The Many Bags of Jessica Simpson, Part Two

The pop star-turned-shoe mogul has a collection of bags that's as unique as it is enviable

I find Jessica Simpson sort of fascinating. I loved Newlyweds when it aired and think she has a great voice, and she parlayed all that into a billion-dollar shoe and accessory empire that sells zillions of girls their first pair of heels. After a very public divorce, she’s gone on to business success, a hot husband who’s seemingly always at her side and two cute kids. I respect her hustle.

The paparazzi don’t even seem to bother her when she’s at home in California all that much–we mostly get a glimpse at her enormous collection of designer bags when she’s at the airport or in New York for business. That’s why it’s taken us a long time to put together a sequel to Jessica’s first Many Bags, which we published all the way back in 2012. It’s been worth the wait, though–Ms. Simpson tends to eschew the Hermès and Chanel bags loved by many of her blonde bombshell compatriots in favor of an eclectic mix from other high-end brands. Check out a bunch of the best of them below!

Alexander McQueen Box Clutch
$1,668 via farfetch.com

As you’ll notice, Jessica far prefers huge bags to the cute little minis that have been popular over the past couple years. This is easily the smallest bag we caught her carrying.

Céline Edge Bag
Shop Céline Bags via Vestiaire Collective

This bag, with its slouchy shape and roomy interior, is much more her speed.

Céline Phantom Luggage Tote
Shop Céline Bags via Vestiaire Collective

The Céline Phantom Luggage Tote isn’t as omnipresent as it was a couple years ago, but Jessica seems to have gotten her first one recently–these photos are from only a couple days ago.

Céline Triptyque Bag
Shop Céline Bags via Vestiaire Collective

Céline bags aren’t new to Jessica, though–she’s been carrying the brand for years, including plenty of its less well-known designs.

Chloé Alice Bag
Shop Chloé via MATCHESFASHION.COM

Jessica’s one of us: a true bag lover, not just someone who carries whatever a brand send her for free or a stylist puts in her closet. That means you sometimes see her with a throwback, like this Chloé bag.

Dolce & Gabbana Sicily Bag
$2,945 via Neiman Marcus

For Jessica, this counts as a very small bag.

Dolce & Gabbana Sicily Bag
$3,395 via Nordstrom

This bigger version is much closer to her normal preferences.

Fendi Monster Zip Wallet
$1,050 via Bergdorf Goodman

We’re not counting this as a small bag because it’s technically a wallet, and I’d bet considerable money that her giant bag was waiting with her driver.

Fendi Painted Peekaboo Bag
Shop Fendi Bags via Nordstrom

Perhaps a giant bag similar to this one. (She’s partial to Peekaboos.)

Fendi Peekaboo Bag
Shop Fendi Bags via Nordstrom

VERY partial.

Fendi Whipstitch Peekaboo Bag
$4,900 via Barneys

And the bigger and more expensive, the better.

Givenchy Easy Tote
Shop Givenchy via Nordstrom

Givenchy no longer makes this bag, which is a bummer because it was accessible priced and very functional. I like it just as much as Jessica does.

Givenchy Pandora Bag
$1,990 via Nordstrom

Jessica seems a little less enthusiastic about this Givenchy bag; she carried her Easy Tote many times over the years, but the Pandora only made one appearance we could find.

Lanvin Tassel Tote
$1,550 via MATCHESFASHION.COM

The nice thing about preferring big handbags is they all make great carry-ons.

Marni Hobo
$1,610 via Barneys

Marni’s overall aesthetic tends to be very far from Jessica’s ultra-glam, ultra-femme look, but her appreciation of their handbags (she’s carried many over the years) really demonstrates how versatile a good bag is.