Entertainment
Jessica Simpson’s Clothing Brand Turns 20: Shop Our Favorites From the Anniversary Collection

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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.
Entertainment
Sombr & Olivia Dean to Make ‘Saturday Night Live’ Debuts, With Glen Powell Set to Host for First Time

A few of music’s biggest rising stars are getting big breaks this fall, with Saturday Night Live announcing Friday (Oct. 17) that Sombr and Olivia Dean will make their musical guest debuts on upcoming episodes.
Sombr will perform on the episode airing Nov. 8, which Nikki Glaser will host. The week prior, Miles Teller will helm an episode airing Nov. 1, with Brandi Carlile serving as musical guest for the third time in her career.
Then, Dean will perform at 30 Rock on Nov. 15. Teller’s Top Gun: Maverick costar Glen Powell is set to host for the first time.
The news comes as both Sombr and Dean’s careers are taking off. The former’s breakout hit “Back to Friends” made him a Gen Z alt-pop sensation, peaking at No. 22 on the Billboard Hot 100. He’s currently riding the success of his debut album, I Barely Know Her, which helped propel him to No. 1 on the Billboard Hot 100 Songwriter’s Chart.
The latter is one of the most promising singer-songwriters of 2025, earning critical acclaim for her new album, The Art of Loving. So far, the project has reached a peak of No. 7 on the Billboard 200, and Dean is currently on tour in support of the LP.
The trio of new musical guest announcements mark just the latest stars SNL has booked for this season. This weekend, Sabrina Carpenter will make her debut as host in addition to performing tracks from her Billboard 200-topping album Man’s Best Friend.
Bad Bunny also returned to SNL to host for a second time on Oct. 4, while Role Model recently made his musical guest debut.
Entertainment
Taylor Swift Dominates U.K. Albums & Singles Charts for Second Consecutive Week

Taylor Swift has retained the top spots on the U.K.’s Official Albums and Singles charts for a second consecutive week on the tallies dated Friday (Oct. 17).
The Life of a Showgirl holds on to the top spot on the Albums chart, while its lead single, “The Fate of Ophelia,” extends its stay at the summit of the Singles chart for a second consecutive week. The latter is the first time in three years that one of Swift’s singles has enjoyed a run of multiple weeks in the top spot. “Anti-Hero” from 2022’s Midnights earned six weeks at No. 1, while “Fortnight” (2024) and “Is It Over Now?” (2023) lasted just a single week.
The Life of a Showgirl broke numerous records on its way to No. 1 in the U.K. The record had the fastest selling opening week (423,00 units) since Ed Sheeran’s 2017 LP Divide (672,000). It also became the fastest selling album on vinyl this century in the U.K., and fastest ever since records modern Official Chart records began in 1994.
The Life of a Showgirl is her 14th U.K. No. 1 album; she also extends her lead with the most No. 1s on the U.K. Albums Chart for an international artist, and is tied for second overall with The Rolling Stones (14). The top spot is also currently a tie between The Beatles and Robbie Williams, who both have 15 apiece.
Olivia Dean takes the runner-up spot on both the Official Albums Chart and Singles Chart with The Art of Loving and its breakout song, “Man I Need,” both topping out at No. 2. Earlier this month, Dean achieved a rare double for a British artist with No. 1s on the aforementioned charts.
Fresh off his Oasis support slots, former Verve frontman Richard Ashcroft earns the No. 3 spot on the Official Albums Chart with Lovin’ You. Sabrina Carpenter’s Man’s Best Friend closes at No. 4, and The Weeknd’s greatest hits compilation The Highlights lands at No. 5.
On the Singles Chart, “Golden” from KPop Demon Hunters ends the week at No. 3, having already enjoyed an eight-week run at the summit. Swift’s “Opalite” (No. 4) and “Elizabeth Taylor” (No. 6) continue to see success, while RAYE’s “Where Is My Husband!” lifts one place to No. 5.
Entertainment
Morgan Wallen Notches Fifth Country Airplay No. 1 From ‘I’m the Problem’ With ‘I Got Better’

Morgan Wallen delivers his 19th career No. 1 on Billboard’s Country Airplay chart as “I Got Better” rises two spots to top the Oct. 25-dated survey, up 13% to 32.7 million audience impressions Oct. 10-16, according to Luminate.
The Joey Moi-produced single — with seven cowriters including Wallen, Ernest, HARDY and Blake Pendergrass — becomes the fifth No. 1 from Wallen’s album I’m the Problem, released in May. One more chart-topper from the set and he’d match the six from his 2023 LP, One Thing at a Time, which remains tied for the one-album record (discounting deluxe editions) with Luke Bryan’s 2015 Kill the Lights.
Boosting the profile of “I Got Better,” its official video premiered Oct. 1.
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I’m the Problem has led Billboard’s Top Country Albums chart for its first 21 weeks, followed at Nos. 2 and 3, respectively, on the Oct. 18-dated ranking by One Thing at a Time and Wallen’s 2021 release, Dangerous: The Double Album. Together, the three projects form one of the most formidable runs in modern country music history, combining for 205 weeks at No. 1 (with a record 97 frames at the summit belonging to Dangerous).
Before topping Country Airplay, “I Got Better” completed a full-format sweep, hitting No. 1 on the Oct. 18 Hot Country Songs chart thanks to 13.2 million official U.S. streams, 31 million in radio audience and 1,000 sold. The win gave I’m the Problem four leaders on the list, equaling the output of One Thing at a Time.
Above the Chimney Tops
Lainey Wilson breaks into the Country Airplay top 10 (12-10) with “Somewhere Over Laredo” rising 9% to 16 million in audience. The song, which interpolates “Somewhere Over the Rainbow” from the iconic 1939 film The Wizard of Oz, is her ninth top 10. It’s from the September deluxe edition of her 2024 album, Whirlwind.
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