Wicked Wednesday — I Shouldn’t Have Worn That Outfit

While getting our photo albums out two weeks ago to look for our worst hairdos we noticed we’d made some questionable fashion choices over the years too. Wickeds were you a trendsetter or fashion follower? Is there a fashion period you wish would come back? And which fashion trends do you hope never darken the doors of the fashion world again?

Liz: Stirrup pants! Anyone remember those? I have no pictures, thankfully, but those were definitely a horrible trend that should never make a comeback. I’ve seen reminders here and there over the years that are threatening to return, but thankfully they’ve never gained traction.

Jessie: Shorts of all kinds! I’m barely 5’3″ and I need absolutely no help in making my legs look any shorter. The only shorts I own are the stretchy sort and I wear them, reluctantly, on my home treadmill. My entire summer wardrobe is made up of dresses which are cooler, more comfortable and look great too.

Edith: I must say, Liz, that I felt very chic in my pink stretch stirrup pants tucked into white go-go boots, with a pink windbreaker over a white sleeveless mock turtleneck shirt. I was in ninth grade, had just outgrown my baby fat, and I thought I looked quite stunning. But who didn’t look stunning at that brief stage between awkward end-of-childhood and… well, never mind. I guess the oversized square plastic glasses frames of the early 80s, and the huge shoulder pads get my vote for questionable fashion. I was not, however, too nonconformist not to wear both myself!

awfuloutfitSherry: When I was in my teens and twenties I was pretty confident of my fashion choices. However, this picture of my thirties points out how horribly wrong I can be. The worse part about the picture is my daughter posted if on Facebook and it keeps getting bumped up to the top when someone new sees it and leaves a comment. I cropped Bob out but really green shorts with a black and red sweater — what was I thinking?

Julie: I’ve been watching Perry Mason movies from the eighties. That was a train wreck of a fashion decade, and I loved EVERY minute of it! Bring back the shoulder pads! Tunics over leggings (real leggings that you can’t see through)–everyone looks good. Button earrings–I’ve still got them. My worse fashion choices are when I look dowdy. Dressing in your 50’s is a fight between being age appropriate and being comfortable. Honestly, the 80’s fashions would help with both!


Readers: Your questionable fashion choices? Or ones that seemed borderline but later were trend forward? (And isn’t it even trend forward to use that phrase?)

26 Thoughts

  1. I think I spent a lot of my earlier life trying to look invisible, or to dress like my grandmother. Villager, John Meyer of Norwich–anybody remember those? (I think Talbot’s is the current equivalent.) Classic, conservative–boring! I didn’t even own a pair of jeans until after my freshman year in college. Oddly enough, my daughter tends to dress the same way, only now it’s considered retro.

    1. Life without jeans? Oh, my. I sewed trim down the side to spiff mine up. When I worked in the financial industry I did love the whole classic suit/silk blouse outfits.

  2. Funny, ladies! I have photos of myself as Moby Kate, 8 months pregnant with my now 30 year old son. I had on a blue and cream maternity dress, vertical stripes (I had gained 60 lbs) and the permed hair!!! What was up a bubble cut perm with ear flaps?

    1. Oh, Kate. Wish I could find my pregnancy pictures. I was Edith as House, having gained 55 lbs (and I’m only 5’1″…). For some reason I thought it looked good to wear red homemade overalls that were a little too short, with slip-on Birkenstocks because my feet had swollen. Not my best look!

  3. Let’s put it this way–last year when I needed to look a bit less casual than usual for Malice, I had to enlist one of my blog buddies to take me clothes shopping. I have no fashion sense. Thank goodness I can wear sweats to work in!

  4. In the early 80’s I had this black pleather baseball style jacket. I thought I was the epitome of coolness. Lol! I cringe now to think of it.

  5. Fashion? What’s that? I go into a store and buy what they have and wear it until I am forced to go clothes shopping again.

  6. Mini skirts and platform shoes. ARRRRGHHHH!
    And yet, even today, I see girls wearing them. I want to grab them and warn them, but no, they have to learn for themselves.

  7. Stirrup pants–dear god, I thought that was just some horrible fashion nightmare, but I guess they were real. Sherry, I love that photo. You look happy!

    I agree with Julie that dressing in your 50s is a challenge. I am not a fashion plate, but I fear looking dowdy. And I’m short. I wear lots of skirts and thank goodness for the popularity of leggings. I also don’t wear jeans because I don’t find them comfortable. From time to time, I challenge myself to go a week without wearing black pants. So far, I don’t think I’ve made it past day 5…..

    1. Ramona, I think I have five pairs of black pants in my closet. Or maybe six. The rest are gray. At least the jackets are a little more interesting. But I don’t think I own a skirt any more (unless you count the Stevie Nicks homage skirts from India).

    1. I had some dresses that were so short they came with little matching short/bikini bottom things. I can picture one dress perfectly — I loved that dress.

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