FOREVER PLAID

First-time mom Olivia Wilde, who welcomed son Otis Alexander on April 20, grabs breakfast to go in Boston on April 3 in a black tailored coat, plaid button-down, ripped skinny jeans and black booties. The actress didn't quite make it to her May 4 due date despite her adorable trick to remember it.

'STACHE DASH

While walking her dog Paco in New York City on March 21, Wilde stays warm in a fun graphic sweater over a blue patterned shirt paired with DL1961's Kate Maternity Straight jeans and black AllSaints New Jonas boots.

STREET CHIC

It's a cool-girl moment for the actress, in the form of a navy and tan striped coat, cream sweater, black jeans, fedora and booties, in N.Y.C. on March 10.

TWO STEP

Couple crush alert! Wilde keeps it casual in a Kanye West "Yeezus" concert tee, black pants, red fur-lined moccasins and a cross-body bag for a March 8 stroll with Sudeikis in N.Y.C. But just a few days earlier (March 2), she bumps it up in a high-neck black gown paired with a white Jimmy Choo clutch and Lorraine Schwartz jewelry. "We are wearing Valentino," the Her actress told PEOPLE of her Academy Awards ensemble.

#ALMOSTCOOKED

For a Feb. 23 day of shopping with the girls in Venice, Calif., Wilde stays comfy in Ella Moss's cool boho Tuscana silk maxi dress. "Sure I've looked like this after Mexican food but this time it's a BABY. #almostcooked #nineweekstogo #holyfuamp$," she jokingly wrote after posting a pic of her stylish maternity ensemble on Instagram.

GOING GREEN

To complement her gorgeous pregnancy glow, Wilde dons a sequined emerald Gucci gown, Emm Kuo metallic clutch and Forevermark ring at the Jan. 12 Golden Globes in L.A. The mom-to-be told PEOPLE she chose the floor-length, formfitting dress because, "Until about a week ago, I just looked fat. I wanted to be like, 'I'm not fat, I'm pregnant!'"

WILDE THING

Biker babe! The actress opts for Gucci again, but this time she toughens up a black printed LBD with a cropped leather jacket and a metallic green Jimmy Choo Cosma clutch for W's Golden Globes party in L.A. on Jan. 9. The only beauty accessory needed? Her lush locks and fresh face.

HER MOMENT

The first hint that there's a baby boy on the way? Wilde's bright blue dress at the L.A. premiere of Her on Dec. 12. Major fashion accessories (Jacob amp Co.'s micro-pave stud earrings and Jimmy Choo Kahlua pumps) help accentuate the first signs of her growing bump.

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