MomSkoop
Fashion trends come and go, but certain handbags never truly disappear—they just take a breather before roaring back into the spotlight.
As we move into 2026, the fashion world is buzzing about classic bags that defined past decades and are now ready to reclaim their throne.
From Y2K icons to early 2000s boho beauties, these twelve legendary handbags are poised to become the most coveted accessories of the year.
1. Chloé Paddington
Remember when everyone wanted that puffy, padlock-adorned bag hanging on their arm?
The Chloé Paddington defined mid-2000s boho chic with its soft leather and signature brass lock.
Celebrities and fashion editors couldn’t get enough of its slouchy silhouette and luxurious feel.
Fast forward to 2026, and this beauty is celebrating its 20th anniversary with renewed excitement.
The fashion world loves a good throwback, and the Paddington’s return feels perfectly timed with our current obsession with early-2000s style.
Expect to see updated colors and materials while the iconic shape stays true to the original.
Whether you’re a longtime fan or discovering it for the first time, this bag brings instant vintage cool to any outfit.
2. Dior La Cigale
Jonathan Anderson has taken the reins at Dior, and fashion insiders are going wild over his fresh vision.
Enter La Cigale, a brand-new silhouette that’s already being called the next Dior It bag.
Anderson’s reputation for creating instant classics at Loewe has everyone paying attention.
The name means “cicada” in French, hinting at something elegant yet unexpected.
Early runway appearances show a structured yet playful design that balances Dior’s heritage with modern edge.
While technically new, La Cigale channels the spirit of iconic Dior bags from decades past.
Its rapid rise in popularity suggests this could be the defining handbag purchase of 2026.
Fashion editors are already adding it to their must-have lists for spring collections.
3. Coach Kisslock Barrel
Coach is digging deep into its archives, and the results are spectacular.
The Kisslock Barrel bag originally debuted in the 1970s when Coach was known for simple, durable American leather goods.
That distinctive metal clasp closure—the kisslock—makes opening and closing the bag satisfyingly tactile.
Reissued for 2026, this vintage-inspired piece is already flying off shelves faster than Coach can restock them.
The barrel shape offers surprising room inside while maintaining a compact, ladylike exterior.
What makes this comeback special is how it represents Coach’s heritage before logos took over.
People crave authentic, well-made pieces with history, and the Kisslock Barrel delivers exactly that with timeless appeal and accessible luxury pricing.
4. Chanel Classic Flap (90s-Inspired Update)
Chanel’s Classic Flap has been an icon since the 1950s, but the brand is giving it a distinctly 1990s twist for 2026.
Think softer leathers, slightly puffier quilting, and that effortless supermodel vibe that defined late-90s fashion.
The interlocking CC logo remains, but everything feels a touch more relaxed.
Early 2026 collections show this updated version dominating fashion weeks and celebrity street style.
The 90s were peak Chanel cool—Kate Moss, Naomi Campbell, and Linda Evangelista made these bags legendary.
By channeling that era’s energy, Chanel is capturing both nostalgia and modern sophistication.
Whether you choose classic black or experiment with updated colors, this reimagined heritage piece proves some designs only get better with time.
5. Balenciaga Le City
Few bags capture early-2000s cool quite like the Balenciaga City.
With its slouchy leather, studded hardware, and rock-and-roll edge, it became the ultimate off-duty model accessory.
Nicole Richie and Mary-Kate Olsen made theirs famous, carrying them everywhere from coffee runs to red carpets.
The City’s renaissance started a couple years ago and shows no signs of slowing down in 2026.
Modern fashion lovers appreciate its casual-yet-luxe vibe that pairs perfectly with everything from jeans to slip dresses.
Balenciaga has reissued the bag in fresh colors alongside classic black, giving new generations their chance to own this legend.
The distressed leather only looks better with age, making each City bag uniquely yours over time.
6. Dior Saddle Bag
John Galliano’s genius gave us the Dior Saddle Bag in 1999, and it immediately became a cultural phenomenon.
Its curved shape mimics an actual horse saddle, creating an instantly recognizable silhouette that looks amazing worn crossbody or tucked under your arm.
The early 2000s belonged to this bag.
After a hiatus, Dior brought back the Saddle a few years ago, and it continues riding high into 2026.
Celebrities like Bella Hadid and Blackpink’s Jisoo have kept it firmly in the spotlight with countless paparazzi moments.
What keeps the Saddle relevant is its perfect blend of quirky and sophisticated.
Available in endless variations—from classic logo canvas to exotic leathers—there’s a Saddle for every style personality and budget level.
