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Whether you’re already pulling together your tailgate menus or clinging to the final weeks of pool season, you probably have a few beverages in need of a cool place to hang out. From clever backpack designs and canvas totes to retro-inspired coolers, here are some of the best options to take you through the last days of summer and well into tailgating season!

Waxed Canvas Cooler Tote

This waxed canvas cooler tote is like the insulated version of your favorite fall jacket. The olive green canvas is tall enough for a bottle of wine, along with plenty of snacks. It has a protective wax coating that makes it incredibly durable — perfect for taking with you to football games and backyard watch parties. It can even be monogrammed for a traditional touch.

Brown monogrammed cooler
Mark & Graham Waxed Canvas Cooler Tote, $89 | Image: Mark & Graham

Eola Bucket Cooler Bag

This vegan leather bag looks sleek and minimalist, but it packs major storage. Holding up to 12 cans or two wine bottles and eight cans, the Eola Bucket Leather Bag from Corksicle will become your go-to cooler for picnics, tailgates, and beach days. Order it in one of seven sophisticated colors — including a vibrant turquoise, subtle slate blue, whimsical coral, or relaxing lavender.

Pastel blue cooler backpack
Eola Bucket Cooler Bag, $159.95 | Image: Corksicle

Luxe® Dual Compartment Backpack

This faux leather backpack combines a stylish look with major functionality. The Igloo Luxe® Dual Compartment Backpack holds up to 26 cans between its spacious main compartment and clever lower compartment. In rich cognac or minimalist black faux leather — both with gold details — this is the most discreet cooler you’ll ever carry.

Brown leather Igloo cooler
Igloo Luxe® Dual Compartment Backpack, $99.99 | Image: Igloo

Monogrammed Insulated Canvas Cooler

A darling monogram and striped straps make this monogrammed insulated canvas cooler from Marley Lilly one of the cutest coolers on the market. It holds up to 30 cans at once, or you could opt for several bottles of wine and a few snacks. With 14 different monogram styles and dozens of thread color options, this cooler makes for a fun housewarming or bridal shower gift ahead of tailgate season.

White and navy blue canvas cooler
Marley Lilly Monogrammed Insulated Canvas Cooler, on sale for $39.99 (reg. $49.99) | Image: Marley Lilly

Insulated Tote Bag

If you love the look of a classic canvas tote, L.L. Bean’s insulated take on their Boat and Tote is a must-have. Available in dark green, blue, or mineral red, L.L. Bean says this bag combines the insulation of their beloved lunch boxes with the look of their iconic totes. It holds up to 16.5 liters, giving you plenty of room to tote both snacks and beverages.

White and green LL Bean canvas tote bag
Insulated Medium Tote Bag, on sale for $59.99 (reg. $69) | Image: L.L. Bean

Retro Picnic Basket 25 Qt Cooler

Just looking at the neon colors of this retro picnic basket cooler has us reminiscing about Saved by the Bell and Mall Madness. Thirty-six cans fit into this ’90s flashback cooler, and the fuchsia, teal, and bright yellow combination is vintage perfection. This classic hard-sided cooler will be your go-to for tailgates, boat days, and backyard parties on that first nice day of fall.

Retro cooler
Igloo Retro Picnic Basket 25 Qt Cooler, $49.99 | Image: Igloo

YETI Roadie Wheeled Cooler

YETI is the gold standard in coolers these days, and if you are in the market for a splurge, it’s well worth it. This hard-sided cooler can maintain ice for several days, even in hot weather. This wheeled version helps make it easier to transport this notoriously heavy brand. Plus, it holds up to 42 cans, making it a great choice for a weekend-long party.

Navy blue YETI cooler on wheels
YETI Roadie 48 Wheeled Cooler with Retractable Periscope Handle, $450 | Image: Amazon

Cooler Caddy

Fanny packs are still on trend, so what’s better than combining a fanny pack and a cooler? This cooler belt bag attaches to your belt or a larger tote and comfortably fits six cans. Plus, it’s made of a durable polyester and nylon blend, so it’s ready for all your fall adventures.

Fanny pack cooler
Bellroy Cooler Caddy, $59 | Image: Nordstrom

Cooler Duffle Bag

This bag’s autumnal colors and paisley print are perfect for all the events on your fall calendar. From football tailgates to fall festivals and apple picking, you can carry your favorite snacks and beverages in this roomy and insulated duffel bag. It also comes in a classic black stripe, a fresh pink stripe, and a vintage-inspired yellow.

Patterned cooler bag
Premium Cooler Duffel Bag, $79 | Image: Nordstrom

Chillpod™ 25 Quart Hard Cooler

Want a Barbie pink cooler to stand out this tailgate season? The Corksicle Chillpod™ is one of the most eye-catching coolers on the market, with a space-age-inspired silhouette. It fits up to 32 cans, has a top designed to function as a table, and has a storage divider that doubles as a cutting board and bottle opener. It’s the Swiss army knife of coolers and keeps ice for multiple days. If pink isn’t for you, it also comes in white and lilac.

Pink Corkcicle cooler
Corksicle Chillpod 25 Quart Hard Cooler, on sale for $188.97 (reg. $269.95) | Image: Corksicle


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About the Author
Heather Bien

Heather Bien is a Southern writer, Richmond native, and aspiring gardener. She loves small-town travel and homemade lattes.