Top 5 Basic Men’s Fashion Must-Haves for Winter 2019

Nov 11, 2019

by Ian Dallimore

It wouldn’t be a winter article if I didn’t start out by complaining how bloody dark it is all the time now – but just because it’s dark, doesn’t mean you need retreat into your “comfies” and hibernate for the season. Winter presents an opportunity to be comfortable and look great all at the same time.

The Autumn/Winter season is my favourite when it comes to fashion, and I’ll make no secret of it. Layers, woollen accessories, boots, jeans, coats – I’m a sucker for the lot of it, and there’s so much you can do with it all. However, if you’re just dipping your proverbial toe into the world of men’s fashion for the first time, let’s give you a starting point. Something to kick off your fashion arsenal, bits you can pair with everything. A tutorial level. A walkthrough. 

It’s dangerous to go alone, so take these: 

Here’s my top 5 must-haves for any chap trying to make his way through the cold snap.

 1. Boots

Photo Credit: ASOS (Lace Up Boots; £55)

With winter comes treacherous roads, poor conditions, and a mighty need to wear thick socks.

Trainers just aren’t going to cut it here gents – nothing worse than the trek from tube to town in soggy Converse. Luckily for you, are just as keen as me on the Utility trend being exactly what you need through the winter.


Boots should be one of your go-to winter footwear choices. Robust enough to tackle the rougher weather, versatile enough to go with lots of different outfits, and after a couple miles of wearing-in, one of the most comfortable pairs of shoes you’ll own. 

Boots are a bit of an investment – and you get what you pay for. It’s not uncommon for some people to boast their Dr Martens last twenty-plus years when cared for. So if you’re able, don’t be scared to splash a little cash on these. If they’re treated right, they’ll last you many winters to come! Of course, leather will generally last a little longer and is the more classic choice, but suede will go a long way if you’re happy to give them a treatment spray once or twice a year whilst still looking great. I rock a pair of suede Dr Martens, and am into my third winter with them with barely a mark to see.

Photo: River Island (Brown suede Chelsea boots; £35)

Chunky soles are popular right now. Lace-up boots make great day-to-day, but if you want to sacrifice some of the robustness in favour of something a little smarter, look for some Chelsea-style boots (above). Can’t really go wrong with a black or a brown that will go with everything from jeans to checked trousers. During my research, I even found that boots can help you stand up straighter, as well as appear taller, making them great for a first date! They’re made for walking, so make sure that’s what they’ll do.

2. Long Coats

Photo Credit: BBC

We’ve all done it. We have, and don’t you deny it. We all watched a couple episodes of Peaky Blinders and took a quick browse for a long coat. Even GQ are still going on about longer coats

You may initially think “oh, a plain black coat isn’t very fun is it?” – but there’s more choice than you’d expect. Go patterned or textured, or go plain. Go coloured, go…camel? Burton have some great choices at reasonable prices right now, it’s definitely worth popping in with a friend to try some different styles on. 

See what sits well on your shoulders! Then throw them over a button-up shirt, layer them with a jumper too for the extra warmth, maybe even throw the flat cap on top for the full experience. Regardless, long coats will even look great with just a plain white tee underneath – it’s hard to go wrong with these, and will work just as well in the pub or over a blazer for more formal events. Gone are the days of popping the collar. Keep it smart and simple.

Remember, the classics are classic for a reason.

3. Knitwear 


There’s about as many varieties of knitwear as there are D&D Classes – and yes, you’re probably going to struggle just as much picking the right one for you. But once you’ve found it, you’ll stick to it and feel comfortable, with the odd dabble in something more unusual from time to time. 

So what’ll it be? V-neck, crew neck, turtleneck? Cashmere or cableknit? Chunky, slim, shawl or cardigan? As you can tell, we could be here some time. So this is where you take over.


This is where you can afford to be a little more brave – flamboyant almost. Autumn is a season for colour, so don’t be afraid to play with them. Mustard, olive, even a dusty pink can all be great choices away from the usual burgundy and navy jumpers. Something with texture is great to spice up a simple outfit of plain trousers and overcoat. 

Don’t be afraid of pink by the way fellas. Dusty pink and rose tones are really versatile and easy to pull off. Jumpers are easy. Rock them under a coat, or as your sole outerwear on milder days. Great for being cosy, but smart enough for down the pub with some jeans or trousers.

4. A Casual Blazer

Whilst frankly being a bit of a year-round essential, a casual blazer is much easier to add to an outfit during colder weather. You know, because layers (Shrek voice optional).

