Struggling with the capricious weather? Flexible, smart layering makes for the easiest entry into winter.

Fashion is seasonal. Reality isn’t. This becomes especially noticeable in these transitional weeks as we plough towards winter. With a daily weather outlook that’s roughly as reliable as a tabloid horoscope, you need to hedge your bets. This means brushing up on the art of layering. To do it right, you need to be willing to throw disparate elements together, while keeping an eye on colour. If you’re wearing all one shade, you risk being dubbed Mr Blue by your co-workers. Add one too many, and the office wag will be asking how was your audition for Joseph and the Amazing Technicolor Dreamcoat. Limit yourself to two shades that go well together – for example, blue and grey – and you’ll be fine.

To put the following layered looks through their paces, we took a group of young gentlemen to the shoreline of West Wittering beach in West Sussex. However, the outfits work in many a blustery location worldwide, from the Pacific Northwest (home to heatwaves and downpours in equal measure, as well as some great masters of layering) to New England.

In functional terms, layering allows you to adapt to a changing environment by shedding or adding pieces as you see fit. It’s therefore key to combine layers so that they are easily removable, a technique demonstrated by Mr Max Townsend (above), who is currently reading ancient history at the University of Bristol. A buttoned cardigan is a convenient inner layer that can be quickly dispensed with in case of sudden sun. This winter’s trend of oversized coats offers ample room for layers beneath, and can be easily shrugged off in a moment, should the need arise.

Layering well is a chance to be creative with your look. This is probably why so many of pop culture’s most revered rebels, though perhaps lacking judgment in their personal lives, were great at layering, from Mr Jean-Michel Basquiat (big coat, multiple shirts, sweater, tie worn as scarf) to Aberdeen, Washington’s Mr Kurt Cobain (fluffy cardigan, plaid shirt, tee). Clearly, given this historic pedigree, a layered look that seems a little thrown together is no bad thing. Mr Henry Pedro-Wright (above), an art lover from Barnes, London, gets the attitude right by adding an element of the unexpected to his outfit, wearing a military-inspired bomber jacket under his more formal cashmere-blend coat.

The easiest way to harmonise colours is to pick two and stick with them, working with your main colour by combining shades of varying intensity, and using the second as an accent. This approach is illustrated (above) by graphic designer Mr Nick Offord, who offsets his navy layers with a light-blue rollneck sweater. Neutral colours such as navy, black and grey are the easiest to combine, but, thanks to the panoply of textured pieces proposed by designers this season, they needn’t be dull – pairing fine with chunky and rough with smooth gives even the simplest hue a little depth.

A layered look should, above all, seem casual and comfortable and the tactile, pliant fabrics of the season are perfectly pitched to carry this attitude off. The MP di Massimo Piombo coat worn by Mr Jake Lucas (above), a guitarist and event promoter, incorporates super-soft baby-alpaca fibres for a teddy bear-like finish, while his Marc by Marc Jacobs sweatpants offer a relaxed alternative to the classic wool trouser. A pair of leather boots or a beanie (albeit a cashmere one from The Elder Statesman) add some rugged details.

If you need any persuading that it’s not just fine, but advisable to wear both a coat and a blazer in your layered look, seek out a copy of Mr Gus Van Sant’s 1991 movie My Own Private Idaho, in which Mr River Phoenix seldom braves the streets of Portland and Seattle without at least two pieces of outerwear. Model and PR man Alex Dunstan (above) keeps the look comfortable by opting for a wool- and cashmere-blend coat with roomy dropped shoulders from Burberry Prorsum, and a soft, unstructured Gucci shearling jacket. Naturally, shoulder padding should be avoided here, so that you retain the use of your arms. Teen idol status is not guaranteed, but you will most definitely keep toasty.

The neckline is a great place to show off a little with your layering expertise as it’s where all the layers come together very visibly – and practically speaking it’s also an area that gets particularly chilly in strong winds. Combining different collar types ensures you’re covered on both fronts, whether you go for a shawl-collar cardigan for under your notch-lapel overcoat, as worn by Mr Greg Francis (above), a student of menswear design, or a fine merino turtleneck under a crew- or V-neck sweater. As there’s always a lot going on in a layered look, darker colours tend to work better here, making sure the face is picked out rather than swallowed up by the weight of the outfit.