Home > Style advice > How to Dress If You’re Over 40

How to Dress If You’re Over 40

March 30th, 2011

george clooney wearing a black suit

Ever wondered why older men seem to dress better while others seem to dress even worse than when were younger?

It’s a paradox, which has nothing to do with age and everything to do with each individual’s mindset and life choices.

When we’re young, we’re much more inclined to take care of our looks. After all, we’re energetic and in a permanent competition to attract the opposite sex.

But after a certain age, something amazing starts to happen. Some men become more and more comfortable, while the rest go into the opposite direction: they feel life passing them buy and, in an effort to look and feel their best, they start to learn everything there is to know about style.

If you’re in the first category and you’re looking to jump into the second one, you’ve come to the right place.

Style is for everyone, no matter how old you are. Its rules are timeless and, more importantly, they are easy to read and apply. So let’s help you find a style that suits your age while avoiding to look like a youngster or like someone who’s trying too hard.

Avoid fashion fads

Older men are often associated with certain qualities, such as wisdom, stability and class. Which is why the last thing you want to do when improving your style is to embrace fashion.

Forget funny t-shirts, forget what you see on the runways, even if some of the things you see there look like something you’d like to try. Start dressing a little more formal.

The absolute first thing you want to do is to start wearing shirts. Avoid t-shirts with logos or funny messages on them, such as this one:

funny t-shirt

Please, no matter how old you are, NEVER wear something like this! Take a look at the Very store to find some great clothes, not too flashy, at affordable prices – perfect for someone in his 40s.

If you’re already hooked on shirts, the next step is to make sure they fit you properly. A lot of older men wear over-sized shirts, most likely because this was cool when they were young.

Now I’m not advocating you should go for slim fit or, heaven’s forbid, skinny. Regular fit is fine for guys over 40. In fact, regular fit is cool for guys in their twenties as well.

I strongly suggest you take all your shirts and pants to the tailor and have him or her make adjustments to all of them. You’ll look a lot younger by wearing clothes that fit, and you don’t even have to make a new purchase!

Leave the past behind

Ok, I bet you’re probably a little confused. On one hand, I told you you shouldn’t wear all those baggy clothes that were trending when you were young, while, on the other, I told you that style is timeless, that it has old rules that still apply today.

Both of these pieces of advice are true. The thing is, you have to be able to distinguish between what looks good in terms of style and what doesn’t.

I already told you that baggy clothes are a no-no and that all your clothes should have a regular fit.

But that’s just the tip of the iceberg. You have to know each and every clothing item that is considered timeless and cool, at any age. So here’s a small list to get started:

– sport coats

men style ebook

- chino pants
– classic leather jackets
– v-neck and roundneck tops
cardigans
– overcoats
– and, of course, the omnipresent shirts

You can assemble an entire wardrobe with just these items and, if you make sure they all have the right fit, you’re already ahead 90% of all men your age.

Don’t be afraid to accessorize

Older doesn’t have to mean boring. Watches, scarves, sunglasses, pocket squares, ties, hats, caps and so on – these are all excellent for when you’re 40, 50 and beyond. SO go ahead, stop being afraid of what others might think and try a few of them on.

old dior aviators

photo:besportier.com

Don’t wear your work clothes outside of work

If you’re used to wearing a suit every day for work, you have to learn to relax your outfits when you’re NOT doing your job. Try something a little more casual, such as chinos, jeans, leather jackets. This isn’t something specific to men over 40, it’s something every man out there has to keep into account.

business casual outfits

photo:http://4smart.net

Instead of wearing your best office suit to dinner, why not couple a blazer with a pair of modern, straight leg jeans, a simple dress shirt, and a pair of casual boat shoes?

brown leather boat shoes

Blazers and sport jackets also work fine (I’ve also written an article about those two – please read it).

Keep it simple

Don’t try to be very flashy. Leave the loud patterns and flashy ties to the young generations.

For instance, wear simple designer jeans instead of rugged ones.

