The Decades That Dressed Us
A Modern Wardrobe Inspired By Forty Years of Fashion
For me, television is best consumed admiring the wardrobe and styling departments’ hard work rather than a script, character development, or even the plot. Besides, no one is really watching Emily in Paris to tune in for her latest flavor of the week, are they?! Whether she ends up with Gabriel, Alfie, or Marcello is beside the point. We're here for the clothes, people. The clothes.
Recently, my latest binge has been a complete rewatch of Mad Men. I had “watched” the series before, but never in its entirety. I missed entire seasons, character arcs, and pivotal moments. Whoops. Yet, somehow, I still confidently told friends that I had watched the series. And while I’d love to report some personal growth and say I paid more attention to Don Draper’s pitches or Roger Sterling’s one-liners, I still found myself dissecting every hemline, silhouette, and accessory as if I had an assortment review the next morning.
Watching seven seasons unfold over the course of a decade left me thinking about how misleading our memories of fashion can be. We have a habit of remembering decades by their loudest trends.
Reducing a decade to one defining look made me think about how I want to remember the decades I’ve lived through. Let’s go back forty years. Not to relive iconic trends, but to rediscover how each decade defined great style.
1986
At the start of the decade, Lisa Birnbach published The Official Preppy Handbook. Originally intended as a satirical guide to the preppy lifestyle, it became an unexpected cultural phenomenon. By the mid-80s, many of the book’s style cues had become part of mainstream American fashion. Brands like Ralph Lauren, L.L. Bean, Brooks Brothers, and later J.Crew helped cement prep as one of the defining aesthetics of the decade.
Yes, I was two years old in 1986, but prep will always be my first love language. And if you’re anything like me, August arrives, and I want to trade a tank top for an Oxford shirt, even if the weather completely disagrees. Fall will always belong to prep.
1996
If there was one television character everyone wanted to emulate in the mid-90s, it was Rachel Green. Her wardrobe of slip skirts, babydoll tees, high-rise denim, loafers, and tailored separates was just as influential as her haircut.
Off-screen, Carolyn Bessette embodied a different kind of elegance. Her clothes felt edited, intentional, and unfussy. On September 21, 1996, she married John F. Kennedy Jr. in a private ceremony on Cumberland Island, Georgia. Narciso Rodriguez’s understated slip dress became one of the most memorable wedding dresses of the decade.
My husband and I debated this entire edit. He remembers what people actually wore, and I remember what retailers were asking customers to aspire to.
But who gets to define a decade? The average closet, or the clothes we all wanted to own?
I was twelve in 1996, young enough for Limited Too, but old enough to think that Contempo Casuals was the height of sophistication. The average closet may have held flannel and oversized denim, but the pages of fashion magazines were selling a cleaner, more refined point of view. Did you ever imagine that thirty years later, you’d be shopping like you still have a Contempo Casuals gift card?
2006
The birth of the “It Girl.” Most would argue it belonged to Rachel Bilson, Sienna Miller, Nicole Richie, Paris Hilton, or Kate Moss. Pick your fighter.
Me? I’ll always argue there were two. The “It Girls.” The Olsen Twins.
They add attitude. They had grace. Two women who taught an entire generation that vintage belonged next to luxury.
From the streets to the red carpet, they had a formula: thrifted layers, boho dresses, skinny scarves, oversized sunglasses, men’s cardigans, stacks upon stacks of necklaces, slouchy designer handbags, scuffed ballet flats or sky-high Louboutins.
I was convinced that the fastest way to learn great style was transferring to NYU - the only curriculum that mattered. No one mastered the “high-low” edit quite like this powerhouse duo. Today, the best-curated assortments and the most covetable wardrobes are all built the same way: mixing pieces with a little history and something fresh.
2016
A decade of tension.
Billowy sweaters swallowed skinny jeans.
Feminine dressing toughened up with a moto jacket.
Simple A-line dresses paired best with a gigantic bobbled necklace.
But the biggest tension of all? The rise of social media. We loved it for the inspiration, but we hated it for the comparison. And yet, we kept scrolling.
At 32, I was one of the last people with a death grip on my BlackBerry, convinced I never needed the iPhone. But eventually my fashion discoveries lived in my hands. My feed. Jenna Lyons walked so I could run. She made sequins and camo feel less like opposites and more like a distinct point of view.
2026
We are more than halfway through the decade, so how will you remember it?
For the first time in decades, there isn’t one right answer.
Individuality. Ownership. Authenticity.
It’s similar to the concept I explored last week in my newsletter. The strongest styles often come from rediscovering the one thing no one else can copy - your own archive.
We no longer want to be defined by one uniform, one icon, or one formula.
For Emily Grady Dodge, her, “big picture” is built the same way. The objects she wants to keep, the outfits she wants to repeat, and the rooms she wants to design all work towards her greater vision of life.
Our wardrobes shouldn’t be one perfect version of yourself. It’s about making space for every version that came before.
Or as Jordyn Sharfe recently shared.
I have always been guided by the idea that each thing you do leads to the next. Each version of yourself is an important piece of the next version of yourself, and all the versions of yourself make you human.
Here’s what’s currently hanging in my closet and how I like to dress when I work from home. The version of the decade I hope to remember.
I absolutely love this.
lol! Was just telling someone I want something that’s crushed velvet and then I immediately started remembering all my crushed velvet clothes from 1997… GAH! What a fun walk down memory lane :) and thank you for the shout out!!