Let’s cut to the chase. Every year, fashion designers walk out onto the runway, take an exaggerated bow, and then claim they have invented something completely new or different; only to turn around and see that it has really just been done by 90s style icons decades earlier. Slip dresses. Oversized blazers. Baggy jeans. Chunky platform shoes. The 90’s have not really returned; they’ve just been waiting for everyone else to catch up.
At Itismandy.com, we are not only going to discuss what styles are currently trending—we will also be discussing why they are trending, who originally created them, and most importantly—how YOU (a fully aware person of 2026) can wear them in a way that feels like YOU vs. a costume. So strap in, folks, because we are heading back to the most creatively-expressive decade ever for fashion—the 90’s.
The Decade That Fashion Still Can’t Quit
The 90’s were chaotic, politically troublesome, culturally loud, and all-out-spectacular visually. Grunge kids sitting next to models wearing gorgeous satin slip dresses. Hip-hop artists redefining the meaning of ‘luxury’ while Calvin Klein stripped everything down to the bare essentials. It was probably one of the biggest contradictions of any decade which is why there are still so many people labeled ‘icons’ from that decade.
What made fashion in the 90’s so cool was not about perfection…Confidence was what it came down to. They dressed without worrying if they would be able to reach an algorithm to please someone. No one is trying to emulate a particular group, or style, or hit specific aesthetic because TikTok told them to dress a certain way. The people whose outfits you have seen — both women and men — are dressing for themselves and their own values, cultures, music, and moods. As a result, this self-focused way of dressing created the guide and foundation for everything that has been done since.
Kate Moss: The Original “I Woke Up Like This” Energy
If you are trying to understand the prevalence of the slip dress at your cousin’s wedding, brunch with friends, or the thousandth person wearing one to that concert next month, you have to start with Kate Moss. Discovered at age 14, she was the epitome of what was referred to in the 1990s as “effortless.” She would wear a satin slip styled in a bias cut, messy hair, and a leather jacket, and she wouldn’t have to explain to anyone why she was wearing that outfit.
Why She Still Matters Right Now
What Kate accomplished was building a philosophy versus a look. She created a style that required less effort but had the same level of intention to achieve success. Although she wore the most basic of items (e.g. her plain white t-shirt, black straight leg jeans, high-end satin/traditional slip dress and/or leather jacket) when you think about it, those items have become the most sought after outfits in very popular venues to date. The “Kate Moss approach” to clothing is also translated in 2026 into the minimalist wardrobe movement — ie you do not need every trending piece of clothing out there. You need the five most essential pieces that you have mastered how to wear. It was an incredibly radical notion when first introduced by Moss in 1994 as it is still just as radical today since few people are ready to commit to that style approach.
Naomi Campbell: The Standard Nobody Could Match
When Naomi Campbell entered a space it was as though she came in with an energy that electrified the whole room. She always had complete command of her environment, whether it was during a Versace fashion show, at a UNICEF gala, or at a random after-party in London. She had a skill for projecting an image while remaining absolutely confident in that image — a skill that most people will spend their lives hunting for — yet Campbell had it down to a science, so it was not only impressive but beautiful too.
Power Dressing Before It Was Called That
Naomi Campbell exemplified the core characteristics of power dressing — which are strong feminine characteristics; fierce; dramatic; and unapologetic. She wore clothing that demanded space. Boldly shaped silhouettes; dresses that made a statement; clothing that required a certain confidence to wear — Campbell wore them all and did so with perfected flair. Currently, in the year 2026, we are witnessing the re-emergence of power dressing through the resurgence of oversized tailoring, the resurgence of structured tailoring, and the understanding that utilising the space occupied by clothing is a demonstration of strength — as was proven by Campbell in 1993.
TLC: The Girls Who Made “Streetwear” a Legitimate Fashion Language
T-Boz; Left Eye; and Chilli created a fashion style that the fashion industry didn’t know how to classify at the time they made it. Each of them donned bright colours; oversized sweatsuits; unique colour-coordination/outfit combinations; and sport/bra top outfits — the trio merged the language of street style with high-fashion to create clothes that could be featured in high-fashion magazines. What makes TLC’ fashion accomplishments even more incredible is that the trio produced some of the finest music to have been produced during that particular time.
The Blueprint for Everything Gen Z Loves
To say that TLC didn’t receive their due credit for their style during their era isn’t entirely accurate, as the ladies themselves had a plan in creating and representing their identity and culture through their fashion choices, and how these choices ultimately influenced the evolution of streetwear as we know it today. The way Zendaya fluidly moves across both worlds of fashion and streetwear is largely due to the influence of TLC paving the way for people to do so; as well as the cropping and wide-leg pant styling from TLC. They were one of the most impactful fashion icons from that period in terms of the actual cultural impacts their style had on why people dress the way they do today, including how we dress in our everyday lives and not just on red carpets.
