The Private Man

Attraction and dating information for all men

Middle Age Men, Fashion, And “Average” – A Rant

Guys, you dress terribly. Your clothes are outdated. Your clothes don’t fit. Your clothes tell the world that you simply don’t give a shit. You’re over 45, dress like you fucking care! I am embarrassed for you. The most damning insult I will give is this:

You look average.

Before my male readers get all defensive, do know that the beachside village where I live is not the zenith of fashion. I live in the culture of leisure and it shows in how the men dress ’round these parts. It’s pathetic. Even so, when I venture out and about into the working world (daily), I see way too much average and see almost nothing of masculine fashion style. It’s awful.

There is dearth of fashion resources for a middle age man to consult. Dressing “younger” is not the answer. Even that bastion of mature man ethos, Esquire magazine, is chock full of young guys wearing the hippest clothes. That’s fine for young guys. My readers aren’t those guys. Note: If my readers have good resources, chime in via the comments.

The poor fashion sense of middle age guys is indicative of a deeper and far more difficult problem. It’s an insidious emotional cancer based on a social expectation that finds masculinity something evil and to be suppressed. It’s this:

“Shut up and be average”

There’s that word again, “average”. A man should never be average. Average is the mortal enemy of confidence. Average is why most men live lives of quiet desperation. Average prevents men from approaching women. Average is fear and fear is not masculine. Average keeps men down. Women loathe average in a man. Yet if you simply look at how men dress, it’s apparent that men actually want to be average. I’m disgusted.

If a man wants to fulfill his relationship goals, average is the worst thing to be. Average is a corollary to “be nice, be yourself” and practically forces women to ignore him. Being ignored by women is the opposite of masculine charisma.

And about your hair. For that, you deserve an open-handed slap to the face.

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18 thoughts on “Middle Age Men, Fashion, And “Average” – A Rant

  1. Singleguyinnyc on said:

    Agreed. Try Pricy. . .but I’m wearing stuff now I never would have though I’d try otherwise. (I’m 42 and live in NYC.) I just hate shopping. Disclaimer: This stuff ain’t cheap, but it’s worth it for the longevity. Also? makes stuff that’s comfortable and wears really well BUT has a bit of a twist/edge/whatever to it. (I’ve no relationship with either company.) Oh. . one more thing. . check out “Dressing the Man” by Alan Flusser.

  2. I live in a militantly casual city, so whenever the weather permits, I throw on a sport coat. Even with jeans and a dress shirt, adding a sport coat sets me apart from the herd. It doesn’t take much to look good.

  3. Lamont Cranston on said:

    Oh, tell me about it. A couple of years back, I decided I needed to update my look. I grabbed those two venerable publications: Gentlemans’ Quarterly and Esquire to look for advice. What I saw were a mess of unshaven, smug, greasy-looking punks half my age with their hair in greasy clumpy messes, stubble, and their shirts untucked. I want to PUNCH those kids, not LOOK like them.

    So I don’t really know where to turn

  4. Great post Drew. As a help to those poorly-dressed men, I would recommend Permanent Style. In my opinion the best website there is for men on style, not fashion. Scroll through the links at the top to reach the earlier posts, which are the most helpful.

  5. I’m 48, rich, well read, in shape, I shave once a week on average, and regardless of what I wear, I get as much attention from the fairer sex as I can possibly handle.

    I buy 75% of my daily-wear from Bahamaville, Ralph Lauren, and Tommy Bahama.

    Want to be a player? It’s a choice and it’s a lifestyle, a journey – certainly not a destination.

  6. OK – there is such a thing as “classic” or “timeless” style. My preference is Brooks Brothers – they still have lots of the same styles for the last 70 years – of course they also have more “modern” styling – to each their own. Also, if you’re lucky enough to have one in your town – the Tommy Bahama store is outstanding – just stroll around there and start figuring out what you like – try on a few things, see what fits, etc.

    Here’s the trick – take a woman that you trust (not one that you are dating or “seeing”) this shopping trip if for you, not the woman, and if they are an SO and they see you buy something, they will think that life needs to be fair and want to buy as much (but of course, they will find things on pseudo- sale telling you they saved you money).

    1) take a woman you trust
    2) find clothes you like
    3) try them on – and let her see you in them
    4) ask for her honest and real opinion – let her know that this is because you want to up your style
    5) allow her to tell you and take it for what it’s worth
    6) then go to ebay or online outlets and buy the same stuff – size, color, etc.and save yourself some money

    OK, I’ve got one more tip…
    Shop the thrift stores – not to buy the crappy stuff, be very selective. Know what “labels” you’re looking for – and just run through the racks to find those one or two things. I look for three things (1) Lacoste (2) Ralph Lauren Polo and (3) Tommy Bahama – if I find those, then I start looking for stains, holes, the correct size, etc. – if it passes my filter, then I will buy it – if not, it goes back on the rack. I have about 5 Lacoste, 5 RLP, 3 TB shirts and sweaters – all about $3 each (or less). It’s a matter of going through 99% of their stuff to find the treasures.

