We have spoken recently about our love for all things minimalist. We have also extolled the virtues of a simple, crisp white T-shirt. But we also know that life is short. And if we can’t go to town with what we wear – figuratively and literally – then we’d be in danger of being more than a little bit dull. Which brings us to this week’s style question, put to us by one reader on Instagram. How can we wear a silly shirt and get away with it? How do we work flamboyance into our wardrobes? Fashion expert Mr Stephen Doig has the answers.

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What are some good ways to break into wearing crazy shirts?

@the.superior.baker, via Instagram

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There are certain words that can set the sartorially inclined fellow’s teeth on edge – “snazzy”, “wacky” and “jazzy” are three of them. A “jazzy” shirt calls to mind school discos, with Mum flattening your hair down with her spit-spackled hand and telling you that you look handsome in your jazzy shirt, because it was something a touch “bells and whistles” beyond the workaday norm. A snazzy shirt is the stuff of children’s TV; if you’re British, you’ll recall 1980s kids’ entertainer Mr Timmy Mallett in a series of lurid-hued, garish patterned shirts. It can hint at specially-themed office days or frat-boy, spring-break high jinks. A wildly printed, bold-coloured shirt is the confluence where novelty and style meets, and it’s a tricky path to navigate. But fashion is on the case.

Ms Miuccia Prada, who frequently tackles tropes of bad taste, has taken garish horror themes and flashy florals and applied them to boxy short-sleeved shirts for AW19. Likewise, everyone from Gucci and Versace to J.Crew has created shirts with eye-popping patterns, splashy prints and tropical colours. Part of the issue with bold shirts is that the guy who is accustomed to more classic varieties can tend to wear them in a self-conscious kind of way, as if he’s on a themed dress-up day at work. The first step, without sounding like a Goop life therapist, is owning your OTT shirt.

You can do so safe in the knowledge that, despite whatever vivid print you choose, a shirt is a shirt is a shirt. The design will always adhere to a certain formality and convention. Collars are inherently formal, and the shape varies very little. Decide if you want to opt for a fashion stance with your shirt. Certain brands cut the shapes slightly differently to add a more directional take, for example Prada’s short-sleeved shirts are deliberately boxy, cropped and floating away from the body, Gucci creates soft-fit silk shirts designed to be left untucked and breezy-looking. This adds a high-fashion spin to temper the novelty value of a high-octane print.

Similarly, balance the rest of your outfit to offset the boldness of the shirt – a dark wash of jeans, with love-worn sneakers, will treat it in a more casual, low-key way, likewise slouchy trousers. Don a crisp white T-shirt underneath to offset the spangles and showmanship, or, better yet, wear it with a sleek, lightweight black rollneck to act as a salve.

And if formal attire is your particular go-to, try pairing a razzmatazz shirt with a sleek suit; one of Versace’s wildly opulent silk shirts underneath a black suit jacket can provide a seductive hint of personality to offset the uniformity of classic tailoring. Your shirt might have more exuberance than normal, but how you wear it is the thin line between swaggering showman and CBeebies presenter.