A casual blazer (or sport coat) is a little different from your formal suit jacket. It’ll be softer, less structured (it won’t have thick shoulder pads, if any at all), and doesn’t need your bottom half to match. There’s a number of different materials to pick from – lighter, summer-focused ones, such as linen or cotton being light enough to wear in the warmer weather (but you can make these work all year round). During the winter however, darker tones of wool, tweed or even jersey can work well with a lot of different outfits. 

You’re not looking for anything formal here, just another layer that is perhaps a little smarter. You can go with anything from a t-shirt, a jumper or even a hoodie underneath if you’re leaning on the more casual side of smart-casual. If you’re going loud with jumpers, tone it down and play it a little safer on the jacket to make it last longer. Muted tones to work with everything you throw at it – blacks, greys, navys.

A black jacket with black jeans and shoes/boots makes for a smart but contemporary look for dinners or parties. The same black jacket with blue jeans and clean trainers, works for something a little more classic and relaxed at the pub with friends. Swap the bottoms out for chinos in the summer. Throw in a scarf for the winter. You’ve got room to experiment and mix it up. Just make sure it fits! Not too long in the arms (You should be able to check your watch easily), and well fitted around the shoulders are key areas to look at when trying on blazers.

5. Jeans. Well-fitting Jeans.

If we’re talking basics, this is where basics start. I imagine, as a human being, you already own at least one pair of jeans – so I won’t teach you to suck eggs here. 

A well-fitting pair of jeans is important to any outfit, and will give you the chance to mix up a couple options – blue jeans, black jeans, etc. You’ll need to try a couple of different sources to get jeans that fit you well, in a style you like. For example, I’m 5’6 (so fairly short for a guy), but regularly train with heavy weights for powerlifting and rugby. My issue is that my legs are too short for the standard “short” leg length, but my thighs and arse are too big for my actual waist size. 

It’s taken me years to find jeans that work for me, in a style I like. I finally settled on the “Ollie” series from River Island – which I would heavily recommend to any guys looking for skinny jeans who are maybe a little thicker around the thighs. These are spray on skinny (great for the difference between my thighs and calves), stretchy fit (to get around my arse), and even come in “Extra short” (praise the lord). I still get issues with the crotch wearing out after about 18 months, but at £35 a pair (or £20 in the sale) it’s not a dealbreaker. I’ve also found success even in Primark – their skinny jeans have held their shape and fit me well for about 2 years now! Perfect for work or casual jeans.

If you’re a bigger guy, don’t be afraid of skinny jeans. Just because “skinny” is in the name, doesn’t limit their customers. Slim or skinny jeans on bigger guys can give you a smarter, more tailored look to your outfit by slimming your calves. The important area to focus on with the fit is the crotch and waist – you don’t want it too tight here fellas (it’s uncomfortable, as well as not looking great), and avoid anything that gives you too much of a “muffin top” – cover the waistband with a longer top or jumper if you need to.

At any given time, I’ll usually have a stock of jeans to pick from for different scenarios:

  • Blue Skinny Jeans
  • Black Skinny Jeans
  • Blue Ripped Skinny jeans
  • Black Ripped Skinny Jeans
  • Optional Seasonal Pair

Having a bunch of different styles lets you mix and match depending on the rest of your outfit, or the season – traditionally darker for the colder months, lighter for the warmer – but this isn’t a steadfast rule. Ripped/distressed for casual of course, and a seasonal pair could just be something I’ve seen outside of the norm that I like (last season, it was a red stripe down the side seam). Something to mix with shirts or t-shirts, shoes or trainers, smart or casual.

Another option with jeans is to look at premium brands. Levi’s is a prime example. Right, I know none of us particularly want to be spending £85 on a pair of jeans. that’s like, a video game and takeaway for a weekend’s enjoyment. Or a couple of indie games. Or 16GB more RAM. But hear me out: Levi’s have free length alterations, as well as in-store repairs and customisation services. Really, that lands you with a pair of jeans for a couple years. Investment pieces, right? Invest in yo’self.


Fashion isn’t always a top priority for most guys. Now, I’m not going to Fab-5 this up too much, but – when you look good, you feel good. You won’t believe me until you give it a try, so please – give it a try. Even if you just pop into a Topman with a friend and try some stuff on that’s outside your comfort zone. 

I was encouraged to write this article by a couple friends who – when coming out of recent break-ups or depressions – instead of taking them paintballing, I took them to the barber and clothes shopping. The result was their confidence bouncing back in a big way. Any guy who starts with some basic pieces, to build the confidence to then go on and maybe dabble in the more daring stuff, will notice a change in themselves and their confidence. 

So go, Winter has come, and you’re gonna look great through it. Warm too. You’ll be bloody warm in all this.




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