Specialist Picks: Shop the Best Chanel Bags to Buy Now
From oversized totes to retro bowlers and slouchy hobos, discover the Chanel bags finding new relevance for fall, plus burgundy and exotic styles.
Fall’s biggest handbag trends are making a case for more volume, softer shapes and a return to styles that once defined earlier fashion eras. Oversized totes are back in rotation, slouchy hobos have replaced some of the more structured silhouettes of recent seasons and retro bowling bags are finding a new audience. Burgundy remains a key color for fall, while exotic skins bring another layer of texture to the season.
This month, our specialists selected five Chanel bags that capture these shifts through designs spanning the late 1980s through the 2010s. A graffiti-covered On The Pavement messenger offers an oversized, unstructured take on the tote trend, while a 1995 bowler revisits the dome-shaped bags returning now. A burgundy alligator Classic Flap and relaxed brown hobo bring fall color and texture into the edit, and an XXL Grand Shopping Tote makes the case for going bigger. Together, the selection shows how earlier Chanel bags can take on new relevance as silhouettes and materials cycle back into fashion.
Oversized Totes: Chanel Black Quilted Caviar Supermodel Weekender XXL Grand Shopping Tote, $6,200
Bigger bags are firmly back in the conversation for fall, and the Chanel Black Quilted Caviar Supermodel Weekender XXL Grand Shopping Tote from 2003-2004 takes the trend to an exaggerated scale. Measuring 18 inches wide, the bag has the capacity expected of a weekender but retains defining Chanel details through black quilted caviar leather and gold hardware.
Its generous proportions feel especially relevant as fashion moves away from bags designed to hold little more than the essentials. The wide body and long shoulder straps make this a true carryall, with enough room for everyday necessities, a laptop or the extra layers that come with fall dressing. More than two decades after it was made, the XXL format feels right in step with the renewed appetite for bags that prioritize both scale and utility.
Retro Bowler: Chanel Vintage Black and White Quilted Calfskin Letter Logo Large Bowler Duffle Bag, $6,200
Bowling bags are having another fashion moment, bringing the structured, dome-shaped silhouettes of past decades back into focus. The Chanel Vintage Black and White Quilted Calfskin Letter Logo Large Bowler Duffle Bag from 1995 offers an especially bold interpretation. Its elongated body and dual top handles establish the retro shape, while oversized white Chanel lettering breaks across the black quilted calfskin.
The proportions give this bag much of its renewed relevance. It has the structured curve associated with classic bowling bags but at a larger scale that also speaks to the move toward roomier styles this fall. Nearly three decades after its debut, the combination of a practical duffle shape and graphic 1990s branding makes this vintage Chanel feel closely connected to the season’s revival of retro handbag silhouettes.
Hobo Styles: Chanel Brown Quilted Lambskin Medium Trendy Pockets Hobo, $6,800
Slouchier bags are returning alongside fall’s oversized styles, bringing a softer approach to everyday dressing. The Chanel Brown Quilted Lambskin Medium Trendy Pockets Hobo captures that shift with a relaxed shape designed to sit naturally against the body. Quilted brown lambskin gives the bag a rich seasonal tone, while aged gold hardware adds warmth without making the overall look feel too polished.
The silhouette is what makes this Chanel feel especially current. Its curved profile and easy shoulder carry align with the renewed interest in hobos and crescent-shaped bags, while multiple exterior pockets add a practical element to the design. Rather than holding a rigid shape, the soft lambskin allows the bag to feel more relaxed with wear, making it an appealing counterpoint to Chanel’s more structured flap bags.
Burgundy Croc: Chanel Vintage Burgundy Alligator Small Classic Double Flap Bag, $14,900
Burgundy continues to carry momentum into fall, moving beyond ready-to-wear into accessories in deep wine and oxblood tones. The Chanel Vintage Burgundy Alligator Small Classic Double Flap Bag from 1989-1991 pairs the season’s standout color with alligator, another material moving back into the fashion conversation. Its glossy surface gives the burgundy greater depth, while gold hardware brings out the warmer undertones of the color.
The small Classic Flap also offers a counterpoint to the oversized and slouchy silhouettes elsewhere in this edit. Its structured shape keeps the focus on the richness of the alligator and color, showing that fall’s handbag trends are not exclusively about scale. Dating to the turn of the 1990s, this vintage example feels remarkably aligned with the darker palette and polished exotic finishes returning this season.
Oversized Soft Totes: Chanel Multicolor Graffiti Tweed and Khaki Toile On The Pavement Large Messenger Bag, $21,300
The Chanel Multicolor Graffiti Tweed and Khaki Toile On The Pavement Large Messenger Bag from 2015 takes fall’s move toward bigger bags in a softer, less conventional direction. Rather than relying on a structured tote shape, the oversized messenger has a relaxed construction that allows the bag to fold and drape as it is carried. Khaki toile and multicolor tweed add texture, while the graffiti-style treatment gives the surface a deliberately layered look.
Part of Chanel’s On The Pavement collection, the bag reflects the street-art influence that made these designs such distinctive pieces from the period. Its generous proportions feel newly relevant as oversized bags return, but the appeal goes beyond size alone. The combination of an unstructured silhouette and expressive surface treatment offers a more eclectic alternative to a traditional Chanel carryall, making this one of the most directional picks in the September edit.
Chanel Bags for Fall
This September edit reflects a broader shift in handbag fashion toward pieces with more presence and personality. Larger proportions and softer construction are changing the way everyday bags are being worn, while the return of bowling and hobo silhouettes has brought earlier Chanel styles back into focus. Burgundy and exotic skins add a richer material direction that feels especially suited to the season.
Looking beyond recent collections also reveals just how many of these ideas have appeared in Chanel bags before. A 1990s bowler can speak directly to a shape gaining momentum today, just as an oversized tote from the early 2000s can feel newly relevant as smaller bags give way to more generous proportions. The September selection offers a reminder that some of the most compelling bags for fall may already be waiting on the secondary market.
Buy and Sell Chanel Bags with Sotheby’s
Whether you're a seasoned collector or new to the world of luxury handbags, Sotheby’s offers a trusted, seamless way to buy and sell Chanel bags on the secondary market.
Why Choose Sotheby’s?
- Expertly Vetted Selection
Explore rare and iconic Chanel bags, from Micro Mini Flaps starting around $3,000 to highly sought-after limited-edition and collectible pieces ranging from $15,000 to $45,000. - Exclusive Global Access
Shop Chanel bags through auctions and Buy Now marketplace, backed by a worldwide network of collectors and consignors. - Flexible Ways to Buy
Purchase online or in person at our locations in New York, Paris, and Hong Kong—or work with a dedicated handbags concierge. - Exceptional Value
Every bag is authenticated and priced by Sotheby’s specialists to reflect true market value. - Constantly Evolving Inventory
Discover classic Flap and Mini Flap bags, rare colorways, and limited-edition pieces, with new inventory added regularly.
Ready to Get Started?
- Browse Sotheby's upcoming handbag auctions in New York, London, Switzerland, Paris, and Hong Kong
- Shop Sotheby's Buy Now Chanel bags for instant access to available inventory
- Speak with a Sotheby's handbags specialist to consign or request a valuation for a Chanel bag
Trust our worldwide network of leading luxury specialists from a globally renowned auction house established in 1744.
