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What Apparel Looks Bad on Men over 50?

Some apparel looks bad on any man. Some things look bad on some men, but not on others. What apparel, in your opinion, looks bad only on men over 50?
 
This is entirely dependent on setting, body type, and what you're going for. I wouldn't say there's a particular set, but maybe stuff that is decisively too hip/stylish. You look like you're trying to look "young" but it just kinda looks sad. I was at a party with someone's uncle who was dressed in what was "cool"...from like 2003. Light wash, boot cut jeans, untucked dress shirt with a big collar and the top 3 buttons unbuttoned, colorful sneakers, flashy watch. Dude was in his mid 60's, and it just looked...bad.
 
Forgetting about just plain bad taste (too subjective), anything that is not age appropriate. Not to say that one needs to dress like George Burns; just don't wear stuff that kids wear (and probably looks like crap on them), skin tight hipster outfits, etc.

Needless to say, if you are wearing a dress, make sure your shoes and bag match.
 
We have to assume this conversation excludes business attire. Even as business wear has become more casual certain standards are set in the workplace. For casual and semi-formal wear certain general rules should apply such as:

1. Don't try to dress like your grandchildren. Even if you knew who Justin Bieber was you don't want to dress like him.

2. Yep, the body is changing. Tight fitting anything generally will only highlight the changes. This doesn't mean you are condemned to a life of looking like a rumpled mess but rather that your tailor should be one of your best friends. It is OK (SWMBO approved) to have casual clothes tailored if it will make you look better.

3. Look for designer labels that are better fitted to your body shape. You are going to have to start trying clothes on before wearing them in public. Just grabbing a pair of jeans off the shelf that you have worn in past doesn't mean they will look OK now. Ain't no way I'm getting my 63 year old butt in a pair of 501's slims at this stage of my life.

4. Some of the classic styles look as good today as when you Dad and Grandfather worn them, I am especially glad to see Panama Hats making a come back for summer wear along with classic navy blazers and jeans in the evening.

5. If you are a supporting fan of the Jimmy Buffett Fan Club I can understand those shirts you are wearing (everyday?), otherwise flowers are for giving on special occasions and not for covering large portions of your body. At this stage I believe flowered prints or only OK as a accent piece.

6. Even if you are mister buff and at the gym 4 or 5 days a week neutral, warm colors are going to be the mainstay of your new wardrobe which you should continue to update as you get older. You worked hard to accumulate all the experience and leadership let some of it show in the clothes you wear.

7. Technology is not you enemy and can date you fast in public settings. Lose the flip phone and get a new smart phone. Fountain pens are stylish and say you don't comprise on certain values. Of course cursive writing is no longer taught in schools so no one will be able read anything you wrote in 30 years, but hey, you will be dead by then anyway with all the stress from staying in style.

Stay Loose
 
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Ill fitting clothes look bad on anyone. As long as your being reasonably fashionable, or wearing something timelessly styled, and/or dressing up or down to the occasion, you might not be the best dressed, but you probably wont be the worst.

Are you looking for things that you tend to see only on older gentlemen? for example, I see fanny packs, stonewashed jeans and bike (gym teacher shorts) on older gentlemen only.
 
My wife and I were talking about this yesterday. I saw a gentleman in his mid to late sixties in shorts. He did not look quite right in this get up let alone it was church.
 
You see a lot of fanny packs on older gentleman because it is where they are carrying their side arm. Of course if your going to wear shorts to church you should go ahead and buy a man bag (purse) and lose the fanny pack.
 
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Ill fitting clothes look bad on anyone. As long as your being reasonably fashionable, or wearing something timelessly styled, and/or dressing up or down to the occasion, you might not be the best dressed, but you probably wont be the worst.

+1 to this. It's good advice for whichever decade you are in.
 
For the gent approaching or entering into his 50s

1) Tailored, not fitted - all your clothes should be adjusted to your mature frame. Both work and casual clothes should (at minimum) be correct in length; the legs on your trousers / jeans / khakis and the sleeves of you jackets / blazers

2) No "cargo" anything (this is really an "over 30" item)

3) The bill of your hat always faces forward

4) "Novelty" tee shirts of any kind are prohibited

5) If you are belting your trousers above your navel, you have gone straight into your 80s
 
For the gent approaching or entering into his 50s

1) Tailored, not fitted - all your clothes should be adjusted to your mature frame. Both work and casual clothes should (at minimum) be correct in length; the legs on your trousers / jeans / khakis and the sleeves of you jackets / blazers

2) No "cargo" anything (this is really an "over 30" item)

3) The bill of your hat always faces forward

4) "Novelty" tee shirts of any kind are prohibited

5) If you are belting your trousers above your navel, you have gone straight into your 80s

I will always wear novelty tees. Then again, some 50 year olds look too old for that, some 50 year olds can pull it off if they are young at heart.

I have a pair of slacks from the 50's and the only way to wear them is above your navel...does that make me 80?
 

Doc4

Stumpy in cold weather
Staff member
People, like wine, are supposed to get better with age. You change and yet somehow remain sort of the same ... but different ... but still you. Remember being teenagers? All the social awkwardness, rigid conformity and yet reckless experimentation? That's what "the kids" dress like. When you get older, you start figuring things out. You lose the awkwardness, you stop trying to rigidly conform, and yet you no longer need to recklessly experiment ... because by now you pretty much know what works.
 
This is so subjective, but here gos:

Bracelets men wear opposite their watch arm. Yellow gold is the #1 offender.

2-3 days beard growth. You really have to be the right age and body type to carry this off properly.

No socks with a "business" suit.

Kiddish clothes on older men.

T. Gunn once said in an article I read. "Ask yourself, would Cary Grant wear this?"

My boss once told a group, who were strongly suspected of letting their wives pick their business attire. This was in the time of tangerine shirts, etc. " Gentlemen, we are dressing to please the business community, not the ladies."
 
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