Fashion trends are constantly evolving. Each season, new fashions emerge highlighting trends that designers forecast will be the “it” designs of the year. Fashion weeks in major cities across the globe have been held for decades, celebrated, and anticipated events often thought to forecast the fashion climate. But many bizarre fashion trends from the past that were once stylish are now rather questionable.
Magazines full of stunning clothing inspiration from the past vary from decade to decade. Some fashion trends have staying power and manage to make a comeback every few years, but others have been beyond disappointing. There may be a particular fashion that people attempt to revive, but just because someone is wearing a certain style, doesn’t mean the trend in question is worthy of bringing back.
To gather this list of bizarre fashion trends from the past that were once stylish, 24/7 Tempo consulted several fashion-forward sources including Urban Matter, Society 19, Budget Fashionista, and Who What Where. (Perhaps ’80s fashion was your thing and you were a Gen-X Mallrat.)
This post was updated on October 25, 2025 to clarify hoop skirts were most popular in the mid-19th century (1860s-1870s) and provide an early 2000s history of the whale tail.
Corsets – 1900s
Corsets of the 1900s are not the same as corsets that fashionistas can purchase for themselves today. Modern corsets are made with soft material that gently cinches your waist without causing severe pain. Back in the day, corsets were extremely abrasive and harmful. They made it hard for women to breathe and crushed women’s ribcages.
Hoop skirt dresses – 1850s/1860s
During the mid-19th century, women wore hoop skirt dresses to keep the heavy fabrics off of their legs as a way of keeping their body temperatures down in hot climates. These days, a hoop skirt dress would be cumbersome and obnoxious to wear in public. Modern individuals would certainly raise their eyebrows at such a huge skirt style.
Boater hats – 1920s
In the 1920s, boater hats rose in popularity among both men and women. Men wore them for outdoor activities like playing cricket or going sailing. Not long after, women started wearing them to protect their faces from the sun.
Today, boater hats simply don’t have the same appeal. They don’t compare to modern hat styles that offer more coverage like sun hats and fedoras.
Heeled oxfords – 1930s
Heeled oxfords were popular in the 1930s, but they aren’t considered a fabulous or attractive footwear choice today. Back then, these shoes were meant to be worn in formal settings. They helped women show their peers how sophisticated and chic they were then. These days, heeled oxfords can be swapped out for simple close-toed pumps in a solid color.
Mini bowler hats – 1940s
Typically, people rely on hats to protect their eyes and face from harsh sunlight when outside. When mini bowler hats started rising in popularity during the 1940s, they didn’t serve a purpose. Their size didn’t allow for any coverage, rendering them sort of… useless. Now, people only think of wearing this hat style as part of a costume.
Bullet brassieres – 1950s
During the 1950s, bullet brassieres were considered super trendy among women. These days, most folks only think about bullet brassieres when they think of edgy musicians like Madonna or Katy Perry.
They’re known for wearing eccentric stage outfits during their over-the-top performances. Bullet brassieres make a woman’s chest look sharp and pointy. Modern bras offer a more rounded result.
Paisley patterns – 1960s
Paisley patterns were all the rage in the 1960s, but they weren’t able to maintain that level of love and admiration as time progressed. Head to toe paisley-patterned outfits would have style-crazed individuals using words like “tasteless” and “ugly”.
Bellbottoms – 1970s
Bellbottoms were considered trendy in the 1970s during the hippie movement and were often made of denim, cotton twill, or linen. These days, pants that have straight-legged bottoms or wide-legs are more common. If someone wore bellbottoms in public today, fashionistas would definitely raise their eyebrows in judgment.
Parachute pants – 1980s
Parachute pants are slightly similar to bellbottoms aside from one significant detail. They remain billowy from the hip to the ankle – all the way through. Bellbottoms are tighter over the thigh and looser below the knee, which makes parachute pants a tad more dramatic to look at. They were beloved during the 1980s, but not anymore.
Jeans under dresses – 2000s
Wearing jeans under dresses would be a total embarrassment today, but the look was beyond favorable in the early 2000s. Celebrities like Ashley Tisdale, Lindsey Lohan, Miley Cyrus, and Vanessa Hudgens showed up to red-carpet events wearing jeans under dresses frequently. These days, people are better off wearing jeans with a T-shirt.
Crocs – 2010s
The argument for Crocs is that they’re super comfortable to wear. The argument against them is that they’re horrendously unappealing to look at. Regardless of where your opinions fall on the matter, Crocs rose to fame throughout the 2010s following their 2002 release. If you choose to wear Crocs today, prepare to be judged by members of the younger generation.
Exposed thongs – 2020s
Originally popularized by pop culture celebrities like Britney Spears and Paris Hilton in the early 2000s, the trend of wearing exposed thongs surfaced again in 2020. Some outfits were designed with fake thong-like straps sewn onto skirts or pants. Other times, actual thongs were required to pull off this provocative look. The so-called “whale tail” was a hot topic just a few short years ago, but it’s no longer considered worthwhile.
The image featured at the top of this post is ©Photo by Scott Olson/Getty Images.