Notice how the pair of black jeans below fits the person perfectly. Notice especially the bottom of the jean and how it “follows” the legs.

diesel jeans

Tip: try to shave often… a beard will make you look older.

Style advice



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  1. April 7th, 2011 at 17:22 | #1

    I think older men should stick to classic looks, think suits, leather accessories, a good briefcase and a good pair of shoes. As you mention – the simpler the better! I don’t think men need to necessarily keep up to date with fashion, rather invest in key pieces that are timeless.

  2. July 17th, 2011 at 02:34 | #2

    Indeed Hannah. And to quote Bernhard Roetzel, an international authority on men’s style:

    I find that I stand out in most crowds by trying not to stand out and dressing in the most conservative way possible.

    (He gave us this nugget in the exclusive interview I took him for BeStylish.)

    This doesn’t mean we don’t have to educate ourselves as men, though… there’s a lot to be learned… just that, sometimes, more is less.

  3. Joe
    January 8th, 2012 at 06:10 | #3

    Question, I’m a guy in late 30’s. I have a hard time trying to figure out what I can wear on weekends for a casual look. Now I like straight-leg jeans and a fitted contemporary style un-tucked shirt, but nothing fancy. Solid colors or no pocket plaid shirts like from the rail at Nordstrom. But I don’t want to look like the old guy trying to look 20. What do you guys think. Should I get rid of my fitted contemporary shirts for Kohl’s regular fit polos? Or am I good.

  4. Kevin
    April 11th, 2012 at 09:50 | #4

    Boat shoes? Come on.

    Your young age shows here. They scream “dork who is out of touch” not “classic” (unless you’re on a boat).

  5. April 11th, 2012 at 10:20 | #5

    Kevin,

    Just check out photos from Pitti Uomo, the most appreciated clothing festival targeted at me. You’ll see a lot of Italians (and not only) wearing them.

    I agree that they signal youth – right on about that. But consider the rest of the outfit. You can make them work as long as the rest of the outfit isn’t flashy. They can be that thing that tells the world “I’m still in touch with what’s going on.”. As a person over 40 you don’t have to dress classy all the time. A casual situations is just that: casual.

    Boat shoes have long been “off the boat”.

  6. Mark
    September 8th, 2012 at 22:23 | #6

    You say older guys shouldn’t try to look younger, but then you say don’t grown facial hair because it makes you look older. Sorry, but I don’t agree. If anything, I think older guys SHOULD have facial hair. Clean-shaven faces can make a guy look less masculine.

  7. September 8th, 2012 at 22:54 | #7

    I’m saying you should look like you’re TOO young. Looking 20 years younger is a sign that you’re trying too hard to reover all those years where you didn’t know about style, women and so on (or did know but couldn’t get them).

    Ideally you’d want to look your age. Maybe 2-3 years younger or 2-3 years older if you want.

    Clean facial hair can be a sign or masculinity or a sign that you’re messy. You can look messy but you have to know how to do it, meaning that trim your facial hair and make it look right.

  8. Sabrina
    October 9th, 2012 at 13:57 | #8

    My other half was 40 at the weekend and although he looks younger than what he is he’s suddenly become very aware of his age and hates the thought of dressing too young but has met a wall as he really doesn’t know what styles suit him. During the week he have to wear jumper, shirt and trousers to work which is fine but at the weekends with the children he’s worried he looks like an old dude trying to be young. Suit jackets with jeans etc are great for evening but what casual do you wear during the day shopping or out with the kids etc? he likes converse and straight leg jeans but what tops? and other trouser options? Remember he’s 40 so fashion is a lot more over the top now than when he was younger and although I like things such as chinos and boat shoes it’s hard for him to convert to this new metrosexual society where mens fashion are more excepting and forgiving.

  9. December 6th, 2012 at 12:14 | #9

    That is a meaningful line – Leave the past behind. If you are keen to observe, that is very true. Most men are still dressed in the trendy outfits which made them look cool when they were in their teens or early 20’s. As you add more years to your age, your fashion taste has to mature too.