    Bonus tip…
    Wear blazers and sport coats. And you can never go wrong with Navy wool blazer, white button shirt, jeans and boots. You will look better than 90% of the guys out there – and I mean all guys – regardless of age.

  7. I agree with Matt that a sport coat is an instant upgrade for jeans and a t-shirt. And unless you’re actively exercising, leave the sneakers at home and wear real shoes. This can get a little expensive if you want to have formal and casual shoes as you’ll need different pairs (not that you’re likely to get into women’s shoe-buying territory). I solve this by wearing western boots, which are, at least in NYC, distinctive and you only need a couple of pair; I have three, but am considering getting a pair of ostrich-skin boots.

    But, for God’s sake, make sure your clothes fit well. If you can afford it, cusom-made dress and casual shirts will make a huge difference. For other clothing, even if you buy off-the-rack, a good tailor is your friend. He can make alterations that make sure that your clothes are the best fit possible. That goes for suits, too; even if you’re buying at Macy’s or Men’s Warehouse, take it to your own tailor. Fully tailor-made suits are the best, if you can swing it. And no pleats. Pleats are for women.

    Now, go, and sin no more…

  8. Ghostbuster on said:

    It would have been helpful to see some photographs or drawings of what you find so objectionable. Instead of using young/old or trendy/out-of-date dichotomies, why not try to find a timeless style? The canonical references for gentlemens’ timeless style are these books:
    _Dressing the Man: Mastering the Art of Permanent Fashion_ by Alan Flusser (ISBN: 978-0060191443)
    _Gentleman: A Timeless Guide to Fashion_ by Bernhard Roetzel (ISBN: 978-3848002627)

    Since your blog is about dating, how about these articles?

    I found the forums at Ask Andy About Clothes to be helpful in discussing timeless style:

    The Sartorialist has photographs the include well-dressed middle-aged men that one could use for examples:

    Of course, I don’t have a closet full of bespoke suits and I’m typing this while wearing jeans and a t-shirt.

  9. Howdy,

    I’ve had good success with Men’s Wearhouse. I usually look for the lone female working there and have her help me with a couple of restrictions, i.e. no pleats and no khaki. Their ‘buy one, get one’ sales help a lot. Macy’s & Penney’s can have good stuff but you’ve got to sort through the dross and don’t expect any help.

    Next, get that stuff tailored. All my shirts have to be take in at the waist and it’s worth it. Women half my age ogle me in a shirt that feels almost too tight.

    Add a sport coat. That will make a pair of jeans, a golf shirt and cowboy boots stand way above the crowd. Oh, and your jeans should feel almost too tight. If they are baggy you look like crap.

    Do something with your hair. If, like me, it’s nearly gone on top; shave it and own it. Add some facial hair and you’ll look very masculine. Dye it if need be.

    Looking mature & successful is good, looking old & dull is not.
    Being memorable is good, blending in is not.

  10. Richard Cranium on said:

    This is a huge sore spot with 2 of the guys in my band. One is basically a bum this is his only outfit aside of his stage clothes:
    He literally wears this everyday. Might wash it once a month and yes he stinks.The hat covers the balding head that he won’t acknowledge how bad it looks and puts this smelly old man hair tonic on. The other guy is blind and is basically asexual so dressing “manly” ain’t happening. He still wears his high school band shirts and he’s 32. The other is in his 40’s we think (he won’t really say he might be older)

    Me? I dress nice. Designer jeans, boots, jewelry and a lot of shirts like this:

    I’m a musician full time so I have to be a little flashy. I had long hair for years but when it started going I went with the tight buzz cut. Facial hair depends on the mood right now I’m rocking a Fu Manchu in honor of Movember.

    Those two are honestly embarrassing to be around and despite having been told numerous times to clean up their act they just refuse to. But hey it’s less competition for us right?

  11. As Matt mentioned – wear a sport coat when can – or if a bit edgier – a black leather jacket.

    Shoes – DSW – excellent prices and a decent selection. Leave the tennies at home. Find a pair or two of “different looking” shoes – and wear with confidence. I have a pair of blue/gray suede shoes w/ blue laces I *love* – and women absolutely notice.

    Jeans – shop around. One brand I like for dress jeans are Mavi’s. Mid price range, great look.

    If you must wear a tshirt, make it a dress vneck – which looks great w/ a sport coat.

