[QUOTE=Dazzling White Diamonds]
I am currently wearing a button-down long-sleeved shirt that is tailored for a busty woman (which I am!) and a pair of snug fitting, slightly flared jeans. The shirt is untucked and the top and bottom buttons are undone. I’ve been told that it is an extremely flattering look for me (actually, I was told I looked damned HOT).
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Cite? Pics? 
[QUOTE=Slithy Tove]
What shoes, then?
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The rest: blue button-down shirt, slightly-faded but good-fitting jeans and a corderoy three-button sportcoat. I’ve dressed like this (extremely preppy) since I was a teenager - I consider it camouflage.
You can add me to the girls that find it damn sexy. And I don’t always need it tucked in, either. Both must be clean and neat though.
[QUOTE=Anaamika]
You can add me to the girls that find it damn sexy. And I don’t always need it tucked in, either. Both must be clean and neat though.
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I’m tucket. I’ve got one long-sleeved shirt that my SIL bought me that is cut specifically to wear untucked. And yes - nice an neat, fresh from the dry cleaners.
I feel better about this now. My shrew-like coworker can kiss my ass.
[QUOTE=Plynck]
Is it hard to find jeans with a button fly? At least the message is obvious, though.
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no no, the top two buttons of the shirt must be undone,lol
I hear button flys are a PITA, so I assume when a man is wearing a button fly he’s got just one thing in mind.
[QUOTE=OneCentStamp]
Casual Friday?
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It’s suppossed to be but damn if many of us aren’t pushing it from Monday on. I work hard and am over 40, which pretty much means if someone doesn’t like it I couldn’t give much less of a shit.
BTW, Winston, I also find button-down shirts and jeans to be sexy. Long-sleeved, short-sleeved, tucked or untucked - doesn’t matter. Shirt must be nice, clean and relatively wrinkle-free. Jeans must be clean, too!
Woo.
[QUOTE=lieu]
It’s suppossed to be but damn if many of us aren’t pushing it from Monday on. I work hard and am over 40, which pretty much means if someone doesn’t like it I couldn’t give much less of a shit.
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My practice is to dress casually monday through thursday, and dress “up” a little on fridays.
[QUOTE=Winston Smith]
Hmm? Seems ok to me, but who am I to judge?
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It depends on what circles you travel in. Preppy as a mass-market style came and went a long time ago. Do you have a house on Martha’s Vineyard? A trust fund? A son at Andover? Then by all means, continue to dress as you’ve always dressed … and your father dressed … and his father dressed. However, the rest of the world has moved on.
[QUOTE=Capa84]
When it’s warm enough outside to start wearing more club appropriate short sleeve shirts, then the fucky dress pants can come back out of the closet.
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Freudian slip of the week!
Dorky? How about nearly universal? Most of the men I know where this outfit pretty frequently, varying it occasionally with khaki pants. Heck, if I haven’t done laundry recently enough, I raid Himself’s shirt rack and wear that outfit myself.
[QUOTE=Pochacco]
It depends on what circles you travel in. Preppy as a mass-market style came and went a long time ago. Do you have a house on Martha’s Vineyard? A trust fund? A son at Andover? Then by all means, continue to dress as you’ve always dressed … and your father dressed … and his father dressed. However, the rest of the world has moved on.
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Well, I live in Marblehead, Massachusetts (which is like the Vineyard, but without the riff raff).
Well, are you wanting the “45 year old sailboat owner” look, or the “late 20s to early 30s pretty boy/metrosexual/urban” look?
Until my company was bought out recently, jeans and a button-down shirt was my 365 days a year wear. Which saved me some money - everyone else had to go buy khakis and shirts; I only had to buy khakis.
Dorky? Perhaps, I dunno. Do I care?
Definitely not my style. It makes me think of either Garth Brooks or Jerry Seinfeld, and I prefer to emulate neither.
Huh. That’s exactly what I’m wearing now.
I am a huge dork, for what it’s worth.
Glad to see from so many dopers that this isn’t dorky. I was gonna guess that it is indeed dorky - because of course I wear that look regularly.