7. Chanel 25
While everyone talks about the Classic Flap, Chanel insiders are obsessed with the newer 25 silhouette.
Named for its 25-centimeter width, this bag offers a fresh alternative to Chanel’s traditional shapes while maintaining that unmistakable luxury DNA.
It’s compact without being tiny, structured yet still soft.
Spring 2026 runway shows featured the 25 prominently, signaling Chanel’s confidence in this design.
Fashion bloggers and influencers have quickly made it their go-to for creating elevated everyday looks.
The 25 represents where Chanel is headed—honoring heritage while embracing contemporary needs.
Its versatile size works for day or evening, and the range of colors and materials means you can express personal style while carrying an instant status symbol on your shoulder.
8. Saint Laurent Mombasa
Tom Ford’s era at Yves Saint Laurent produced countless masterpieces, and the Mombasa bag stands among his greatest hits.
Launched in the early 2000s, this slouchy, oversized hobo featured distinctive horn detailing and buttery soft leather that felt like luxury personified.
It screamed effortless sophistication.
For 2026, Saint Laurent is reissuing the Mombasa, much to the delight of fashion historians and trend-forward shoppers alike.
The timing couldn’t be better as oversized, unstructured bags are replacing rigid, logo-heavy styles.
Named after the Kenyan coastal city, the Mombasa brings exotic glamour to everyday life.
Its generous size accommodates modern essentials like laptops and water bottles while maintaining an elegant drape.
Expect waiting lists when this beauty officially drops in stores nationwide.
9. Celine Phantom / New Luggage
Phoebe Philo’s Celine era gave us some of the most influential bags of the 2010s, but their roots trace back to Y2K aesthetics.
The Phantom and Luggage bags, with their architectural shapes and minimalist hardware, became the thinking woman’s status symbol.
No giant logos needed—the distinctive silhouette said everything.
These bags are experiencing renewed interest as fashion cycles back to understated luxury.
Their boxy shapes and sturdy construction feel refreshingly practical compared to delicate, decorative bags that dominated recently.
Celine’s current collections hint at bringing back elements of these classics, sparking excitement among longtime fans.
Whether you hunt down vintage versions or wait for official reissues, owning a Phantom or Luggage bag signals serious fashion credibility and timeless taste.
10. Louis Vuitton Murakami (Takashi Murakami Collab)
When Louis Vuitton teamed up with Japanese artist Takashi Murakami in 2003, they created fashion history.
The multicolor monogram and playful cherry blossom designs transformed classic LV bags into wearable art.
Suddenly, handbags became collectibles, and waiting lists stretched for months.
Jessica Simpson and Gwen Stefani made these bags camera-ready essentials.
Twenty-plus years later, these collaboration pieces are showing up again at vintage boutiques and resale platforms, commanding impressive prices.
The nostalgic appeal of early-2000s pop culture has made Murakami LVs highly desirable among younger collectors discovering them for the first time.
While Louis Vuitton hasn’t announced official reissues, the secondary market is booming.
Owning a Murakami piece means holding a slice of fashion history—when collaborations were still novel and genuinely exciting.
11. Fendi Spy Bag
Silvia Venturini Fendi designed the Spy Bag in 2005, and it immediately became one of the decade’s most talked-about accessories.
With its unique curved handles, hidden compartments, and luxurious nappa leather, the Spy felt like a secret agent’s stylish companion.
The craftsmanship required to make each bag was extraordinary.
After years out of production, the Spy is returning to prominence thanks to celebrity sightings and vintage fashion enthusiasm.
Hailey Bieber and Dua Lipa have been spotted carrying vintage Spy bags, instantly reigniting demand.
What makes the Spy special is its unconventional beauty—it doesn’t follow typical handbag rules, which is exactly why it stands out.
For 2026, expect both vintage hunting and possible Fendi reissues as this cult favorite reclaims its rightful place among iconic handbags.
12. Louis Vuitton Speedy (Classic)
Audrey Hepburn requested a smaller version of Louis Vuitton’s Keepall travel bag, and the Speedy was born in 1965.
This compact, dome-shaped bag has remained a brand staple for nearly six decades, appearing in countless movies, music videos, and street style photos.
Its monogram canvas is instantly recognizable worldwide.
The Speedy is experiencing fresh momentum as part of 2026’s early-millennium classics revival.
New generations are discovering what their mothers and grandmothers already knew—this bag combines practicality with timeless elegance like few others can.
Available in multiple sizes and materials, from classic monogram to colorful Epi leather, there’s a Speedy for everyone.
It represents accessible luxury and smart investment buying, holding value while serving you faithfully for decades of daily use.