    Overcoat – black is nice, but camel hair rocks and gets noticed. Classy looking.

    Dress shirts – I get mine from Jos A Banks – their athletic fit button downs are pretty decent and the taper makes a world of difference – plus, they have long tails.

    Doesn’t take much to dress better than most guys – I’m an a midwest college town where ratty jeans and old tshirts are par for the course.

  12. John Dark on said:

    Women are attracted to stylish men. By dressing better than average you project a higher SMV. There is a book to be written on middle-aged men’s style (will let you know when it is done) but here are some basics:

    Women look at men’s chests. butts and shoes, so for dating, at a minimum:

    Wear good collared shirts with colour and/or texture. If you are older and your body is not what it was, a shirt with structure (Brooks Bros, Gant Premium, Italian top-end brands) will make you look in better shape. T-shirts on older men look embarrassing and women hate men who wear them on a date, it says that you don’t care about yourself (or the date).

    Trousers. Good chinos or casual wool are the answer. Fit and finish (stitching) is key here. Ralph Lauren owns this part of the market, you cannot go wrong. Kenneth Cole is good here and gives off a spirited, slightly sophisticated vibe. Do not get hung up about pleats. If you are short, heavy or just plain big round the middle, a single pleat pant will look better than flat-fronts straining around your abdomen. Do not wear Jeans! There are a million studies that show jeans on a middle-aged man are the biggest turn-off for women (especially on the first date). Always chinos for preference.

    Shoes. Critical. People still judge socio-economic status by looking at men’s shoes. To mix a casual look with good shoes, buy a pair of tan brogue Aldens which work well with casual. If you can get English brands look at Church (owned by Prada) or Cheaney. Cheaney are downright perfect style, especially for men with smaller feet.

    Have a stylish jacket. Going into good places in shirt-sleeves, screams Dork, that you do not know how to navigate the world with style. I like the Italian brands like Zegna, Canali. they go better with casual, especially good chinos. You only need one, it’s an investment.

    Good cologne. Buy Luca Turin’s book “Perfumes the A-Z guide” it is the definitive guide to perfume and lists the men’s best by type. If you want to do fragrance right (and safe) this book is a cheap investment before you buy fragrance. I cannot tell you how powerful a good fragrance can be on a date. The impact of fragrance on a woman is 10 times what it is on a man. I wear “Lonestar Memories” by Andy Tauer and it is the finest men’s fragrance bar none. Distilled essence of Clint Eastwood (in Coogan’s Bluff) at his sexiest. Women love it.

    Morale factor is important here. Dress well and you can look in the mirror and see how high your SMV is. Shit-testing. Good clothes on middle-aged men are so rare that women find it tempting to shit-test. You will always get shit-tested on good clothes. In my experience it is always by my date’s fat ugly friend who has not had a date since the dinosaurs roamed the earth.

    Style is your way of saying that you have played the game of life and won.

    Good Luck, Amigos!

  13. There really is no excuse for any man to dress poorly. The proliferation of mass customisation in the male fashion world means that anybody can get very good quality clothes, tailored to fit at reasonable prices. It is a choice to dress well…

  14. Tam the Bam on said:

    Fortunately I’m of an age where Dead Mens’ Clothes flood the thrift shops. If I can spot something decent before some frantic and sharp-elbowed eastern european Ebay magnate (who will get silly money for ’em), I get say a decent harris/donegal/herringbone tweed overcoat (basically as new, but decades old), or a pair of Grensons or Loake oxfords/semibrogues in brown or black, again hardly worn, never paid more that £15 quid for the coats and tweed jackets, up to £25 for the shoes. As a result, I have embarrassingly vast supplies, which will last me several lifetimes.
    This sort of thing.

    I was initially quite nonplussed by the frequency and quality of female Indications of interest that simply swapping out my (store-bought for work, and already fairly pricy and formal) Clarks and the like for the odd oxblood brogue, even fairly broken-in ones, had.
    Same goes for the coats. Thought I’d be channelling Worzel Gummidge, but seems to turn the heads and get sweet smiles from even college-age girls. Which is nice. (No, I am not a delusional old git, I know I’m just old enough to be their grandad, I set my sights more realistically). Lacks the disconcerting, slightly predatory glitter in the gaze of the decidedly post-Wall ladies closer to my own age.

    Took me a while to work it out.
    Seems there’s a deeply-embedded Brideshead/Edward Prince of Wales receptor in British women. So I got the haircut to match. Apart from carrying a Holland&Holland broken over my forearm, there’s not much more I could do. The one piece that does the trick is the B&W herringbone, very heavyweight. If summer ever breaks out again in my lifetime, I’ve got loads of mostly linen outfits, again very British and formal-ish, rather than some safari-suit abomination.

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