How to Wear Bold Checks

Bold checked tailoring can be tricky to pull off, but when worn with the right pieces, is an indicator of a generous wardrobe and, most importantly, someone who’s confident in their style.
Mad Men characters Don Draper, Pete Campbell and Ken Cosgrove rock bold checks in Season 5 of the hit series set in 1960s New York.

My first dozen or so suits were all quite conservative in fabric, mostly solid greys and blues with the occasional subtle check or stripe, but working on Savile Row exposed me to some beautiful bold fabrics from the numerous West End cloth merchants. One of the most memorable I found was from Henry Lesser – a 13oz grey semi-milled worsted with an ecru pindot windowpane check ‘guarded’ with three lines of cherry red that could only have been woven in the 1970s. The sensible option would have been to choose a suit in a simple cut, but I wanted to match the ‘sportiness’ of the cloth in the style of the suit, so ordered a three-button hacking-style jacket with deep vents, a ticket pocket, a flap over the breast pocket, turn-back cuffs and cloth-covered buttons.

The suit was fabulous, but not without its controversy. The Yorkshire-based workshop that sewed it together disapproved of my styling choices and demanded that I remove most of the extra details or they would not make it. I agreed to their request on the telephone only to add them all back after the first fitting. When the owner of the factory discovered this, he called my manager saying that they would never make a suit for me again. I got around this by using a fake name on future commissions.

Bold checks contain clues of what they should be combined with, expressed in their colours, but it's important not to take this too far, and remember to add contrasting textures. A strong patterned sports jacket can be much easier to wear than a full suit, especially when worn with plain trousers. The concept of a ‘neutraliser’ in men’s style is referred to in the copy accompanying the wonderful fashion plates of Esquire in the 1930s and 1940s; the idea that a bold colour or pattern should be balanced with an article of clothing in a sombre, simple shade. Grey flannel trousers are the most useful ‘neutraliser’ and combine well with any bold jacket. Denim is also useful, but the sports-jacket-and-jeans thing never looks as cool as you’d hoped. The next time you’re tempted to wear jeans, wear flannels instead. Trust me.


February 2018


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