The Olsen Twins: Shaping Fashion for Decades
How Mary-Kate and Ashley Have Pushed Boundaries and Rewritten the Style Rulebook
In fashion history, there's no shortage of iconic style muses. The most obvious muses that come to mind instantly are Iris Apfel, Jane Birkin, Audrey Hepburn, and Grace Kelly. Each of these muses has not only defined an era but continues to influence the way we approach fashion today. But some fashion icons, while less obvious, deserve just as much recognition.
of Long Live Substack recently shared her love for Paul Newman as her ultimate style inspiration.
However, it’s always been the Olsen twins for me.
For starters, Mary-Kate, Ashley, and I are all bite-sized. In my head, we were best friends, bonding over the struggle of being overlooked or underestimated for our size.
Secondly, I was desperate to replicate any outfit from their straight-to-VHS cult classics (Winning London and Passport to Paris), or their short-lived TV show So Little Time, but I always came up empty-handed in the kids’ section of every store.
Finally, their style has never stayed static — it’s evolved with them, constantly shifting and always reflecting personal growth.
connected recently with the Olsen’s vintage dealer of many years and nails my sentiment perfectly:
“For a generation — women my age — the Olsen twins have *remained* consistent style icons since they were children, then teens/20s, then adults as designers. Despite what they’re known for, and their personal styles, evolving! That is truly something.”
From child stars to founders of one of today’s most influential luxury brands, The Row, their fashion journey mirrors their evolution. It’s a journey worth diving into deeper, especially as we’re currently stuck on the hamster wheel of winter (barely survived January), dreaming of spring and the warmer months ahead.
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Effortlessly Coordinated with Adult Flair
A milestone that feels surreal: the fashion moguls will turn 40 next June (excuse me, what?!?!). But before we jump decades ahead, let’s rewind to the '90s, when they first hit the red carpets.
Early on, their twin styling was a masterclass in coordination—always synced, but never identical. They embraced iconic '90s pieces, exuding effortless cool in lace-trimmed prairie sets or satin ensembles. Their outfits balanced girly details with a touch of edge, pairing delicate pieces with chunky loafers, chokers, or sleek accessories. Every so often, their youth peeked through—mostly on the covers of their VHS tapes. Think overalls, bucket hats, and bold primary colors. More often than not, though, their looks seemed straight out of a grown-up's wardrobe.
Two Steps Ahead (Or Is it Four Steps? 😂)
Ahead of the curve in the ‘90s, the Olsens’ style borrowed from adults early on —something that children’s fashion is now fully embracing. I recently wrote about brands like Bobo Choses or Tiny Cottons making waves in this space. For those with kids, take a cue from your favorite pair and snag a dress or trousers from these brands, which are capturing this trend perfectly.
The Highs and Lows of it All
As they matured, their styles became a reflection of their personalities—Mary-Kate’s bohemian nonchalance, Ashley’s sleek refinement. Different yet complementary, their signature was mastering the art of contrast, effortlessly blending vintage with designer and casual with high-end. This instinct for contrast extended beyond their closets and into their business ventures. In 2004, their Walmart diffusion line made chic design accessible — another stark contrast to their luxury shopping habits, but a move that proved visionary. Ahead of the curve yet again before Target’s Proenza Schouler and Rodarte collaborations redefined high-low fashion.
Shaping the Future
The biggest contrast of all was in their play on proportions. With an intuitive sense of balance, they paired oversized silhouettes with sleek tailoring, creating looks that were meticulously crafted. Long before it became a fashion mainstay, they redefined shape and volume in a way that set them apart from others their age. Their influence on contrast and oversized dressing remains undeniable today, with brands like Tibi carrying the torch. Proportion play with a modern twist defines Tibi's aesthetic. Season after season, their looks strike a refined balance of volume and structure, edgy yet delicate, intentionally designed, and instantly wearable.
By the latter half of the 2000s, a secret sauce was brewing—one that would set them on a path to an entirely new stratosphere. Their focus shifted from personal style to building a legacy.
The Beauty of Holding Back
As their style evolved into their 30s, the Olsens moved away from the layered eclecticism of the 2000s, embracing a more refined, monastic approach—a true reflection of their maturity. Their wardrobes became a study in restraint—favoring muted palettes, fluid tailoring, and the quiet confidence of well-chosen textures over statement pieces.
Silhouettes remained oversized but felt more intentional, accessories were minimal yet impactful, and luxury was no longer about excess but precision. Their appearances became increasingly rare, but when they did step out—whether in impeccably draped coats, loosely structured suits, or floor-length dresses in whisper-soft fabrics—their presence was unmistakable. This shift wasn’t just a departure from their past—it was a redefinition of modern elegance. One that became the foundation of their fashion brand The Row and proving that the boldest statement often comes from knowing when to hold back.
The New Faces of Luxury
The Olsen Twins and The Row didn’t define quiet luxury, but they undeniably shaped its modern iteration. The concept has long been rooted in the old-money aesthetics and impeccable craftsmanship of brands like Loro Piana, Brunello Cucinelli, and Hermès. However, The Row set the standard for contemporary minimalism. Today, countless brands attempt to emulate its aesthetic, from mid-tier labels like Toteme to Madewell, which has subtly shifted its creative direction with nods to minimalism. Even
The Found Journal Substack provides advice on how to dress like The Row on a budget.
There is no denying Mary-Kate and Ashley’s undeniable influence (they’ve even amassed a mirage of accolades) extends far beyond designing a cool, hip brand of the 21st century. They have redefined the blueprint for modern luxury.
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The Unstoppable Trailblazers
As the Olsens approach their next milestone chapter, it's fun to consider where their journey will lead them next. From their coordinated energy of the ‘90s to the contrasts of proportions in the 2000s, their style has always been a reflection of their evolving personal growth. Now, with a more refined, minimalist approach in their 30s, will they continue to innovate within the luxury space, or perhaps venture into new creative territories? Whatever comes next, their forward-thinking ability for trends ensures their influence will remain profound.
Our Lips and Sealed and So Little Time were some of my favorites. I was always so confused why I couldn't find anything like what Mary Kate and Ashley were wearing when I went shopping - I'm glad it wasn't just me :)