There was the recent incident of the checked shorts. They were hideous. They looked like swimming trunks but they had to be worn in the hours of daylight to go to the pub. Not surprisingly, they went inexplicably missing next time there was a laundry run. They’re the kind of things you look at someone wearing and say “jeez, what were you thinking?”
Have you tried colored tighties? Both of my bros grew up wearing white or light blue tighties and now wear colored ones (Middlebro, colorful prints; Lilbro, black or grey). SiL tried toget Middlebro to wear boxers and he says it feels like he’s got swimming trunks under his trousers… “you oughta wear swimming trunks or trousers, but not both at the same time!”, says he.
Okay, avoiding those might be a good idea, they’re pretty bad. But you can have my Jesus shoes when you pry them from my cold, dead feet.
Please allow me to mention my pet clothing peeve.
Nothing ruins a fine landscape quite like draping it in shapeless fabric.
The spouse usually dresses fine in a geeky sort of way–jeans, polos, t-shirts with silly sayings on them, athletic shoes, that kind of thing. He looks fine most of the time, and he’s one of those kinds of guys who always looks neat and put-together even when wearing grungy clothes (as opposed to me, who almost always looks vaguely rumpled even on the rare occasions when I wear “nice” clothes). The one clothing-related thing I can’t manage to convince him of, though, is that you don’t have to tuck everything in!
Really. You don’t. He says it looks “unkempt” if you don’t tuck it in. He tucks in everything–T-shirts (which is fine), polos (ditto), sweaters (ugh), hockey jerseys (double ugh! At least I managed to convince him that you don’t tuck in your jersey when you’re actually *playing * hockey, 'cuz it makes you look silly). When he lounges around on the couch watching TV in shorts and a T-shirt, he tucks the T-shirt in. He tucks in his shirt when he’s sleeping!
It drives me a little batty, but aside from teasing him about it, I don’t say anything unless it’s particularly egregious (like the sweater thing. Fortunately he doesn’t like sweaters so he rarely wears them). I figure I’m not enough of a fashion maven to be casting too many stones, though both of us acknowledge that I’ve got better men’s-fashion sense than he does (which is weird, since I’m female and have nearly no women’s-fashion sense).
Yikes. Okay, now I’m the bad one. Granny panties and men’s plaid flannel pajamas are what I wear to bed in winter and granny panties and boxer shorts and huge t-shirts are what I wear in the summer. Granny panties are my fave. Very comfortable. Hey, nobody ever said *I * was sexy. Seriously. But my boyfriend’s PLEATED PANTS are still worse, I swear.
Exactly the reason I wear long sleeves year round.
That’s so smokin’ hot it’s just…wrong! If we were both single I’d be compelled to jump in muh truck head that-a-way, on the chance that, after exercising due diligence, perhaps I’d get to view this amazing get-up.
Now, to address the dilemma in your OP, it’s handled thusly at my place:
The lady of the house buys all clothes. She is also in charge of getting rid of all clothes.
There are two hanger bars in my closet. I’m allowed to select from the bottom rack to go about my day-to-day meanderings.
If we’re going out together or I’ve got some muckety-muck deal to attend, she selects from the top rack and places her selection on the bed. I put it on. End of story, no problems! 
To explain a bit, that was kinda’ the deal when we first got together. I told her I could cook, clean house, do laundry, repair plumbing and pay bills, but clothes were a mystery to me. She took it from there and ran with it.
Now, covering it up is one thing, but smothering it in two layers of knickers is just going too far.
[sub]I really hope you meant that as an either/or rather than both.[/sub]
John Carter of Mars, you are an awesome dude! That delights me so bigtime that you find my flannel pjs-granny pants combo hot. That is just *way * cute! It really isn’t, trust me! Wow, you have a truck. Way cool. I like trucks and bourbon and Jimmy Buffett. Too bad you’re married.
Anyhow, good for your wife. That sounds like a great system. I wish my boyfriend would go for something like that, the top closet rack and bottom rack thing. He still thinks he knows what he should wear when it comes to fancy-pants dressing stuff. It’s not so. He needs to listen to me, but it’s a struggle, let me tell you! We need to have that kind of arrangement with the clothing. It would save a lot of clothes cringeing situations.
Umm, yes, well…me too! Other factors not withstanding, if I ever get back to the Inner Harbor we’re gonna hang out, right? I’ll buy the drinks and you’ll sing karaoke. We’ll be rockin’ from one end of Fell’s Point to the other.
Last time I was there it was a blue moon. If I get there only on a blue moon it may be a while. Still, the water taxi was nice, with the full moon and all. Maybe one day…
John Carter of Mars: You’d have fun, no doubt! I hope, anyhow. You romantic dude, you. Yes, come hang out! Seriously! You and your wife. We’ll show you a good time. We can all go to the Admiral’s Cup in Fell’s Point and do melon ball shooters and stuff. Then go to John Stevens and eat mussels. Yum. Email me and I’ll hook y’all up. Room here to stay (small apartment but we can squeeze ya in) or we can get you a cheap hotel room. Also, water taxis are okay but sailboats are way better.
Oh yeah, in the spirit of the thread I actually started…
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Pleated big pants: bad.
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Sneakers with socks: bad.
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Sandals (mandals) with socks: worse.
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Boat shoes with no socks: good.
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Sneakers/track shoes with all outfits: very bad.
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Comb-overs: bad but somehow touching.
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Favorite ratty t-shirts: annoying but charming in the right place and time.
In the immortal words of Burt Bacharach:
*Don’t make me over
Now that I’d do anything for you
Don’t make me over
Now that you know how I adore you
Don’t pick on the things I say, the things I do
Just love me with all my faults, that way that I love you
I’m begging you
Don’t make me over
Now that I can’t make it without you
Don’t make me over
I wouldn’t change one thing about you….*
I am red-green color-blind and when I was 13 (back in the era of Nehru jackets) I had heard about this thing called “color-coordinating” your clothes, so I thought I would try my hand at it. I put on what I believe were wine-red bell-bottoms, a tee-shirt that I think was dark pink, socks that may have been brick-red, and an orange, fringed belt. I was proud of this ensemble until I passed my mother in the kitchen on my way out the door. “Young man, where are you going?” she asked. “Out,” said I. She replied: “Not dressed like that, you’re not.” It took me years to figure out that wearing (what were to me) different shades of the same color is not color-coordination.
If my mother had thrown out these clothes, I would have accepted her judgment. But if a significant other did so, I would be looking for their replacement. I don’t like it when anyone makes my decisions for me. Having said that, this does not seem to be a problem for you and your boyfriend, so no criticism is intended. Just wanted to add my two cents.
I can’t tell you people how disappointed I am in you, letting this get to 93 posts without someone taking a dirty shot at it.
My husband is mostly very well put together, clotheswise, but he does have one pair of pants that are spectacularly unflattering on him - they’re old, they’re somewhat ratty, they’re pleated, and they’re too short. He puts them on, stuffs his four inch thick wallet in the back pocket, and all of a sudden, my good-looking baby looks kinda funny. Oh well. It’s just pants. I didn’t marry his pants. Oh, and there’s the red sweatpants that he wears with the bright yellow sweatshirt sometimes. I’m pretty sure he does that just to bug me, though.
(He tucks everything in, too. I think some guys find comfort in being tucked in all the time.)