Introduction
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.
Matt Allinson
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Great article. Absolutely spot on. Hadn’t considered black shirts recently but will now.
My prefference is for colour – I wear my burgendy, dark blue, and dark green shirts from September to March without fail. Either as a useful extra layer or on their own they are so veratile.
One question – Do you really believe in grey as an alternative to light blueshirts with a suit? My feeling is they just look a bit dirty – like a white shirt put through a colour wash and not smart enough for the office. Am I not forward thinking enough.
hahaha well it depends on the grey you get. I tend to go with a mid-grey about two shades lighter than charcoal. That way people can tell it’s a grey shirt and not a dirty white one. And if you pair it with dark colours such as navy, olive or black it becomes even more obviously grey. And yes, 100% a great alternative to blue.
should have mentioned never to wear a black shirt with a tie as your shirt should never be darker than your tie
agreed. I’ve covered it in great length in earlier basic articles though.
Never wear a black shirt to a bar or club unless you want to look like the staff
I always wear black shirts to go out as well as wearing a bow tie with it of all different colours. Never been asked if I was staff and always get told how good it looks. Plus I don’t have to worry about any embarrassing stains that might have appeared by the end of the night because nothing shows. Think these theories are more myth than fact.
great combos, i’ve tried the burgundy, navy brown tie look, and it was a smash!
i wear black shirts in bars sometimes and ive never been asked if i’m collecting glasses either. i’m guessing whoever comment 3 is referring to doesn’t wear them properly or is buying the wrong shirts.
Really need to get my hands on some dress shirts. Not too keen on wearing black dress shirts but navy and khaki is something i can see myself in. Great article!
Great article. I’ve been looking for bottle green shirts for a while now, but I can’t find any nice ones – they all tend to be a bit to camo coloured. Any suggestions anyone?
Black shirts are a never for me.
Really interesting options here, and I agree that burgundy shirt paired with a navy suit and brown tie is a winner. However, I think only women can make the dodgy pairing of black and navy blue work, and even this is only when the textures are different.
I know what you mean mate. I probably should have expanded on it a bit more (or maybe I’ll save it for an article) but I think navy and black can work together but it’s all about balance. Never pair navy and black together on your chest because it creates a blackhole effect like a shirt and tie. However, accessories are a go like braces, watches, shoes and belts etc. A black shirt with a navy suit can look really good for an evening but only with the jacket on, as soon as the jackets it off you look a little bit too two-tone. And yes, texture can be a real help like a navy tweed suit and an oxford cloth black button down.
I will defo be on a hunt for a light grey shirt in the post-Xmas sales, readying my self for NYE.
I’ll probably match it with a black (or black with white spots) bow-tie and a burgundy velvet blazer and black chinos.
I’ll definitely look cool :)
the only risk with grey shirts imo is looking like a mormon or a priest from one of the marginalised subsections of christianity
I have seen people wearing black shirts with ties and they look good to me. It’s just me is it?
i see alot of people wearing chino trousers and then bending them in at the end and i think its hot coz fashion beans teaches us alot so big up to fashion beans coz am a trend setter as well but no one can keep up lol
good article
I find it reassuring that you went to Leeds, i’ve lived there at uni for a few years and i’m sure you are familiar with the waxed/steroid all saints/aqua clones that that place breeds.