7 x tips on how to dress as a middle aged man……so you feel modern, without looking like you’re trying too hard
The majority of clients who come to me are in their 40s and 50s or older, as that’s the age you usually start asking questions about how to dress:
Am I too old to wear this - does it look like I’m trying too hard?
How do I look more modern and up to date without looking silly?
What can I wear to smarten up but not look too boring and classic?
I need to stop dressing like I’m still at uni, but I don’t want to look like my dad?
Everyone has their own style and there are no rules as such…..some people can carry off more “out there” pieces, and others look better in updated classics. So it’s a matter of finding out what your individual comfort zone is and then stepping out of it just a bit, so you don’t feel bored with your wardrobe and it grows with you and your changing lifestyle.
Sometimes when I chat to clients before they book in for personal shopping, they say “I don’t want a complete designer look” meaning they don’t want to look like they stepped off a catwalk in impractical and dressed up “try-hard” clothes, but they just want some tweaking and upgrading to their current wardrobe so it looks more polished and interesting.
I’m not going to lay out any do’s and don’ts, but here I’ve got together some tips on things to think about. That way, whatever your style is, you can hopefully translate them to how you dress.
And if you can’t, you can always contact me for help!
Left: Velasca Right: Wax London
Take a side step from your default choices
If you’re getting bored with how you dress and want to switch things up but don’t necessarily want to go for a whole new look, then take a side step from your default choices for a subtle elevation.
By that, I mean changing one thing at a time - you don’t have to go for a bright colour and an exaggerated shape or pattern, but you can go for just one aspect that’s different from your norm. You might have a classic check overshirt in your wardrobe already, but could you try out the same style in a more adventurous pattern like a jacquard (see above)? Or go for a different fabric - like cord or suede if you want to keep it simpler.
Or perhaps you usually go for blue jeans but could you try some ecru jeans instead? I’d go for a similar style to what you normally wear, as the change of colour will be enough so you don’t necessarily need a new shape or fabric as well.
If you feel self conscious about wearing something new and more fashion forward than you’d usually choose, then put it with your trusty basics that you feel comfortable wearing. Just make sure the silhouettes go together, as these do change over time (see point 3).
The trick is not to feel like an ageing hipster (as one recent customer put it!) or as if you’re trying too hard by going all out with a total look, but just changing one thing so you look more up to date and current.
I worked with a client last week, which provides a good example of why not to go for a total look He had some suede western style shirt jackets in his wardrobe - when we put them with denim, it ended up looked very “costumey”, so instead I styled them with some more classic grey flannel trousers and merino knitwear underneath - then they looked really stylish and modern, and the textures worked really well together
Left: Pinterest Middle left: Neem London Middle right: Universal Works Right: Grey Fox
2. Finish off your outfit with accessories
As life gets busier and there’s more things to take up your time, the details and accessories to go with your outfits can easily get forgotten about. I urge you not to though, as they make all the difference and can upgrade an outfit instantly!
Whether you’re going for a classic chestnut suede belt and loafers combined with a subtle pocket square to enhance a navy blazer and jeans, or some coloured, flecked socks and brighter trainers, to bring a navy overshirt and chinos to life, they really add personality to your outfit.
It helps to make an outfit look finished off and polished too, which is what you want as you get into your 40s and beyond…..it looks like you know what you’re doing with your image! If your style is quite classic you may just want to complete your outfit with accessories to look groomed and pulled together, or if you’re more adventurous you can use them to create a statement and set you apart from other guys.
Look at the image above for inspiration…..without the accessories that my friend David from Grey Fox blog has added to his outfit (on the far right), it might look quite classic, but by adding the pocket square and toning socks, it’s made his ensemble much more exciting.
Left: Pinterest. Middle: Alessandro Squarzi Right: The Sartorialist
3. Keep up to date with changing silhouettes
It takes quite a long time for menswear to change but every so often the whole silhouette shifts, and keeping up with that can make the difference between looking current or out of touch.
I remember when the narrower styles first came in and the shop assistants in Browns trying to get my (fairly classic) clients in very slim jeans, but they (and me!) just weren’t quite ready for it as it looked too extreme. Fast forward a year or so, and I recall seeing a guy on the street in straight jeans and thinking how dated he looked. The slimmer shapes had become the go-to style - even for middle aged guys.