  10. Mark
    January 19th, 2013 at 16:54 | #10

    I’m 44 and I still wear hi tops chucks. Is that ok? Of course I wear them with a straight cut pair of jeans and a polo shirt. For me, chucks is timeless. And yup, I guess it doesn’t matter if you’re 45 or 65 years old, as long as you don’t wear super loud neon colored shirts and trousers, you won’t look like you’re trying hard to look like your 20 year old son.

  11. January 19th, 2013 at 18:18 | #11

    Hey Mark,

    Thanks for the insights!

    Agreed, you shouldn’t try to look like a 20 year old… but how about looking like a 30-year old?

    I think 30 is the perfect age to try to come back to (so to speak) with style once you’re over 40.

  12. Tanya
    February 1st, 2013 at 13:06 | #12

    Boat shoes = wanker. Simple.

  13. robert Anderson
    February 18th, 2013 at 00:13 | #13

    George, I don’t agree with the comment about the facial hair and men over 40. It is an individual thing and not across the board. Some men over 40 look much better with some facial hair that without. It needs to be trimmed and neat and maybe colored or at least some color added bit it can cover up a multitude of “sins”…sings of aging of done right. I hate a thin gray or gray mix beard and I do think it make a older man look older , but trim it up and add some color to it and it can work. God bless you.

  14. February 18th, 2013 at 00:28 | #14

    Robert,

    I completely agree and I appreciate your comment. Removing facial hair will generally make you look younger but each of us is unique so some rules may not apply to some of us.

    Glad to hear you found a way that works for you to look younger!

  15. February 22nd, 2013 at 16:14 | #15

    I think the key term that is not emphasized at all in this article is “sophisticated”. I’m not 40 and I’m not 20, but I can spot a sophisticated man 100 yards away. However, it must be noted that a 21 year old man has a much different perspective on style than the 40+ year old. 21 thinks 40+ is old, and 40+ sees 21 as kids. I agree with much of what was written about avoiding childish trends, and mixing work attire with social appearances. Men turning the page to the 40+ chapter have the opportunity to have their wisdom taken seriously for the first time in their lives. However they aren’t old men so throw away the boat shoes… unless you just stepped off your very own boat. So, hey, dress the part, and avoid kids’ trends bc no one will take you seriously. Consider the slim fit look for a moment, this isn’t a trend when applied to a men’s suit. A properly tailored suit will always have a slimming look for which the man it was made. Thank your tailor, every time. No one wants to look fat. This brings me to a commonly overlooked aspect of dressing your age. BUY CLOTHES THAT FIT. This is true of any aged man, but more important for the 40+. Society kinda lets it slide when a young man wears a baggy or tight suit. We just assume that he’s still hasn’t made it yet, and he’s still figuring out life. To the 40+ man: Prove to the world you are sophisticated, don’t dress like the kids, and wear clothes that fit. You can pick any style from there. I could easily say more, but I already rambled.

  16. Maton
    April 10th, 2013 at 22:13 | #16

    Do not listen to this people who think they know what is trendy, what is trendy anyways….monkey see monkey do, like the kids who are now wearing these baseball caps with a straight flat bill, back in my days the kids who wore the hats flat had a mental problem, be happy and be yourself. “Life is too short”

  17. D
    April 22nd, 2013 at 01:25 | #17

    Fashion is like shit. It comes out hot but it usually stinks. I dress for me and no one else. I know of no one that I need to impress more than myself. Dress how you want.What ever makes you feel good.

  18. April 22nd, 2013 at 08:16 | #18

    You guys need to start reading every article form the beginning, you clearly have no idea what this site is about. This is a STYLE website not one about FASHION. Huge difference.

  19. John
    May 24th, 2013 at 06:41 | #19

    Nobody is going to tell me what I should and shouldn’t wear. Is this what kind of society we have become, where we are dictated by demographics? I’m over 40 and my mates are around the same age and we all wear reasonably fashionable clothing – modern jeans, printed t-shirts and sneakers. I work out and tend to wear tight-ish t-shirts to show off the results, I’m not flabby yet! If you don’t like it I don’t give a toss.

