Our Favorite “What Were We Thinking” Fashion Moments

image of Hobble Skirts

There are a million fashion trends we love this season, from tie-dye and destructed denim shorts to vintage band tees and oversized denim. But thinking about today’s trends got us reminiscing about some of the craziest and most embarrassing trends of the past. Luckily, the internet lets us all relive them together. Without further ado, here are some of our favorite “what were we thinking” fashion moments!

Hobble Skirts

The hobble skirt was a skirt or dress with a narrow hem at the bottom designed to significantly change the wearer’s stride. How did we get to this short-lived trend, you ask? In 1908, the Wright brothers took Mrs. Hart O. (Edith) Berg on a plane ride in France, making her the first woman to fly as a passenger. In an attempt to stay modest and avoid her skirt from flying up over her head, she tied it near her ankles. The rest, as they say, is history. And we’re glad this trend is history as well!

Breast Flatteners

Throughout the 1920s, boyish, almost tubular silhouettes were popular, and women did some interesting things to achieve the look, including wearing breast flatteners. By today’s standards and terminology, breast flatteners were just super-tight bandeau tops with straps designed to, well, flatten your chest.

Futuristic Fashion

During the 1960s, the United States and the Soviet Union were engaged in the Space Race, testing rockets to see who could get to the moon faster. Fashion was (apparently) inspired by current events, leading to the ”futuristic” fashion trend. We use the term futuristic lightly because we have yet to see these, um, styles appear as ready-to-wear. Maybe the designers were looking WAY into the future?

Safety Pin Face Jewelry

Honestly, it hurts to even think about it. In the 1970s, punk rock was alive and well, and safety pins shoved in your face just made sense to some people. We never want this trend to come back, nor do we recommend piercing yourself with items from your office. We fully believe you can be your most punk-rock self without stabbing your face with safety pins.


Now don’t get us wrong, we love a little butterfly accent, but in the ’90s, we went crazy with butterflies on all the things. Aside from the notorious butterfly hair clips, there were shirts shaped like butterflies, butterfly necklaces, butterfly handbags, butterfly earrings – you name it! Some of the credit probably goes to Mariah Carey, who dropped her album “Butterfly” in 1997. But that should not have given us the excuse to go so hard.

Velour Tracksuits

Matching velour tracksuits were popularized in the early 2000s by celebrities like Paris Hilton and Britney Spears. But you can thank your lucky stars if there is no photo evidence you ever wore a bright-orange tracksuit with Uggs, tinted shades, and a trucker hat. Again, what were we thinking? You can’t speak of this time without these bad boys popping in your head, so we suppose we could use the word ”iconic” to describe them. But don’t get it twisted; we never want to see them on-trend again.

Sources: Witness to Fashion / Smithsonian National Air and Space Museum / Harper’s Bazaar / Popsugar / CR Fashion Book

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