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

Girl taking selfie with retro camera, wearing plaid

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. This way, you sidestep 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, but make sure it fits.

Two girls wearing plaid

When we think 90s fashion, we think plaid. In the early 90s era of grunge, 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. The goal was to ensure that no one really thought you cared about what you were wearing. After all, 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. That little bit of fashion for anyone over 20 was better left to Halloween costumes (yeah, not even that’s OK actually).

Even so, 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.

Today’s Plaid

Button down plaid top
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. Try 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.

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.

Wear that chunky shoe, but don’t mix decades.

pair of doc martens

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. We wore them with our oversized plaid shirts, to be as unapproachable as possible.

Today’s Chunky Shoe

Chunky sandal with cutout
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.

Mix your prints, but with restraint.

Woman wearing multiple clashing prints

Prints were hot in 90s fashion circles — like, “a hot mess” hot. Restraint was not in the fashion vocabulary back then. 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).

Today’s Mixed Print

Two printed scarves
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. But pick ONE printed piece, and offset with neutral classics. Think more edge, less clown.

Double up on denim. Just don’t cross this line.

Justin Timberlake and Britney Spears wearing all denim.
I bet JT and Britney wish no one ever captured this look.

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?

Today’s Denim

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. You can mix washes, but only in a very conservative kind of way. See our post on how to do it here.

Need more 90s fashion inspiration? See How to Wear the 90s Trend in the Dead of Winter.