  20. May 24th, 2013 at 10:38 | #20

    John,

    A society where you listen to no one and you have to reinvent the wheel every time is pure chaos. Your outfits with jeans and printed t-shrits are so generic they’re not even worth mentioning. So why bother coming to a style website if you’re not interested in dressing better?

    My advice works whether you like it or not and if the only reason you’re not applying it is because you can’t hanld the fact that someone is “telling you what to do”, tough luck bro.

  21. Ted
    July 24th, 2013 at 17:39 | #21

    I’m 63 and have always liked to keep up with the latest fashion trends, but I am cautious about buying clothing that won’t make me look as though I’m trying to look younger. I’m just trying to look good. Luckily, I have a 21 year old daughter and a 26 year old son whom I take shopping with me as they have good fashion sense as to what works or not for dad. They keep me looking good and contemporary without looking stupid.

  22. GAC
    July 30th, 2013 at 18:40 | #22

    I’m 42 and dress in t-shirt and jeans; shorts if it is hot outside.
    Cutting the lawn, fixing my truck, walking the dog, grocery shopping are all a reall part of one afternoon. I work as a technician in a lab and use a labcoat all day. There is no way I’m changing clothes four times a day to look like I have some sort of fashion style.

    Suck it up and don’t judge a book by it’s cover.
    An arse-hole can dress nice and still be an arse… And a nice guy is still a nice guy regardless of what he is has on.

  23. msknowitall
    November 14th, 2013 at 21:06 | #23

    I think old people have earned the right to wear whatever the f* they want to, and just because some 12-year-old needs to feel unique and hip (while wearing the exact same thing their peers are wearing because everybody knows 12-year-olds are pathetic lemmings) doesn’t mean gramps or granny shouldn’t rock a pair of funky aviators if they want to. Trust me when I say no older person really WANTS to be 20 again but they still want to look good in whatever fashion they decide defines that. Besides, they typically have more money to spend on cool sh* anyway, they earned it, and why the f* not. So, in conclusion, STFU whippersnapper.

  24. Hardey Leone
    December 22nd, 2013 at 02:33 | #24

    One should wear what makes them happy. It is your own style that people should see. If you don’t have ‘style’ that is also ok!

  25. Tcass
    February 8th, 2014 at 08:37 | #25

    I’m astonished at the number of people who are getting defensive, and preaching that they are going to stay “original” with their style (or lack of). The author is trying to give style tips, if you don’t agree with changing your look to a more appealing one, then why did you come to a style website? I don’t agree with being completely clean shaven either, I think facial hair is a masculine thing as long as it appears tended to, but I can’t attack this guy for trying to be helpful.

  26. Liz
    July 14th, 2014 at 03:08 | #26

    Come on people. This is for advice. Of course you can take it or leave it. Guys who “don’t give a F_ about style shouldn’t be typing in a search for “what men should wear in their 40’s.” I’m just trying to help my husband feel better about his style, since he asked me. We live in a rural area, yet visit Chicago every so often. If he wants to feel good about himself WHEREVER he goes, be it a greasy spoon, or a high end urban restaurant- well that’s why we’re here. We’re not going to get our personal aggressions out on someone who’s job is to help give a bit of insight to those who are ASKING for it.

  27. Peter
    November 18th, 2014 at 22:38 | #27

    I’m 47 and feel like I have lost some of my swagger. This article is just what I needed. Advice. As I have never been really into fashion, I find that I actually have no style. I can dress nice sometimes but the staples that you mention, I have none of.You gave me something to think about and I thank you for that. Keep doing it! You have been a big help to me.

  28. Hardey Leone
    November 19th, 2014 at 01:13 | #28

    Wow….talk about an ego. Who do you think you are? This is really
    quite a basic post. Nothing to brag about. @George

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