Now, after years of skinny jeans and short bum freezer jackets, everything has gone the opposite way, and is much wider and oversized. I feel like I’m back at that stage again with the Browns shop assistants though - the wider shapes still feel like quite a statement and not mainstream yet, and not everyone is ready to jump on board. If that sounds like you, then stick with slim or slim straight which is the current classic (I know classics shouldn’t change but I think they do!) but be aware that things will keep going wider and anything too skinny will start looking very dated.
And if you’re up for embracing a looser silhouette, then you can give a nod to it with a slightly wider straight cut (see image in the middle) or go for it with a fuller wide leg. Alternatively, you could perhaps try out some trousers with a pleat front when you’ve been wearing flat fronted, to make a slight change to the silhouette.
You may prefer to widen the shape on your top half in which case you could go for a boxier style jacket……a smarter straight cut chore jacket can definitely be a good substitute for a blazer if your style is much more casual these days.
If you’re quite a short chap, be aware that a very wide look can make you look shorter, and possibly a bit “try hard” if you go extreme.
Also, when you change the shape of one part of your outfit, you need to balance it out with the other half in order to complement it. That was what I found during a recent Wardrobe Edit where we did lots of outfit building - some of the newer wider shapes didn’t go with the older slim and more fitted shapes so well. So we stuck to blazers that were a little boxier with wider legged trousers, and the more fitted jackets went with a slim shape on the bottom.
Left: Jason Jules Middle: Ami Right: YMC at Harvey Nichols
4. Explore colours
We all get to an age where we could do with a little help to lift our faces and looks! Colour can really do that for you…..when you’re wearing the right colour near your face, it can really help to smooth out shadows and wrinkles and bring attention to your eyes…..which is what we want, right?
It can also add a bit of fun to an otherwise plain outfit - an unexpected brushed pink Shetland sweater with a classic pair of beige chinos and chukka boots can lift your outfit (and quite possibly your spirits!) no end.
Black is a pretty harsh colour to wear for a lot of people….especially as you get older, so if that’s something you wear a lot of, consider switching to navy which is softer. It also goes better with other colours, whereas black can suck the life out of them and be a hard contrast. (Check out this blog post for more details on putting colours together.) You may also want to consider dark brown as a good alternative - very “now” albeit also rather 1970s!.
And remember, you don’t have to match your colours exactly - that can come across as a bit too try hard, but tone them ie: go for a lighter or darker shade of the same colour.
If you’re really not much of a fan of wearing colour, or have no idea how to put it together in your wardrobe….then either call me round to help, or just add some colour in your accessories - a surprise flash of coloured socks, or a bright scarf can really help to elevate your outfit and stop it from looking boring or “old-mannish”.
5. Make sure your clothes fit properly
So, this is important for everyone really, but becomes even more important as you get older. Your shape may have changed and it’s possible that you need to dress around your physique, instead of being able to throw on anything and it look good.
This is where alterations come in and make all the difference to your outfit eg: you may be carrying extra weight around your tummy and if you get the waist to fit on trousers, they look baggy on your bottom - so get the seam at the back taken in. Or you may need to go up a size in an overshirt so you can do it up comfortably but the sleeves are too long - again that’s an easy fix to have them shortened.
I think lots of guys expect to do alterations when buying a suit or smarter clothes but forget about it with more casual items. I used to work with another stylist who suggested that you put a portion of your clothing budget aside to use for alterations, and I think this is great advice!
A good way to start finding the right fit is by taking a couple of different sizes into the fitting room when you’re out shopping…..when I’m on a personal shopping trip for men, I regularly swap sizes for them to compare, and sometimes an item we weren’t sure about in one size, becomes our favourite when we’ve sized up or down.
When you’re in the fitting room, make sure you sit down when you have a shirt on to make sure the buttons don’t pop open over your tummy, and trousers are comfortable. And don’t just make do with the first thing you try on!
