Style Rules: A Visual Guide To Ripping Them Up

A little sartorial transgression goes a long way, as the masterfully stylish attendees at Pitti Uomo 94 showed us. Here are a few tips on how to break the rules with confidence and skill.
Style Rules: A Visual Guide To Ripping Them Up
One of the most exasperating (and sadly commonplace) characters you’re likely to meet at Pitti Uomo is the smirking rules-lawyer. You know the type - the real-world-Redditor, here to educate the unwashed masses about which collar must be worn with what lapel, how many folds a tie must have before it can even be considered ‘real’, why the sanctity of sartorial style must never be compromised and so on. He’s obnoxious, he’s tiresome and, quite frankly, he makes getting dressed about as sexy as filing a tax return. These rules of sartorial style have their place, but style is a dynamic expression of individuality and thus can’t exist without rules being broken. And in the baking heat of the Florentine sun, taking traditional tailoring apart and dressing it down felt not only fun but positively essential. So how to do it exactly? Well firstly, consider that tailoring is a beautiful canvas, but a dress shirt and tie need not be the only materials you use on it. We are blessed today to live in an era where menswear has escaped its obsession with fit-über-alles and has embraced form, drape and silhouette, and that loucheness can happily extend well beyond the jacket and trouser.
Relaxed, wide-cut tailoring in darker hues will allow a crisp white cuban collar to stand out.
A patterned shirt will fuse suit separates nicely, while a plain polo will serve as the perfect underlayer for bold, monochrome tailoring.
Suit separates present an opportunity to play with proportions, matching a tailored jacket with loose-fitting chinos for a striking silhouette.
A smart denim shirt is a great way to dress down tailoring.
A smart knitted polo in a vibrant colour will complement tailored trousers nicely.
Mixing cuts, colours and materials is a surefire way to liven up your look, but tread carefully: it takes a special confidence to pull off a cobalt blue ruffled shirt with the top three buttons undone.
A pair of wide-leg Bermuda shorts can put a totally fresh spin on your overall silhouette when paired with a double-breasted jacket and T-shirt.
Opting for a boxier, unstructured fit can be stylish without seeming scruffy.
In terms of shirting, the early 1980s are a strong reference point. A pique polo makes a very smart shirting replacement indeed - elegant, pleasingly textural and incredibly breathable thanks to the cloth’s porous nature, it should be a summer staple - and the collar can work either under the lapel or popped out. The same can be said of this season’s most inescapable style, the camp collar shirt - team with your most casual tailoring for best results. One’s journey into Don Johnson territory can be completed with the unfairly maligned T-shirt-and-tailoring ensemble. With intelligent colour combination (ecru under navy perhaps, or mid blue under textured grey), it can be a pairing that both liberates and elevates.
A pair of sleek leather sandals will match the refinement of a tailored suit.
Espadrilles are a great way to play with colour, and will put a relaxed summery accent on your smart clothing.
The sneaker with tailored trouser combination is certainly nothing new, and remains both relevant and fashionable. For the more daring amongst you, a cropped trouser (or short, you devil!) and leather sandal can be a damnably stylish combination; this season saw many stalwart shoemakers (even the British) show sandals that were both smart and seasonally appropriate. And of course there’s our old friend the loafer - Belgian, ideally, though a suede penny or tassel will do just as well (and see you through almost any occasion). Regardless of style, loafers all have enough laid-back charm to look right at home when teamed with something as casual as a tee or short-sleeved polo.
Repurposing a tie as a belt is a maverick way to add a hint of playfulness to your suit trousers.
A pair of jeans and a bandana in a complementary dark blue will channel the more suave elements of Americana into your smart looks.
Dressing down doesn’t necessarily mean paring back either - the humble pocket square still very much has a place even on a jacket worn with a tee or a casual shirt. Better yet, team it with a bandana or neckerchief for a truly rakish summer ensemble. Clipped suspenders, too, can add a splash of colour and flair to an outfit, whether worn with tailored trousers or denim. Above all, don’t overthink it. We stand upon the precipice of a bold new sartorial frontier, so pour a drink, have a cigar and relax. Looking good can be fun.