playing James Bond, and you’re contractually banned from wearing it done up – and Pierce Brosnan was all three in 1999’s The Thomas Crown Affair).

All of these come across as sartorial entropy. The Italians might gush about sprezzatura, or effortless flair; they don’t have, or need, a word for effortless scruffiness though.


This refers to apathy towards rules that seem, at face value, meaningless. These rules exist simply because they do. Fastening the top button - and the top button only - on a two-button sports jacket (the middle one if it has three), is a great example of a rule you shouldn't disregard. Elsewhere: the ‘Full Windsor’, or double knot, is too try-hard, in our opinion. Stick to four-in-hand with a natural, incidental dimple.

Meanwhile, some fashion cliches – white socks and double-deniming (for men) being faux pas – are cliches because they’re true. Never buck convention just for the hell of it.


Fashion and style are as different as infatuation and love. One is fleeting, superficial, banal; the other is permanent, profound, and vastly more meaningful.

So think long-term. A classic wardrobe that fights against the banality of clothing being either “in” or “out” of consensual favor right now is much healthier than allowing the whims of fashion to dictate what you wear. It’s no coincidence that clothes designed to be trendy, or in vogue, tend to lack the fabric or build quality to last.


The sartorial rogue’s gallery is replete with garish photos of men who have tried too hard to be different: many of them wearing fat checks on their sports coats with bold stripes emblazoned on the shirt beneath – or vice versa.

That said, a little flamboyance goes a long way: British designer Jeremy Hackett once told me, “A simple blue and white stripe shirt worn with a classic polka dot tie is a very English custom, and mixing stripes, spots and checks works very well.”

Garments such as our grey gun check sport coat offer a discreet, subdued check which allows greater flamboyance in other garments.


Paradoxically enough, too much similarity between two garments can jar as much as the big stripes/big checks horror show: hence the double-denim conundrum. The worst offender here – by a country mile – is the matching tie and pocket square combo.

Think of it like wine pairing: an elegant contrast acts like one flavor cutting through, and balancing out, the other.


We bookend this sermon with another offence Pope Gregory found abhorrent: here, though, we refer to overt sartorial conspicuousness. We’ve all seen the self-proclaimed Pitti Peacocks at the trade show in Florence twice each year – often on the sidewalks, holding newspapers aloft to hail imaginary taxis (a pose they hope will attract the attentions of the style snappers present).

Forced eccentricity is perhaps the deadliest of all sartorial sins. Again, it comes back to that Italian concept of sprezzatura: grabbing attention from sartorially discerning observers without looking like it was ever your intention to do so. This is the dignified approach to dressing, and one that we continually aim to facilitate here at Anatoly's.

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