When I first got started in menswear, even before I studied textiles at university, I had quite a straightforward approach to thinking about shirts. In my mind, all shirts were considered four-season pieces, and it was a simple matter of stocking up on a few in a spectrum of whites, light blues, and Bengal stripes.

This is in no way wrong if you’re building a working wardrobe – in fact, this is an approach I’d encourage everyone to start with. However, most people (including myself) sometimes forget that beyond being a foundation stone in your wardrobe, shirts can also be a great tool for self-expression, in seasonal cloths that will be both aesthetically and functionally more pleasing during the fall-winter or spring and summer months. As much as a fine poplin striped shirt works as a wardrobe staple for business, it can – in my own experience – be quite challenging to dress down with denim and knitwear.

If we start with a winter shirt’s looks, I would focus on texture first and foremost. Autumnal shirts will be combined with rugged and often coarse fabrics such as tweed, cotton drill and denim, so a shirt with a smooth handle or else a gently brushed finish offers a softer note that will contrast with your jeans and sports coats. The Thomas Mason Balmoral collection; a range of beautifully woven cotton and cashmere blend twills, is ideally suited to the cooler months. The flannel finish really elevates a cold-weather look. Try one in a soft powder blue and combine with bold checked jacket or shearling coat.

If you’re up for experimenting with patterns, there are some lovely fine checks and pied-de-poules in Balmoral, too. These add some visual depth to the fabric’s soft texture, and are still easy to combine with larger patterns in your jacket or tie. Thanks to the informal nature of these fabrics, I prefer to wear brushed shirts with button-down collars rather than a smarter spread-collar design. In terms of colour, I think the cooler months offer the chance to wear darker shades more so than in summer. A dark indigo shirt in a soft denim quality (see Thomas Mason’s Victoria Denim or Brisbane qualities) under a navy blazer in a similar shade, offers a sharp tonal look that plays particularly well in the winter.

Other colours I’ve come to love during the autumn season are cream and warm shades of light dove grey. They are both light enough to create the necessary contrast against navy or charcoal, but softer than the clinical whites and surprisingly versatile when worn against taupe and brown. Try a cream flannel shirt under a tweed jacket for something understated and far more sophisticated than conventional white or light blue.

For years, my personal style was heavily influenced by formal suits, jackets and ties, but over the last couple of years I’ve shifted towards a more dynamic and diverse mix of formal and casual pieces. Today, I layer shirts, knits, and baseball caps with classic sports coats or suede jackets in a way I rarely used to. I’d be lying if I said that this wasn’t influenced by the global shift in trends we have seen in the last few seasons but it is a welcomed one nonetheless.

This new ‘hi-lo’ approach to shaping outfits in my wardrobe has opened a completely new path in my shirt collection whereby a heavier Oxford shirt is now a core staple that I wear with everything from faded denim jeans to flannel suits. These heavier fabrics are true icons in menswear history but can be painfully hot during the summer months so I’ve started to wear them almost exclusively for fall. With the historical connection to the Ivy League style, I tend to wear these shirts slightly fuller with a breast pocket and always a generous button-down collar. One of my favourite outfits consists of a pale yellow Oxford shirt worn with my navy club blazer and faded denim. To most people, this might feel like a summer look but the weight of the shirt’s fabric is the thing that makes a difference. Thomas Mason’s ‘American Oxford’ collection, which is a little heavier and more rugged than their classic and Royal Oxford cloths, is perfect for winter weather.

Another reason why I’ve started to enjoy a seasonal approach to shirting is of course that I get to experience the best of both worlds. While your traditional business shirts may be a comfortable uniform all-year-round, nothing beats the feeling of wearing something a little bit different when you’re off-duty. Just as I love to bring out my winter coats from deep within my closet each year, there is something rewarding in wearing certain shirts for a certain moment in time. In fact, writing this article reminded me of how much I look forward to once again bring out my linen shirts next summer. And I know I’ll be equally thrilled in October when I get to wear soft, heavy, and casual autumn shirts again too.