Smart Trousers


If there is one thing, in the gentle naivety of my youth, which I never believed I would say it’s this: I am bored of wearing jeans. I still wear denim. Mostly slim fit and skinny denim; very fashion-forward stuff which keeps my outfits from looking too pompous. I have this belief that fashionable denim keeps even the most establishment of outfits as fresh as ever. But denim is not something that now, I wish to wear day in, day out. I will always buy it, for me it is indispensable, but I feel more excitement for other items now; grey flannel trousers, black skinny trousers, Prince of Wales check Oxford bags. There is so much variety in terms of smart-casual trousers, and this autumn and winter, there has never been a better time to fill your drawers with non-denim pants.

A couple of years ago, I was warmly ensconced with a filthy martini and some young woman in a bar who gave me some interesting, albeit affronting advice. She told me that the trousers I was wearing were ‘Smart but not sexy’. ‘Jeans are just so much sexier’ she said. I didn’t agree with her, and quite frankly, despite a little immediate soreness, I didn’t care. Trousers were certainly not en vogue, unless you happened to be wearing them as part of a suit, and some women I have encountered have judged male sartorial sex appeal on the popularity of the clothing. Individualism back then was not really all that appealing.

Two years and a Pete Doherty later and Individualism is the new rock and roll pastime. Mocking the nouveau Mods, shops such as TopMan were piled high with every kind of vintage knock-off and badge of eccentricity going; waistcoats, window checks, tie-pins, fedoras and flat-caps. It was, and still is, a period in which Period was in. Riding in on the wave of heritage came trousers; and they were not combats.

Here are a few suggestions for those who believe their lower-half is in need of a little tailoring.

Check trousers

Check trousers are a quirky item for the wardrobe. They are not simple, and fashion is temperamental about their charms. However, a classic check in brown or grey will look sophisticated and stylish in the years to come. For different looks, go for two types of trouser; perhaps a brown check pair of slim fit or skinny fit for more on-trend, daring looks and a pair of wide-legged grey check trousers for wearing with looser fitting cardigans and jumpers.

Nailhead, tooth and other patterns    

Smaller patterns also look fantastic and though they are very much daytime wear, are extremely versatile. A small houndstooth check or large nailhead pattern can look fantastic when worn with a velvet blazer. With this style of trouser, Oxford bag cuts with turn ups can look great, although I believe slimmer versions of houndstooth checks, for example, are more appropriate.

Grey flannel

Grey flannel is classically appealing and an evergreen style fabric and it’s ridiculously versatile; Audrey Hepburn framed a picture of Fred Astaire, whom she adored, in his favourite grey flannel. The trousers look fantastic with casual jumpers and smart, dark jackets and go wonderfully well with brown or black shoes. I would favour a narrower leg with grey flannel as they are more likely to be used for smarter occasions than more casual ones. Adding turn ups is a nod to tradition as this is how Astaire himself wore them.

Evening trousers

Not just for formal occasions, evening trousers are suitable for cocktails or dinner with friends; they’re certainly edging towards ‘dandy’ in style, but who cares? Wear them with or without satin or velvet trim, keep them slim and couple with smart patent loafers (as pictured) and perhaps a cashmere turtle neck.


Winston Chesterfield is an amateur composer, fashion blogger, trained lawyer and style aficionado. He lives in Westminster, London and blogs at