Many men treat shirts and polos as summer clothing, pushing them to the back of the wardrobe once the clocks go back. That’s a waste, as you can easily make your clothes work all year round with Ben Sherman, a British label whose shirts have been worn under jumpers and jackets for over sixty years. When you’re wrapped up against the cold, the collar is often the only visible part of your outfit, so it pays to get it right.
This guide looks at how to integrate classic Ben Sherman shirts and polo shirts into a winter wardrobe, from layering under knitwear to choosing colours and fabrics that suit shorter, greyer days.
Why Ben Sherman works in the colder months
Ben Sherman started in Brighton in 1963, taking the American button-down shirt and giving it a British slant. The shirts were quickly adopted by the mod scene, where they were worn buttoned up under V-neck jumpers and parkas. They were built to be layered from the start.
The button-down collar is the practical detail here. Because the collar points are fastened to the shirt, they stay flat under a crew-neck jumper or a zipped jacket instead of curling or disappearing. A soft spread collar can look untidy under knitwear by mid-morning, while a button-down holds its shape all day.
Layering the Oxford shirt
The Oxford shirt is the most useful Ben Sherman piece you can own for winter. The cloth is heavier and more textured than a poplin dress shirt, so it looks right with chunky knitwear and casual jackets.
The simplest approach is a crew-neck jumper over a buttoned Oxford, with just the collar showing. Merino or lambswool keeps the bulk down so the shirt sits flat underneath. If you’d prefer a V-neck, leave the top button undone and let the collar points sit inside the neckline.
For weekends, wear the Oxford open over a plain T-shirt or long-sleeve top, with an overshirt or quilted gilet on top. The shirt then acts as a mid-layer you can take off indoors. Indoors, rolling the sleeves once or twice gives a more relaxed look.
Fit matters more when you layer. A shirt that’s too full in the body will balloon under a jumper, so look for a slim or tailored cut if you plan to wear it under knitwear most of the time.
The polo shirt in winter
A short-sleeve piqué polo on its own is a summer look, but polos earn their place in winter once you start layering them. The tipped collar on a classic Ben Sherman polo is a nice detail to show off at the neckline of a jumper or jacket.
The long-sleeve polo is the easiest way in. It has the same collar and placket as the short-sleeve version, with enough coverage to wear under a cardigan, a zip-through knit or a Harrington jacket. Knitted polos go a step further: they are warm enough to wear as the main layer on milder days, with a coat over the top when the temperature drops.
If you want to wear a short-sleeve polo through winter, treat it as a base layer. Put it under a crew-neck jumper with the collar out, or under an overshirt left open. Either way, the polo should be close-fitting, since extra fabric around the body’ll show through the layer above.
It’s worth building up a few colours. Browsing a range of men’s polo shirts with winter in mind usually means picking darker, richer shades than you would for summer, which leads on to the next point.
Colour, pattern and fabric
Winter light is flat and grey, and pale pastels can look washed out against it. Navy, bottle green, burgundy and charcoal all work well, and they sit comfortably alongside the browns and greys of most winter coats. White and light blue Oxfords are still worth having, as they lift a dark jumper and stop an outfit looking heavy.
Pattern is where Ben Sherman’s always been strong. A gingham or tartan check shirt under a plain navy or grey jumper gives you a little something at the collar and cuffs without being loud. If the shirt’s patterned, keep the knitwear plain, and the reverse applies if you’re wearing a cable knit or Fair Isle.
Fabric weight makes a real difference to comfort. Brushed cotton and flannel shirts hold warmth better than standard cotton and feel softer against the skin on cold mornings. Corduroy shirts also work, though they’re better as an overshirt than as something to wear under a jumper.
Outerwear, trousers and footwear
The coat you choose should suit the shirt underneath. A fishtail parka or a wool peacoat over an Oxford and jumper is a nod to the mod look Ben Sherman grew out of, and it still works for everyday wear. For something lighter on dry days, a Harrington jacket over a long-sleeve polo is hard to beat. A padded or quilted jacket suits a more casual outfit built around a check shirt and an overshirt.
Dark denim is the obvious partner for both shirts and polos, and a slim, straight leg keeps the proportions right when you’ve several layers on top. Chinos in stone, olive or navy smarten things up, while cords add texture and a bit of extra warmth.
Finish with footwear that can handle wet pavements. Leather Chelsea boots or Derby shoes in brown or black suit a shirt-and-knit outfit. Clean white trainers can work with a polo and denim, but leather is the more practical choice through the wettest months.
Putting it all together
A winter wardrobe built around Ben Sherman shirts and polos doesn’t need many pieces. Two or three Oxfords in plain colours, a check shirt in brushed cotton and a long-sleeve or knitted polo will cover most situations once you add a couple of good jumpers and a coat. If you’re starting from scratch, a navy Oxford and a long-sleeve polo in a dark shade are the two pieces likely to get the most wear between now and March.
