Celebrity Parents Ashlee Simpson-Wentz's Fun & Funky Maternity Style The new mom kept her signature style – maxidresses and fedoras – while awaiting the arrival of baby Bronx. By Melissa Liebling-Goldberg By People Staff Published on November 21, 2008 12:00 PM Share Tweet Pin Email Trending Videos 01 of 22 OCTOBER 12 Whittle/Kaminski/Splash News Online Approaching her due date, Ashlee wraps up her baby preparations by hitting the shops on Montana Ave. in Santa Monica with her mom, Tina. She picked up a big bag of gear at Jenny Bec's toy store, as well as a 'Nightmare Before Christmas' print at Every Picture Tells a Story. 02 of 22 OCTOBER 4 Stefan/INF With her due date looming in a few weeks, the mom-to-be stays comfy in a hip mix of hoodie, long skirt, Rails striped scarf and beanie while taking in Wicked in Los Angeles. 03 of 22 SEPTEMBER 7 Kevin Mazur/WireImage The expectant mom goes for flowing – both in frock and in locks! – as she poses on the red carpet at the 25th Annual MTV Video Music Awards in Hollywood. 04 of 22 SEPTEMBER 6 INF The singer relaxes pre-VMAs by shopping for makeup in skinny jeans, a loose striped top and suede boots. 05 of 22 SEPTEMBER 5 Picasso Foto/John Doe/BuzzFoto It's date night for Simpson-Wentz and her husband Pete Wentz (not pictured) as she heads to Koi in West Hollywood in a printed silk dress and towering heels. 06 of 22 AUGUST 23 George Pimentel/WireImage Simpson-Wentz adds punk edge to her all-black outfit with an orange skull-print scarf as she promotes Request at Zellers in Mississauga, Canada. 07 of 22 AUGUST 18 Most Wanted/Flynet Simpson-Wentz flaunts her curves in a clingy Gypsy 05 maxidress and rakish fedora as she lunches at the Ivy in L.A. 08 of 22 AUGUST 1 Chris Polk/FilmMagic The singer goes belly-first while meeting stars like Miley Cyrus at the taping of the MTV show FNMTV. 09 of 22 JULY 28 Fame In a break from her usual edgy garb, the singer is sweet in an embroidered mini and luxe Badgley Mischka bag while heading for Chinese food. 10 of 22 JULY 25 EF/Flynet Got to satisfy those cravings! The happy couple pick up doughnuts and juice for mom-to-be Ashlee, who glows in her black-and-white Indah maxidress. 11 of 22 JULY 24 Cousart-Ramirez-Rios/ JFX The newlyweds head out for dinner, with Ashlee matching her auburn hair to her flowing halter dress. 12 of 22 JULY 23 RS/PR/Flynet Ashlee gets a great bargain while shopping at American Apparel in L.A. in another sweet printed maxidress. 13 of 22 JULY 15 RS/FT/Flynet No maternity wear here – Simpson-Wentz grabs a two-tone Lauren Moffat top and skinny jeans to have lunch with friends. 14 of 22 JULY 7 PR/RS/Flynet Returning to her favorite skinny J Brand jeans, Ashlee heads to lunch with pals with her trusty Chanel bag in tow. 15 of 22 JUNE 28 DAVID/SNAP-PIX Simpson-Wentz goes for a relaxed vibe in her sweeping Rachel Pally skirt and hippie headband as she runs errands in L.A. 16 of 22 JULY 4 LIMELIGHTPICS.US Happy Independence Day! The mom-to-be gets ready to celebrate with friends in a flowing printed maxidress and studded purse. 17 of 22 JULY 2 Fame Grinning ear-to-ear, the singer stays cool in a printed Juicy Couture maxidress and Coach sandals as she grabs pizza for lunch with Pete. 18 of 22 JULY 3 TOM/PR/JP/Flynet Sticking to her headband and maxidress combo, Ashlee keeps comfy in a Gypsy 05 printed jersey dress as she visits friends in L.A. 19 of 22 JUNE 17 Paul Warner/WireImage Not slowing down at all, the star keeps husband Wentz company to open his new bar in Chicago in a slim minidress, oversized chain necklace and towering platforms. 20 of 22 JUNE 10 Cousart-Ramirez-Rios/ JFX Hot mama alert! The star flaunts her new curves in a plunging maroon maxidress while out and about in L.A. 21 of 22 MAY 31 Isaac Brekken/Getty Images Ashlee makes her first red carpet appearance since confirming her pregnancy in a chic sheer black dress and peeptoe booties at the Palms Palace opening in Las Vegas. 22 of 22 MAY 26 AFM/JAK/Finalpixx The week after getting married to Pete Wentz, the striped-clad singer spends a fun Memorial Day with pals – as rumors swirl about her alleged pregnancy.