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Jessica Simpson‘s namesake footwear, apparel and accessories brand is turning 20.
While you may know Simpson for her successful music career with hits like “I Wanna Love You Forever” and “A Public Affair,” the musician is also well-known for her fashion prowess. Simpson launched the brand in 2005 with an initial focus on footwear. Since then, it’s grown to include boho-inspired apparel and accessories. To celebrate 20 years, Simpson launched a limited-edition “2.0” line of shoes, apparel and accessories that encapsulate the brand’s legacy and Simpson’s love of boho fashions.
Simpson took to Instagram Sunday (Oct. 12) to celebrate the launch, snapping a photo of herself in the Stevie Flare Jeans in Milton from the 2.0 capsule. “I wore my new 20th anniversary @jessicasimpsonstyle jeans out shoppin’ today and got stopped damn near 20x with a compliment!!!” she wrote in the caption. “Made me smile! Thank y’all for makin’ my day at the mall.”
Below, we’ve compiled a few favorites from the 2.0 capsule that you can shop on Jessica Simpson’s website. Our picks include everyday shoulder bags, Simpson’s Instagrammable denim and head-turning footwear just in time to update your fall wardrobe.
Jessica Simpson 2.0 Stevie Flare Jeans in Milton
Flared denim with sparkling adornments.
What were those coveted jeans that had people stopping Simpson up to 20 times at the mall? It’s the Stevie Flare Jeans in Milton, currently retailing for $119. The bell-bottom style is extremely boho-inspired with a dark wash, high-rise and embroidered detailing affixed to the seat of the pants. Star hardware litters the hip in bronze and silver hues, making this denim reminiscent of Y2K styles Simpson has worn in the past. If the 2000s-esque adornments didn’t sell you, the denim is also made of a stretch fabric that gives these jeans a comfortable, non-restrictive fit.
Jessica Simpson 2.0 Zembitti Boot in Black
Black leather cowboy boots with gold accents.
Fall is here, which means it’s time to search for a boot that you’ll want to wear again and again. We think the Zembitti Boot might be your best bet. Retailing for $179, this western bootie is made of durable and glossy black patent leather with gilded accents throughout. The calf-length boot is also affixed with pointed toes and easy to walk in wedge heels standing at 2.6 inches.
Jessica Simpson 2.0 Palias Charm Pump in Black
A black pump with chain and charm adornments.
According to her website, this style is one of Simpson’s favorites, and it’s easy to see why. The Palias Charm Pump currently retails for $129 and comes with loads of whimsy. The basic black pump was updated with plenty of chains, charms and rhinestones, a maximalist’s dream. The silhouette also includes sleek pointed toes and 3.5 inch stiletto heels. The adornments make this piece a stand-out, and one we can see our readers wearing from the office to date night with ease.
Jessica Simpson 2.0 Grayson Shoulder Bag in Meteorite
A black east-to-west bag.
The east-to-west bag is an on-trend silhouette as of late and everyone’s taking note, including Simpson. The brand’s Grayson Shoulder Bag in Meteorite is a great example of an east-to-west bag, what with the elongated straps and bowling bag-esque construction. The bag is currently available for $108, on the more affordable side that we’ve seen for this style.
The Grayson is seemingly made out of patent leather, based on the bag’s shine, and comes equipped with a gold chain draped across the front affixed with little charms. Our motto? You can never have too many black bags, especially when fall rolls around. It’s a grungy and playful pick, and one we can see our readers getting lots of mileage out of.
Jessica Simpson 2.0 Claira Sherpa Moto Jacket in Black
A sherpa jacket in black.
Ready to cozy up? With the weather getting colder, it’s important to have a good jacket in your rotation that will keep you both warm and stylish. We think that the Claira Sherpa Moto Jacket in Black is a great pick for those reasons. The moto style is equipped with ultra-warm sherpa material in an off-white hue that lines the lapel and sleeves. The body of the jacket is made of a black distressed fabric. The jacket’s oversized fit is offset by the cropped composition, making it wearable, not too boxy. For $249, this jacket is an investment, but one worth the price tag to keep you fashionably cozy this fall.
Jessica Simpson 2.0 Bias Dress in Black
A black lace slip dress.
We’d like to nominate the Bias Dress in Black as our official “going out” dress for 2025. Whether you’re heading to dinner or hitting up the club to dance the night away, this dress is a great starting point. It’s a versatile offering with a flattering form-fit and lace trim. The piece offers endless styling possibilities, making it great for just about every scenario. Grabbing coffee? Dress the Bias down with a sweater layered over it. Celebrating a birthday? Wear it solo with platform pumps for a head-turning moment.