Aaliyah: The One Who Made Cool Look Effortless Before “Cool” Was a Vibe
Aaliyah, similar to TLC, plays a major part in the discussion regarding 90’s fashion, and did so by inherently blending streetwear styles with established feminine pieces. Examples would be cropped tops worn with low-rise track pants, and oversized Tommy-hilfiger pieces styled in such a way that made them visually appealing. Aaliyah would mix non-conventional pieces and made them universally accepted as fashion combinations.
The Aaliyah Effect on 2026 Dressing
What Aaliyah gave to us that we will incorporate into our dressing for the year of 2026 and on will be the fact that she granted us the permission to mix high-end, low-end, sporty, feminine, tough, soft pieces. The specific example that I would provide is of her famous yellow Tommy-hilfiger track-suit that was worn in 1997; it has been referenced, repeated, and re-mixed so many times that it has become a staple of any mood board that you could create. However, more important than any single piece that Aaliyah contributed to the world, was her granting us all permission to experiment and to create our own forms of identity/style.As we approach 2026, this isn’t only a styling tip but rather what we’ve discovered to be the basic premise of all things within this area. Currently, one of the most appealing types of clothing is the kinds of clothing that basically defy all reason/logic — and work (ie: an outfit as comprised by two totally disparate things that should have ‘never been seen together’ but they actually do look good together). Aaliyah had this tension figured out pretty much before the majority of us could even buy our clothes.
The Spice Girls: Five Different Women, One Massive Style Lesson
Unlike an outfit having only one look/feeling, the Spice Girls were comprised of five different women thus displaying five very different aesthetics (and that’s what we want you to take from this). Victoria Beckham’s classic black dress. Mel B’s animal prints and bold pieces of clothing. Emma Bunton’s baby pinks and platform shoes. Mel C’s tracksuit and crop tops. Geri Halliwell’s Union Jack dress. All of those outfits were bar-none, some of the first major pop culture examples of how you can have whatever individual stylistic aesthetic you want and still be included in a collective.
Girl Power Was Also a Fashion Manifesto
When the girls spoke about “having girl power,” they meant it in all areas — including having your own style not being defined by anyone other than yourself. All five Spice Girls had distinct visual identities but as a collective, were able to fill stadiums throughout the world (together). By extension, the message being communicated through this space (like it was communicated through the Spice Girls) is that your individualism with regard to your specific style is just as valid/valuable as by representing collective groups based on those same parameters.
Winona Ryder: The Dark Horse Who Started Gothic Chic
In 2026, while we’re all still figuring out how to dress for ourselves rather than to gratify others, the Spice Girls continue to deliver one of the best fashion lessons ever.
While everyone else chased supermodel minimalism and pop star indulgence in fashion in the ’90s, during those years, Winona Ryder quietly built what would become the most imitated style of the decade: dark, vintage, romantic, and a little undone. Black turtlenecks. High-waisted trousers. Thrifted layers. Heavy boots and delicate dresses. She made “cool girl” a personality — and a very good one.
Why This Matters More in 2026 Than Ever
The current gothic-glam fashion movement in runway shows and street style? Winona. The current trend of dark romanticism, blending vintage with modern day, and incorporating thrift culture as legitimate style curation? A straight line connects it to her. For Gen Z, who have grown up in the thrift shopping era and now wear it for identity rather than necessity, Winona Ryder’s fashion philosophy is as current as anything you have seen in the last three seasons.
What 2026 Actually Owes to the 90s
It’s not just about nostalgia, as the current millennial and Gen Z trends would suggest. Market research indicates that the entire vintage sector is a $75 billion industry in 2024, with predictions for it to double by 2032. The retail market for both Tommy Hilfiger, Calvin Klein, and Versace has launched collections based on archival references; and the desire to access the original product or as close to it as possible has become increasingly evident.
More than just economics, the 90s are the current reference for the true model of self-expression through style. The fashion icons of the 90s created their style and, thus, followed their own rules, not following trends. Kate Moss didn’t look to see what was trending before she put on her slip dress. Aaliyah didn’t need approval to create a new way of dressing for women by blending feminine pieces with streetwear. TLC didn’t wait for fashion to acknowledge the style they created.
The essence of fashion from the 90s is the individuality, confidence and defiance to be unapologetic about occupying fabric with your personal fashion expression. In 2026, with the demand for aesthetic perfection in order to fit in and be accepted like never before, the value associated with the heritage of the 90s is absolutely priceless.
Dress with conviction. Find out who led the way before you. Understand where the garments that you hold dear were created. And, ultimately, take those garments and create something new. Every person listed has done that. That’s the whole point.
