Ashlee Simpson-Wentz's Fun & Funky Maternity Style

01 of 22

OCTOBER 12

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

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

ASHLEE SIMPSON-WENTZ — 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

The singer relaxes pre-VMAs by shopping for makeup in skinny jeans, a loose

striped top and suede boots.

05 of 22

SEPTEMBER 5

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

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

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

The singer goes belly-first while meeting stars like Miley Cyrus at the taping of the MTV show FNMTV.

09 of 22

JULY 28

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

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

The newlyweds head out for dinner, with Ashlee matching her auburn hair to her flowing halter dress.

12 of 22

JULY 23

Ashlee gets a great bargain while shopping at American Apparel in L.A. in another sweet printed maxidress.

13 of 22

JULY 15

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

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

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

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

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

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

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

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

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

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.