If you’re a shorter guy, this is even more important as it just doesn’t look good to have a polo shirt on that looks like a dress, or the cuffs of your blazer coming halfway down your hands. I’ve taken hundreds of shirts and polo shirts to the tailor to have them shortened.
If you need a tailor in London, I use Savva Tailors and would highly recommend them or Pinnas & Needles. Or if you have someone who can pin it and you don’t mind sending it away, I’d recommend the Clothes Doctor - they’ve done lots of things for me and I’ve always been happy with them.
Please don’t overlook this part, even if you have the most expensive clothes on, they’re never going to look polished and professional unless the fit is right, and as you get older this is even more important.
Left: Pinterest Middle: Private White VC Right: Pinterest
6. Go for high / low dressing in your outfits
When every item of your outfit is very formal it tends to look older, and perhaps a little fuddy duddy. Clients often say to me, that when they put on smarter clothes they feel like their dad, and don’t know how to smarten up without looking like that. And the opposite is true as well - if everything is casual it tends to look younger, and perhaps the sort of thing you would have worn at university.
So the solution is to go for a mix of formal and casual, to get a modern, stylish look that doesn’t look too “studied” but effortless…..and it’s also probably a lot more practical for most guys too!
It’s a bit of a balancing act and I’d say don’t go too extreme with what you mix eg: a very casual pair of faded, ripped jeans, with a very structured double breasted suit jacket is unlikely to work (unless you’re very skilled at styling). You’re better off going for things that are a little closer to each other on a scale of smart casual, such as dark jeans and an unstructured blazer which blend more easily together. Or if you want to wear trainers with tailored trousers, it’s easiest to do it if the trainers are a neutral coloured leather or suede in a minimal design, rather than sport trainers.
But try things out and have a play around - I had great fun doing this in client’s wardrobe recently, where we put a denim shirt with flannel trousers, a smart trench coat with jeans and trainers, and a cord chore jacket with a polo knit and tailored trousers. You could also try fine knit jumpers under blazers instead of shirts, or adding a tweed blazer worn as outerwear over a sweatshirt and jeans.
Another version of this is to upgrade your casual wear, so you level up the fabric of them whilst keeping the casual style eg: swap a cotton hoody for cashmere one, some cotton cargo pants for flannel ones, or a basic t-shirt for a knitted one. This gives that mix of high / low dressing that makes it modern and cool. As you get older, this way of dressing takes your outfits up a notch up without looking boring and staid.
7. Look at what other guys are doing
There’s a lot more options these days for seeing more mature guys who look like you in great outfits - look at Pinterest, Instagram, blogs like Permanent Style or pictures of celebrities in their everyday clothes for inspiration. Some websites also use older guys to model for them, so if you see a look you like take a screenshot or save it on Pinterest and start a collection.
You don’t need to be too literal in copying exactly what someone is wearing either but it’s useful to try and break down what it is about the look you like….. is it how they’ve put the colours together? The textures or patterns of the clothes? The shape of them? In the image above, you may like the check print but wouldn't wear the tonal look, baggier trousers or the hat…..you might wear it with some navy chinos and a darker sweater though…..or perhaps have the pattern in a long coat instead of a jacket and wear it with black and white……..it could be reversed to a light top, dark trousers if you preferred that.
Once you’ve figured this out then look at the clothes in your wardrobe to see if you have something similar. If their look feels too experimental for you and you’re not quite sure if it will look good, could you try out one element of it with your default jeans and a t-shirt (or equivalent default look) and see if it feels like “you”?
Ultimately it’s about finding out what your style is and taking aspects of more current looks that you like and integrating them with what you have. If you go all out with one look, it’s more likely to look a bit “fashion victim” but if you ignore current trends completely you risk looking outdated.
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Some people just have a natural ability to put stuff together. Sarah does!
You won’t be disappointed.”
Do you feel like you’ve lost your way with clothes?
You used to be pretty cool but life got busier, and now you don’t have time to focus on what you’re wearing so much.
So you go back to the same default items time and time again, but you’re bored and you’d like to switch things up a bit.
Trouble is, you don’t know where to start? How about a call with me to see how I can help?!
Better still…..if you’ve got a big birthday coming up, ask your loved one to buy you (or treat yourself) to a Total Style Upgrade.
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