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Dressing for the Older Man

By: Hsin-Yi Cohen BSc, MA, MSt - Updated: 21 Oct 2012 | comments*Discuss
Older Man Dress Age-appropriate Age

While women are often bombarded with advice on how to age gracefully and dress their age, men often suffer from a lack of guidance. Thus, many men fall into two traps: either playing it too safe and therefore ending up looking stuffy and boring and much older than their years – or determinedly clinging to the clothes and hairstyles of their teens and early twenties, succeeding only in looking desperate and ridiculous. So is it possible for an older man to dress well without looking like he is trying too hard, look elegant and distinguished and yet still portray some of his personality?

Common Mistakes

A common phenomenon among men is selecting a look they like from a point in their life where they were feeling pleased with themselves and then trying to re-create and retain that look forever, never mind if that point in their lives was the early 20’s and they are now approaching their late 50’s! They essentially become stuck in an era and sadly, there are many examples to be seen of this every time you go out – even amongst celebrities. There are the men aiming to be clones of their teenage sons with their hoodies, garish T-shirts and rainbow Converse sneakers; still others clinging to their ‘surf bum’ days, dripping with loud graphics and flouro-colours or desperately trying to maintain “cool” via hip hop credentials. Unfortunately, while the underwear-visible-over-the-waistband, baggy-pants-about-to-drop-off look may just be acceptable in your teens, there is no way this will look attractive in middle-age, no matter how much aplomb you have! Similarly, long hair and/or ponytails really struggle as a style statement when your hairline has receded behind your ears or you only have 3 strands to cover the top of your head. Don’t even go there.

At the other extreme of the spectrum are men who feel that dressing extremely conservatively is the best way to look respectable as they get older but their desire to play it safe results in completely stuffy, bland dressing that conforms to all the stereotypes of “granddaddy fashion”

Sophistication and Style for the Older Man

Fashion and style does not have to only be for the young. There are many male icons who show that the approach of middle-age does not have to mean the end of stylish dressing and expression of personality – from Andy Garcia to Bruce Willis, to Kevin Costner, not to mention George Clooney, the man who has almost single-handedly made grey hair fashionable, and of course, Sean Connery, the epitome of the stylish, sophisticated older man who still rates high on many women’s “most sexiest” list despite being well into his 70’s.

So – for those who have no wish to pretend that they are still 25 but who don’t want to come across as a doddery old grandfather either, here are a few tips to keep in mind:

  • Take a good, honest look in the mirror and face reality. Be honest about what you have to work with – whether it is a receding hairline or an expanding waistline. Remember, many of the louder styles which you may have favoured in your youth will now draw more attention to sagging and excess fat which you may want. Ultimately, good style is about dressing for the shape you are in.
  • Don’t simply go by the year you were born. There are those who are prematurely middle-aged in their twenties! Keep an open, modern attitude and don’t be afraid to experiment. Just because you cannot wear the exact same things you wore in your early twenties does not mean that your choices are now limited to pastel polo shirts and khaki pants! Find different, more grown-up ways to express your personality and don’t be afraid to try looks which you never would have considered – they may suit the ‘more mature you’ far better than you realise!
  • Keep yourself in good shape – this will make dressing much easier and more of a pleasure. It will also enable you to possibly retain any more youthful looks you enjoyed for longer.
  • Keep up a good grooming regime. Style is more than just the clothes you wear but also your overall appearance, from your skin to your hair. So take pride in your appearance and take care of it. Looking unkempt may be cool in your teens – it just makes you look like a homeless beggar or a drunk when you’re middle-aged!
  • Learn from your fashion mistakes in the past. Don’t keep trying to flog a dead horse. In general, go for looser rather than tighter, especially if – like most people – you will have succumbed to a bit of middle-aged spread. The “tight-fit” look is often unbecoming enough on the young and slim – it is never becoming on the older and fatter!
  • Invest in better quality fabrics and cuts, even if it means you buys fewer piece each season. If you cannot afford designer men’s fashion, take inspiration from their stores and then look for similar styles in the high street. Generally, try to choose natural fabrics over synthetics.
  • Those living in warmer climates can afford to dress more casually, even as they age – for example, a man in his 60’s wearing a clean T-shirt and jeans is still acceptable, as long as the jeans are not spray-paint tight with giant logos or frayed cuffs.
  • Look for tailored, classic styles – even in casual wear. These will not date nor make you look like you are trying too hard to be “trendy”
  • Don’t forget accessories – you can make just as much statement with a stylish pair of glasses or a flattering hair cut, as you can with an overly-fashionable shirt. Shoes are worth investing in – if well taken care of, they will last a long time and very often, they will complete an outfit.
  • Layered looks are easy to achieve so look for stylish individual pieces of shirts, sweaters and sport jackets which complement your personality.
  • Jeans can be worn by older man – just remember not to go too tight or too baggy and anything with patches and rips is out! A pair of jeans with tailored, narrow legs paired with a leather jacket is a timeless look that can be sophisticated yet casual, youthful without being “too young”.

With a little bit of thought and planning, it is possible to dress in an age-appropriate way which still manages to convey style and sophistication and still express your personality.

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