Keep Comfortable, Keep Warm & Stay Stylish

Dressing well can be a chore. In this horrible weather, and it is particularly horrible as I sit here writing this article, paying attention to what you’re wearing can seem utterly futile. In these situations, I think it is entirely acceptable to throw all your inhibitions out the window and simply blend in with the crowd; I know I do.

But even when our unpredictable weather does decide to remain predictable, even for a short while, I still find myself thinking: Do I really need to make an effort today? One of the biggest issues for me is that I don’t actually spend enough time out of my house (and out of work) to make it worth my while making a concerted effort.

I see no reason to dirty my ‘good’ clothes if I’m just going to take them off again when I get in the house (joggers are just more comfortable and I’m also notoriously spill happy). I can of course plan ahead, making sure I push the boat out if I’m out for a decent length of time, but for spontaneously at least, it all just seems so unnecessary. Putting on a blazer and shirt to nip to the shop just doesn’t seem worth the bother.

That’s why my style is undergoing something of a re-purposing. I’ve tried the fancy root; it’s all too much. I want throw on style; I want to get dressed in a matter of seconds, not minutes; I want to be comfortable in everything I own and wear; I want to be the person that always looks cool, comfortable and stylish, but never comes across as overdone.

It’s all about styling consistency. You might not be pushing boundaries, making the big statement or dividing opinion, but you’re always there, dressing well and looking good.

How To: Dress Down & Still Look Good

We sartorially inclined men can become too engrossed in our style; we can begin to ignore the world around us, we ignore the social trappings that make the world turn, that dictate the way we live, the way we work and the way we look. I’m all for people trying new things – being bold with their clothes, their colours or their outfits – it works, it really does. If I see a man walking down the street in a roll neck jumper, a double breasted blazer, tailored trousers and a pair of loafers, I’ll think to myself: damn he looks fine.

But I will also see the man walking behind him in a pair of jeans, shoes, a t-shirt and a cardigan, who has got everything right, his colours, textures, fit and shape and I’ll think, damn he looks fine too.

As fashion conscious men we should all be able to dress up and dress down. I know that I bang on about outfit appropriacy almost constantly but too often do I see men that have judged a situation all wrong. They have just gone too far, look out of place and out of character – the clothes might be great, but it’s still gone wrong.

But with all this (semi)ranting out of the way, I should probably clarify exactly what I mean by dressing down and looking good.

Lookbook Inspiration

Men's Dressing Down Lookbook Inspiration

Look 1

I’m going to keep pushing this kind of look because: One, I really like it; two, it’s so bloody easy; and three, it will work for everyone. It makes use of all those staple items that we men of fashion deem essential to own, it’s completely interchangeable and it takes no effort at all.

What makes this outfit so simple is that the base elements have their grounding in easy fashion and style. You can just throw it on and go, because there aren’t really any little details to worry about. Every man should own a pair of grown up trainers but they don’t have to be white, they don’t necessarily have to be low tops and they don’t always have to be Jack Purcells.

Sportswear trends are making trainers much more acceptable on the fashion scene, so think carefully about what you want them for, how you will be wearing them, and look after them with as much care and attention as you would your leather shoes.

In this look the chunky cardigan is essential. It’s arguably your statement piece, so having something a little different or a touch oversized could be just the thing you need.

The jeans can be switched out for chinos, cords or tailored trousers. Opt for bolder colours if you want to, or if you want something more relaxed think carefully about your choice of fabric – a pair of soft cords or flannel trousers might be just the thing for a lazy Sunday stroll.

To maintain the easy wear aesthetics, stick with something simple like a tee as your base layer, you could change it up with a shirt but once again think carefully about the look you’re trying to achieve. You don’t want anything too formal (although it could go that way), so opt for Oxford cloths, brushed cotton or flannels for a softer feel.

  • Asos Long Sleeve Crew Neck T-shirt With PocketAsos Long Sleeve Crew Neck T-shirt With Pocket
  • Slowear Zanone Chunky-knit Wool CardiganSlowear Zanone Chunky-knit Wool Cardigan
  • Reiss Pistole Wool Flannel Trousers GreyReiss Pistole Wool Flannel Trousers Grey
  • New Balance 565 Suede And Leather SneakersNew Balance 565 Suede And Leather Sneakers
Look 2

The transitional season can be tough to style. The temperature isn’t consistent enough to allow you plan so far ahead, so you could be freezing one minute and roasting the next – for times like these, a lightweight but sturdy jacket is the answer.

I’m a huge fan of the Varsity jacket and I think it’s far more versatile than people probably imagine. For lightweight jackets, it’s my preferred choice, along with my much abused Harrington. Opt for one in a muted palette and you have an outer layer that you could wear pretty much wherever you want, it looks great dressed up over a shirt or left simple and easy with just a white tee, jeans and some trainers/shoes.

