I  struggled to find an outfit for the letter U, since its usage seems  predominantly limited to the less pleasant words in life—words like  ugly, unkempt, unclean, and underwear. Also unfashionable. I  call myself the "Unfashionista," so it stands to reason that at least  some of my clothes would be less than trendy. As long as you  look good in it or it makes a statement, I'm always in favor of  wearing something a little outdated or just plain odd.
But have I ever assembled a whole outfit out of the outdated and odd? Well, as a matter of fact, I did just last week, for my "Quirky"  outfit. While that ensemble was calculated to include my most  outlandish clothes and accessories in the goofiest combination possible  (while still trying to look semi-sane for my employers), today's will be  focused on clothing that was once stylish but has gone out of favor, or  has never really been in favor at all!
I  started with the shoes. These shoes have extra-long pointy toes that  are certainly not trendy now, but were for a brief period during a time  when I wasn't paying attention to fashion. More on the intricacies of  toe lengths in my footnote (get it?) below!* They also have kitten  heels, which are always a topic of hot contention  among the fashion set. Oddly enough, while these shoes would have been  solidly "unfashionable" a year and a half ago, the tides are currently  turning in their favor, with more and more kitten heels and longer toes  making an appearance.
The pants,  on the other hand, are no one's definition of stylish, and might never  have been. They are a short-legged, slightly flared (boot cut), grey  corduroy. They're also by Faded Glory, a bargain brand of dubious  distinction. My former housemate abandoned them in 2012, and they've  been, since then, what I wear when I want to be comfortable and warm,  but never when I want to make a great impression! Their stumpy legs  aren't a great pairing with the elongated shoes, and neither is brown +  grey a particularly popular color combo, but in this case it  was perfect, because the next unfashionable item on my list was my  cardigan/duster/sweater coat that just happens to be brownish-grey!
This  style of ruffly sweater seemed to enjoy a lot of popularity right in  the middle of my organic market days (I had a coworker who wore one  pretty much constantly), but presently it's all about clean lines,  oversized silhouettes, and a slightly masculine vibe. That doesn't stop  me; I wanted a knee-length cardigan, so I just bought this sweater  (used) a few weeks ago!
Under the  outmoded sweater is a plain brown camisole. I don't think basics like  this will ever go out of style; the only reason I chose this particular  garment is that I needed something to tie in with the brown shoes.
Next,  jewelry. I have heard through the grapevine that the statement necklace  is dead—and you only have to look through a few pictures of stylish  people to realize this is true; anyone worth their fashion salt has  already moved on to delicate metal pieces and chokers. But, oh, those  heady years of huge colorful plastic-and-metal necklaces will live on  forever in my memory...and, let's not kid ourselves, in my day-to-day  style. I'm going to wear my statement necklaces from now until eternity!  But now, at least, I'm ready to admit that they are unfashionable.  Especially when their curiously bright colors clash so strongly with the  muted tones of the clothes around them. 
Related note: this fashion  challenge has had me wearing a whole lot more plain old browns, blacks,  beiges, and greys than I would like, but I guess it's natural to  gravitate to neutrals when you have to continually create cohesive themed outfits  out of all the unrelated separates you have in your closet.
So  there you have it. A 4-piece outfit assembled exclusively from the  embarrassingly out-of-date. It pained me a little to step out entirely  clad in history's rejects, but, I did it (paradoxically) for fashion!
* Ready for a digression? Here you go: As I have recently mentioned, I have never been into shoes with long toes. Even when I was a kid, I had a strong aversion to women's pointy-toed shoes. That might have been a bit of my mom's influence, since I think she also opposed them, though perhaps that was more for comfort reasons than stylistic ones. My own opinion on pointy toes was that they just added inches to the end of your foot, making it look long and ridiculous (more recently I discovered that pointy toes can be very artfully designed to end just past your real toes, and I don't have the same distaste for these more subtly pointed toes—in fact, I now even recommend them for when you want to look sophisticated). Since I already had a bit of an insecurity about the huge size of my feet (which, at an 8.5 - 9, are actually perfectly average, even downright dainty relative to my height, which is slightly above average—but insecurities do not listen to reason), the last thing I wanted to do was wear shoes which made them look even bigger. So when pointy toes gave way in the late 90's to monstrous clodhoppers, I was an enthusiastic adopter! The overall proportions of a huge platform completely disguised the length of my foot, making me feel like I had small feet. In fact, I loved chunky shoes so much that I wore them well into the era when they were no longer stylish. Apparently in the early-to-mid-2000's, really long pointy toes were once again at the height of fashion (I judge this based exclusively on promo shots for the 2004 Mean Girls movie), but I totally missed that! Fortunately, I still got my chance (whether I wanted it or not) to rock the saber-toe look when a friend's sister gave me a pair of hers from what I assume was that era. I was about to re-donate the long-toed foot-pinchers when it occurred to me that they might be the subject of a very interesting craft project. So I kept them around, and all of a sudden, they were the perfect shoe for my U-day! End of digression.

 
 
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