Fashion Reboot: Casual Clothes: Step 2

Updated: Oct 23, 2020

Your casual wardrobe. Photo by Andrew Neel on Unsplash

Casual clothes are the heart of any man’s wardrobe. Whether you're 50 plus or not it’s these clothes that you are going to wear the most and it’s this look that will define you. So this is the place that we are going to start the fashion reboot. Set the right tone in the casual section of your wardrobe and it will make your image update much easier.

Relaxed does not mean sloppy

Now before we start looking at particular items of clothing let me make the following statement, casual and dishevelled are not the same thing. Clothes that are relaxed and comfortable do not have to be sloppy and rumpled. Whether we’re on a boys night (I know at 50plus that’s an oxymoron but you know what I mean) or at the match, or simply going shopping, looking good still feels great.

Photo by Andrea Piacquadio from Pexels

Creating a selection of casual clothes that make you look and feel good should not be that difficult. Celebrities seem to make it look easy! Now if you're anything like me you'll be saying I'm not a movie star, I don't have a stylist or a personal trainer, and I certainly don't have a million pounds in the bank. So how do I create a casual look that gives me my own easy cool look?

Photo by NordWood Themes on Unsplash

There are no fixed rules to looking good but there are some core items, which if you have in your wardrobe will go a long way towards establishing that effortlessly cool casual look that most stylish men over 50 tend to rock.

Clothes no matter what anybody says are not age-specific. That said to stay looking good as we get older our style does need to change. Most men in their fifties are not flattered by the clothing they wore in their twenties.

Key items in your casual wardrobe.


Whether you’re 50plus or not a pair of jeans is certainly a part of every man’s casual wardrobe in the 21st Century. I know some say that once you cross the big 5-0 you shouldn’t wear jeans and to those people, I say get real. Although jeans have been around for decades before we started wearing them, it was our generation (the 50 plus generation) who pioneered their movement from an item of work clothing, into a fashion statement and ultimately into a key element of everyday clothing. So if anybody has a right to wear them it's us!

Photo by Jan de Keijzer on Unsplash

Fit: Regular cut: Whether you're relying on jeans you already have in your wardrobe, or you've decided that for your fashion reboot you're going to buy a new pair make sure they fit. There are some men who can still get away with that fashion-forward look even at 50 plus and to those, I say good luck, but for most of us at 50plus no matter what we would like to think, that's simply not the case. For me, the key to looking good at 50plus is not trying too hard. So to ripped jeans, skinny fit, slim fit, hipster, tapered, bootleg I say no. As far as I am concerned for 50plus man it's the regular cut that looks best. This is the most forgiving cut when it comes to dealing with many of the issues (weight) that often dog men of our age.

Note to self, if you're carrying a few extra pounds don't buy jeans that belt up underneath your stomach, it just doesn't look good!

Fabric: medium weight. It will work in most situations.

Function: Relaxed, easy to wear.

Price: From about £35 to £100. You can go for the big-name brands but I've found M&S seem to do a pretty decent job. I know you're going to say who buys clothes at M&S but look before you dismiss them. For the man 50plus they offer a good combination price-quality and fit. Other companies that you might want to consider include Wrangler & Lee


Photo by Md Salman on Unsplash

Everyone has got t-shirts in their wardrobe. So the question here is do you have the right t-shirts to make you look good now. If you undertook step 1 of our 90 Day Fashion Challenge Wardrobe reboot then hopefully any t-shirts with holes in, or that are faded or simply worn out are gone. If you haven't well I know it was a great concert in 1982, but that was over 30 years ago! It's time to let that t-shirt go.

Try and ensure that you have at least 2 plain t-shirts in your wardrobe. One light ( white) one dark ( black or deep blue). Patterned t-shirts? Again there are no hard and fast rules but if there are going to be patterns or pictures then I suggest you keep them simple and keep them small. For me and I know it’s a personal thing at 50 plus it’s not fashioned first, it’s all about effortless cool.

Fit: Regular. It will look good and if it’s not too tight it will again forgive some of those issues that can crop up once you get past the big 5-0.

Fabric: Cotton/cotton mix – Cotton is a natural fibre, it breathes and is very comfortable to wear.

Function: A plain t-shirt whether worn on its own, or as part of a layered outfit works in most casual situation.

Price: Anything from £10-£50. M&S Supima Cotton t-shirt for £15

or Calvin Klein Underwear 2Pack for £20.

V- Neck / Crewneck jumper: Photo by Jonathan Zerger on Unsplash

Whether worn solo or layered over one of those t-shirts I just mentioned; or for a slightly smarter look layered on top of a button-down shirt, a good jumper is a key element in the 50plus man’s casual wardrobe. I'm talking about a relatively lightweight jumper here not chunky knit which certainly can have a place in anybody's winter wardrobe.

Fit: Regular. Tight jumpers even on guys who are in amazing shape always look like you trying just a little too hard, and for a man over 50, a figure-hugging top can reveal just a little too much. So again at least for your casual wardrobe, I am recommending a regular fit.

Fabric: Wool mix. This gives you the best of both worlds, the breathable qualities of a natural fibre with some of the maintenance benefits of manmade fibres ( easily washable, and hold their shape.

Function: The wool mix and relaxed fit or a regular cut make this style of jumper perfect for most casual occasions.

Price: Now these really cost pretty much anything from £19.50 at M&S for 100% cotton ( which is what I would probably buy ) to £65 for Lyle&Scott's designer Merino wool version.

Casual shirt:

Photo by Ben White on Unsplash

I know for some the words casual and shirt don’t go together and if you’re one of those people just go with this suggestion. It’s going to make a difference. A couple of the right casual shirts will give you choices that you haven’t had before and lift your casual wardrobe to a new level. Matched with a jumper as part of a layered look or just with a nice fitting pair of jeans a good casual shirt give your look that little bit of polish that makes you feel good whether you’re having a drink with your mates or wandering around the supermarket with your other half.

Fit: Relaxed: This is an item of clothing to chill in so no need for structure.

Fabric: Cotton or brushed cotton. – button-down if possible. Some people like patterned shirts. Checked would be the classic pattern on a casual shirt. I am not a pattern person, but it’s a question of taste and personal preference. Remember this is all about you feeling good about yourself.

Function: That brushed cotton look just knocked the edge off a shirt, taking it from smart/ formal and into casual/ relaxed.

Price: TM Lewin or M&S both off a good range at a keen price between £20 -£35.

Casual trainer/ shoe Photo by ANKIT on Unsplash

Big bulky trainers on a man 50plus who isn’t going to the gym for me is a No. I’m not saying that we can’t wear trainer type shoes I am just suggesting that we have to change the style. Bulky trainers out! The sleek casual trainer shoe is in. For me, their sleeker profile just looks right on a man 50plus.

Fit: Comfortable. No more squeezing your feet into shoes that don’t fit.

Fabric: For casual I would suggest some kind of canvas or perhaps a faux leather. You can go real leather but that will increase the cost.

Function: Comfortable footwear for evenings /days when you just want to relax.

Price: Around the £40.00 pretty much any sportswear/shoe shop.


Now, this really is up to you, but if your current casual coat is a bit knackered then change it. My personal rules keep it classic, keep it relaxed. Expect to spend anywhere between £100-£1000. You could spend what you want to get something that looks good and is going to last a while.

Photo by Andrea Piacquadiofrom Pexels

Author: JG

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