When it comes to shirts, I think a lot of guys stick to the basics. Firstly, they view a shirt as something to wear when you want to dress up and look smart. Secondly, they only stick to the holy trinity – white, blue and pink. Both of these things are fine and will see you through many situations. In fact, as part of a basic wardrobe, white, light blue and pink Oxford cloth shirts will see you through pretty much any sartorial dilemma you can think of.

However, what happens when you want to push things forward? Where do you go from there?

Now that we’re in the throws of winter and Christmas is nearly upon us, why not start with some shirts that are more appropriate for the colder months? By this I mean look for colours that are in darker tones and remind you of the season you are in.

The Black Dress Shirt

Your first port of call should be a black dress shirt. In the colder months you will find this to be one of your most versatile shirts and it was pretty much invented for the night. So don’t even think about wearing this with your suit to work! But wearing it with your suit out in the evening? Oh, yes. Very much so.

Try to pair it with other monochromatic colours such as grey and navy and you can’t go wrong. If you are going with the suit, leave the tie at home and loosen a few buttons. I would even recommend taking off the belt (because your trousers should fit you properly enough to not require one) and switching to a more comfortable shoe in black – such as a loafer. Think Ryan Gosling in Crazy, Stupid Love in his grey three piece suit, black shirt and matching accessories.

If a suit doesn’t quite suit your personal style, then why not pair it with other versatile pieces like v-neck jumpers, cardigans or denim jackets?

Grey & Navy

From here, you should then branch out into the other monotones – grey and navy. You will find a navy shirt to be just as versatile as your black one, and it looks great paired with earthy colours such as brown and dark greens. For Sunday afternoon meals with friends I often wear my navy shirt with olive chinos, a charcoal knitted tie and some casual boots as an easy go-to.

As for the grey shirt, think of it as your new alternative to the light blue shirt – everything it can do, the grey does better. Aim for a mid grey shirt and pair it tonally with other greys or with other colours for the best results.

Coloured Shirts

Finally, all that’s left to do is get adventurous! Burgundy is a key colour of the season and looks great when paired with a navy suit/blazer and anchored with a brown tie. It also works well casually with a pair of jeans or beige chinos and a chunky cardigan thrown over – so why not pick one up?

Another great colour to add to your wardrobe is khaki or camel. It’s a colour that has been making a comeback on the runways the last couple of years but why let it just belong to coats, jackets and chinos? Pick up a shirt in this colour and pair it with monochromatic tones such as navy, grey and black to really liven up whatever outfit you’re wearing.

With the addition of these five winter shirt choices you will be able to breathe new life into your basics wardrobe and hopefully see you through to when the sun reappears. And part 2 of upgrading your shirt collection will be ready next week to help you out when it does.