Mamaduck – Do you live in California? That sounds like the uniform of most teenage boys here (with Vans substituting for Converses).
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I think your wife is taking the wrong approach. I notice that ever since I told my husband he looked really hot in a new pair of black skinny jeans (and proved it), he's bought several more pairs. And he wears them a lot.
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There ya go! If your wife just said, “honey, if you wear these jeans I promise you won’t have them on long.” 
“A seersucker suit is appropriate in any former Confederate state which voted for Goldwater in 1964 from Easter to Labor day.”
Ha! My H does have a seersucker suit, but I think the last time he wore it was to a boat party in the 1980’s with a bow tie. It got passed down to my son, who I don’t think has had an occasion to wear it. It looks a little too dandy up here in the North, IMO.
But S did indicate that he needed some new sweaters, and H said - why don’t you just raid my closet when you come up here, which S agreed to do. I of course did some recon to make sure this was a good move, and I have to say, classic sweaters make this a reasonable move. S doesn’t really have personal style, though, so therefore preppy is as good as anything.
White sneakers are like ponchos or “granny-chic” grey hair. They are only cool if you are obviously young enough to have missed the trend the first time around. Macklemore can wear white velcro sneaks ironically. Most 55 year old guys cannot.
@nottelling we’re in ROVA (rest of Virginia - not DC area).
@Scipio - They haven’t “suddenly” become a crime. 
Something understated like the old school Stan Smiths can be OK but bigass New Balance are only cool if you were cool before you put them on.
@nottelling : “New Balance, weirdly, are among the most stylish of the white sneaker trend.”
@saintfan : “bigass New Balance are only cool if you were cool before you put them on.”
Ok, now I am having sneaker confusion.
Am I hip and trendy, or not? :-??
“wear white velcro sneaks ironically” What does this even mean?
Watch a few Macklemore videos… In one of his videos, he rocks an old fur coat that looks like it was made of dead rats’ skins.
I do not know where nottelling got the idea that NB is among the stylish… If it is from the link posted by someone up thread, well, the info is outdated. February 2014 might as well be 364 BC.
This thread has made me laugh (some very witty people here on CC!), cringe (uh oh, does my husband dress like that??) and made me think about his attire. While I spend a fair amount of time contemplating MY attire, I spend much less on his, even though he does look to me somewhat to provide for him (happy to do so; I’m a shopper and he’s not). So, having said that, I hope more will post, including pictures of what men in their 50s “should” be wearing. And, yes, I know that there really is no “should” as everyone can wear what they want. However, for those of us who have an interest in staying current, it’s nice to be advised.
I showed D1 (24) the photos of a couple of the nicer/upscale sneakers posted upthread and her belief was that those were too young for her dad. I just spent more than I ever have on a pair of Allen Edmunds shoes for dh and he really likes them and D1 approved so I’m on the right track, possibly. Dh has definitely moved away from the baggier jeans, white sneakers and pleated pants but, particularly away from work, wears jeans with a polo-style shirt tucked in with a belt. Apparently a no no! Who knew?! I’ve tried to get dh to wear a darker wash but he prefers a medium to medium/lighter wash. Otherwise, he hasn’t been all that opinionated. So, please, for those who “know”: share more about what a fashionable man in his 50s wears!
Nordstrom does feature New Blanace in their shoe line up but I’m convinced by general observation that they keep them in the back and only break them out for the right demographic. At my gym men over 75 wear gray or navy New Balance “running” shoes. Men over 60 sometimes branch out into white New Balance “tennis” shoes. Everyone else wears Brooks, Asics and Nike. The “cool” old guys wear Pearl Izumi.
The truth of the matter is it doesn’t matter. I have traveled in a lot of places, I visit my D1 in NYC all of the time. We eat out all of the time, at some fine restaurants, and regularly visit museums, etc.
I have never felt uncomfortable in NYC, Spain, Seattle or my small town in New York with what I am wearing.
I want to look stylish. I like it when others, especially women, look me over. But this tucked in or not, one jean vs another, one brand vs another all seem completely irrelevant in most of the country. And maybe even many other countries.
So OB, wear what you want or wear what your wife wants, to keep harmony and enjoy some extracurricular activities!
For casual wear I really am not fond of “high fashion” for men. For men in their 50’s I am drawn to that outdoorsy Orvis look. I don’t really get involved with what H buys in the way of clothes, but he does purchase a lot from Orvis and he looks good. Kind of a “country gentleman” look.
Wow - New Balance shoes are considered very trendy here. Young guys wear them with jeans; you can make custom combinations online and I see them around town.
^^^Within each brand there are multiple styles. New Balance makes good running shoes as well as some casual shoes. Those are not the ones we are taking about here. I’m sure most people ordering those custom styles would not be caught dead in the gramps’ clogs aka NB walkers.
" only cool if you were cool before you put them on." Yup.
My experience with cool people is pretty much limited to the LA, NYC, and Bay Area contemporary art scene. I see a lot of young, cool people wearing New Balance sneakers like this as street fashion:
http://www.barneys.com/New-Balance-998-Sneakers-504023471.html
I’m not cool at all and don’t wear sneakers as street fashion. I’m just reporting on what I’ve seen.
And, I agree that an unfashionable middle-aged guy does not look fashionable in white clod-hopper sneakers. My original point was just to counter the cry that sneakers have been out of style for 20 years when every fashion magazine for the last couple of years – including in the last six months – has had a feature on sneakers AND they seem to be worn by the folks whose main goal in life is to be seen as cool (ie certain folks hanging around every gallery opening).
Lately my husband has been looking very, very nice. I don’t recognize him.
When I ask where he got the jacket he’s wearing, or the great looking shirt, or can-I-touch-sports coat he looks at me like a pea pod hatched from under the bed and asks, “Don’t you remember? You bought it!”
He has had this stuff tucked away so long, walking around looking like 1987’s Bruce Springsteen that I had just decided to stop looking at him. Suddenly I’m thinking his inner Sean Connery is trying to come out.
Nottelling, those shoes in your link do not even remotely resemble the NB that have been discussed here. Compare the shoes you linked to these:
http://m.llbean.com/product.html?skCatId=68368&bc=#68368
Agreed! The only reason I even know that the some of the cool kids were wearing New Balance sneakers is that I had to ask someone what the “N’s” on everyone’s shoes stood for. I assumed it was some sort of political statement. And, anyway, as I said upthread, the trend seems to be fading.
H works in a very young industry (video games) so he works very hard to walk the line between age-appropriate and “cool”. There are many items of clothing that are just too young (very skinny jeans, turned up cuffs on jeans, vests, sneakers, etc). He thinks that he’s cultivated an “old guy hip” look. I don’t know about that, but he usually looks fine in public - ie. my kids and I are not embarassed. Now, let’s talk about his facial hair, which is his pride and joy. He got rid of his beard when the hipsters started going full “Victorian street preacher” and now sports a full, bushy Sam Elliott style stache. He does get compliments on it, as well as several gay pick-up attempts (S says it makes him look like a “bear”). I tolerate it and pray that his next look is a little more conservative.