Where are all my Gen X readers? Raise your hands. I know, being the iconoclasts that we are, we’re not the types to make ourselves known. In fact, we’re often forgotten about. We’re a small, self-reliant generation that is perfectly happy to go overlooked. But we need to talk because the trends of our youth are back. It’s sort of weird seeing the things we once wore, that we now laugh at, being worn again by a generation who weren’t even alive when the looks were trendy the first time. I volunteer as a critic/mentor to fashion design students at The Fashion Institute of Technology, the school where I got my fashion design degree, and nothing is weirder than working with a student wearing almost exactly what I wore when I was in the same classroom over 20 years ago.

Yet it’s not just classrooms and kids who are not able to vote yet wearing the clothing from the ’90s anymore, we’re watching trends from this decade creep into all areas of fashion. It’s like watching a fast-moving train you can’t stop while knowing how badly it will end. And I realize that while I write this, somewhere a baby boomer will read this post thinking, “welcome to middle age, my friend.” We’re not the first generation who has watched clothes of their youth embraced by a younger generation who doesn’t remember them the first time.

Noted trend forecaster David Wolfe once said something about trends that I thought was incredibly wise. To paraphrase, he said that trends never come back full circle. Instead, they spiral and touchback on something that once was but is never the same. As someone who has lived long enough to see trends recycle, I agree. The 90’s span ten years and within those ten years, a lot happened in fashion. We had grunge, the waif look, techy Y2k trends in the late ’90s, psychedelic 70’s throwback in the early ’90s, tapered pleated pants as well as bell bottoms. I could go on. If you lived it, you know it. When trends reflect an era gone by, it’s never an exact replica.

Let’s also not ignore the fact that all of us who wore these trends the first time are considerably older and speaking of wise wisdom, my mom once said to me, if you wore a trend once you don’t wear it again. While wise, when the stores are flooded with trends from a time past, they can be hard to ignore. However, I think what my mom meant by her statement was you don’t wear trends you once wore the same again. I don’t have the same flat stomach I once did. There is no way I am wearing a top with a hint of midriff. Not only would I look ridiculous, nobody needs to see what has happened to my once firm abs. So today, I am going to share some tips for wearing the 90’s trend to work when you actually lived through the 90’s.


In these looks, I am creating outfits that address the 90’s trends in stores in a way that works for the age you are now to show you that it is possible to embrace what once was in a modern way.

Outfit #1

Blazers have become increasingly more relaxed, a total 90’s thing. When I was in high school in the early 90’s, I used to wear one of my dad’s old tweed sports jackets with a t-shirt, high-waist jeans, and booties. Sound familiar? We’re seeing this look all over again. Silk blouses are also back with a vengeance, something that was also popular back then. Silk charmeuse blouses are more of a late 90’s trend whereas the relaxed blazer was more early 90’s, but this is what happens when trends recycle, the timeline is rarely respected.

To give this work outfit a 90’s nod, I styled this double-breasted blazer from Vince with a balloon sleeve (balloon sleeves. Remember them?) silk charmeuse blouse from Club Monaco with high-waisted cigarette pants in olive and pumps by Via Spiga in a color called Thunder. Oh and remember block toes in shoes? Well, they’re baaack. Another trend that is back is large, minimalist jewelry, like this necklace from Kenneth Jay Lane.

Outfit #2

We know that pleated pants are a thing. They’re hard to ignore and the last time we saw pleated pants in earnest was in the 90’s. They petered out in the early 2000’s but by that time nobody cool was wearing them. But in the 90’s? For sure. I owned pleated acid-washed jeans and, yes, I loved them. I have to be honest, despite my fear of the flood of 90’s trend bringing back, like ridiculous shoulder pads, I am enjoying the idea that pleated pants will bring some comfort to my midsection after years of squeezing myself into skinny jeans like I was trying to jam toothpaste back in the tube. We’re also tucking our shirts in again. Who has tucked a shirt into their pants in at least 15 years? But with proportions changing, tucking creates this new shape.

I styled these black pleated pants from COS with a washable silk t-shirt from M.M. Lafleur and finished the look with leopard flats from Boden and chunky earrings from Madewell. And now with pleats and tucking back, say hello to belts. I styled this look with this one from ALLSAINTS.

Outfit #3

I started my career in 2002 when pants were incredibly low rise. I remember cleaning out closets and clients had these tops and sweaters that all were so short. What I realized was because pants had become so low rise, these tops and sweaters only appeared short however, back when these clients wore these old tops and sweaters, when pants were higher rise, they fit just fine. This is what is happening now. As the rises of pants are going up the length of tops are going down.

I styled these pleated denim style pants with a cropped sweater from L’Agence that I layered over a raw edge tank from Halogen in beige. I finished the outfit with square toe slingbacks and the same necklace in look #1.

Outfit #4

Slip dresses were incredibly popular in the 90’s and while I’d be hard-pressed to find any woman who remembers the 90’s that would want to wear one to work, slip skirts can be realistically worn. I will preface the recommendation of wearing these skirts with a disclaimer which I refer to as the fat in a Ziploc bag vs. the fat in a Tupperware container analogy. When you put fat in a Ziploc bag, it is left to jiggle around whereas when fat is put in a firm container, like a piece of Tupperware, it is forced to take that shape. The problem with bottoms without structure is the fat can jiggle around and will likely require shapewear. Think of your shapewear as the Tupperware container and a skirt like this will likely require some.

I styled this silk skirt from M.M. Lafleur with a silk button-down blouse from Equipment that I tucked and belted with this belt from Michael Kors. I finished the look with beige pumps and geometric wood earrings.

Outfit #5

When I see blazer dresses, I think of shows like L.A. Law and Ally McBeal, two shows that ran through the 90’s. Blazer dresses can be a real power move that harkens back to a time when women had to use things like power suits and shoulder pads that made them look like linebackers to show their strength.

I styled this blazer dress from Theory with the same slingback square toe pumps from look three and earrings from look two.

If the 90’s trends returning give you great pause, I hope these tips give you some help navigating them the second time around.