The Way Back: Fashion Trends & Lessons from the 90s

The 90s are back—fashionably speaking, anyway. While we still secretly covet the wardrobe of Cher in Clueless (don’t judge) we understand that decades of fashion influence should be just that—influence. No matter how much you love the look of any particular decade, incorporating that look into your wardrobe should always take the form of putting a throwback-style piece into the context of modern style, so as to avoid the inevitable questions about where the costume party is. But as students of style we know that from any decade, there are fashion lessons to be learned—and the 90s is chock full of them. Read and learn (and share your own 90s fashion lessons in the comments!).

90s Fashion Trends: The Lessons We Learned

Plaid is Forever

Plaid is Forever

When we think 90s fashion, we think plaid. In the early 90s era of grunge, however, it was your dad’s old oversized plaid flannel – color and cut didn’t really matter, it was more about the perfect blend of slouch and sloppy, to ensure that no one really thought you cared about what you were wearing since you couldn’t be distracted from your brooding long enough to worry about such trivial things. By the mid-90s, plaid had become the Britney Spears micro-schoolgirl-skirt, which for most of us normal folks (read: over 20) was better left to Halloween costumes (and even then, not so much).However, seeing as plaid hasn’t left us since then – either on the runway or on the department store racks—we credit the 90s with placing this classic pattern firmly in the spotlight, which we *heart* to this day. The lesson? Big sloppy is so passé—clean, structured, timeless cuts are what’s up.

The Update:

AE Sleeveless Plaid Button Down

AE Sleeveless Plaid Button Down, $19.99 from American Eagle

Pick one piece to showcase your plaid, and make sure it’s a piece that fits—an appropriate-length school-girl inspired skirt, a cute pair of tailored shorts, or even plaid tights or leggings, and keep everything else neutral and basic. And a plaid flannel for casual wear is fine, just make sure it fits, and leave the over-sized dad flannel to pops when he’s cleaning out the garage.

The Ubiquitous Chunky Shoe

The Ubiquitous Chunky Shoe

In the 90s, we all learned who Doc Martens was—well, WHAT Doc Martens were, anyway (fun fact: there is actually a Dr. Martens, which is the actual brand name—we googled it). Lug soles and fat toe beds became wardrobe 90s style staples

The Update:

On The Edge Cutout Booties

On The Edge Cutout Booties, $36.80 from Forever 21

Remember the rule—one piece from one particular decade of inspiration is enough. Wearing a chunky shoe with sleek cigarette pants and a button down denim shirt? Right. Wearing a chunky shoe with faded flare jeans and a kicky cropped sweater? Wrong—so very very wrong.

Putting Prints Into Proportion

Putting Prints Into Proportion

Prints were hot in 90s fashion circles—like, “a hot mess” hot. Restraint was not in the fashion vocabulary—think florals, stripes, zigzags, with a little neon thrown in just to make sure no one blended in to any possible background. We’re all about being seen, and mixing prints is fun, but walking around looking like the Fresh Prince of Bel Air? We’ll leave that in the past (but the theme song, of course, never goes out of style).

The Update:

Mixed Print Infinity Scarf

Mixed Print Infinity Scarf, $9.99 from Charlotte Russe

If you’re mixing prints, soft and subtle (and neutral tones) is key—small florals with small subtle stripes is pretty and edgy. If you’re not up to mixing, a fabulous print can be the focal point of your outfit – pick ONE printed piece, and offset with neutral classics. Think more edge, less clown.

The Dos and Don’ts of Denim

Justin Timberlake and Britney Spears

Denim will ALWAYS be classic, but in the 90s denim went weirdly astray with crazy washes, oversize overalls and patchy denim head to toe. Too much of a good thing is, well, too much. Need we say more?

The Update:

Merona Women's Denim Jacket

Merona® Women’s Denim Jacket, $29.99 from Target

Dark washes are always flattering, and since lighter faded washes are currently on-trend, we’re fine with them – as long as it is age appropriate, and you’re wearing ONE WASH AT A TIME. While we’re seeing denim jackets with denim jeans again (lord help us) we still think, for most of us, it’s safer to not go that route. However, a fab jean jacket with a pair of colored, great-fitting skinnies? Done.


For our latest article on 90s fashion head over to How to Wear the 90s Trend in the Dead of Winter.


Angela is a senior writer who's been hanging around TBF since way back in 2007. When she's not weighing in on the merits of, say, feathers as a fashion statement, Angela works as a bridal consultant in the St. Louis area. She also enjoys sunsets, and long walks in Target.