Even if you go for a jacket that’s a little bolder, you still have a great deal of scope for use – just think carefully about what colours you might be putting together or stick to the basics that you know will always work.

Again, this is just a simple selection of clothes that you could throw on in a matter of seconds and know full well that you will be looking sharp all day. As with look 1, it’s totally interchangeable, so break out your leather or switch in some chinos and desert boots, it’s entirely up to you.

  • River Island T-shirtRiver Island T-shirt
  • Topman Black Knit Shawl Collar JacketTopman Black Knit Shawl Collar Jacket
  • Asos Slim JeansAsos Slim Jeans
  • Reiss Aster High Top Trainers BitterReiss Aster High Top Trainers Bitter
Look 3

This is one of my personal favourite winter looks. It’s easy to wear, easy to pull on in the morning when things are a bit dark and blurry, it’s fantastically warm and completely classic and timeless. Reach for a navy peacoat and you’ve got yourself the perfect winter look.

Now, I know I said earlier that simple style doesn’t really worry about making a statement, but I also know that many of you like making statements regardless of whether you’ve gone all out or just wanted to put something on. If you need something that will make you’re outfit stand out, coloured trousers are one of the easiest way to make an impact.

With a neutral coloured roll neck you can get away with pretty much any colour trouser you like, so go wild. My advice would be to keep the tones season appropriate but you are totally free to wear whatever you want.

Winter footwear however is another matter. As much as we all love our brogues, loafers and derbies, they just aren’t appropriate in winter, especially if they have leather soles. I wore my chukka boots out recently (I wasn’t anticipating the rain but I managed to keep them dryish) and was quite concerned by the fact that I had to make a conscious decision to walk on a roughed up surface and spent more time thinking about how fast I was walking and how much grip I had. Invest in pair of boots with a rubberised or vibram sole and save yourself some embarrassment later on.

  • Nn.07 Sea Wool Rollneck SweaterNn.07 Sea Wool Rollneck Sweater
  • Topman Dark Green Skinny ChinosTopman Dark Green Skinny Chinos
  • Reiss Moor Chunky Stripe Socks RedReiss Moor Chunky Stripe Socks Red
  • Asos Boots With Fabric Insert Side PanelsAsos Boots With Fabric Insert Side Panels
Recommended Pieces

With the above ethos and ideals in mind, here is a selection of current season items that you could invest in to dress down and dress well:

  • Topman Oat Textured Open CardiganTopman Oat Textured Open Cardigan
  • United Colors Of Benetton Shetland JumperUnited Colors Of Benetton Shetland Jumper
  • Allsaints Valley Funnel JumperAllsaints Valley Funnel Jumper
  • Oliver Spencer Bloomsbury Lambswool-blend Shawl-collar CardiganOliver Spencer Bloomsbury Lambswool-blend Shawl-collar Cardigan
  • Reiss Zackery Long Sleeve Denim Look Shirt BlueReiss Zackery Long Sleeve Denim Look Shirt Blue
  • Farah Vintage Albany Tobacco CordsFarah Vintage Albany Tobacco Cords
  • Farah Vintage Chino With Dropped CrotchFarah Vintage Chino With Dropped Crotch
  • Topman Grey Marl Crew T-shirtTopman Grey Marl Crew T-shirt
  • Saint James Navy Cream Meridien Long Sleeve Rib TopSaint James Navy Cream Meridien Long Sleeve Rib Top
  • Allsaints Stamp Cigarette JeansAllsaints Stamp Cigarette Jeans
  • Allsaints Hilliard ShirtAllsaints Hilliard Shirt
  • Topman Red Skinny ChinosTopman Red Skinny Chinos
  • Oliver Spencer Suede Chukka BootsOliver Spencer Suede Chukka Boots
  • Allsaints Buckley BootAllsaints Buckley Boot
  • Converse White Leather Jack Purcell PlimsollsConverse White Leather Jack Purcell Plimsolls
Final Word

Autumn/Winter is definitely my favourite season for style. I love the chunky knits, big boots, textures, colours and my winter coat. But it is also the most difficult. The same weather that draws out all the things I love also causes the problems we have to contend with everyday.

Dressing well is a central part of my life but I don’t want to have to struggle with it; clothes should be a joy to pull on and if it’s wet, windy and horrible outside, I just don’t want any hassle.

Styling consistency – and arguably perfect style – comes from being able to look good everyday of the week, not just on days that you pull out your best. This is why we NEED to be able to dress down and dress well.

As always, I want to hear what you guys think, so let me know in the comments below.

Will