Willa Holland Test Drives The Season’s Most Important Outerwear Looks

When Willa Holland arrived in Los Angeles for our October fashion shoot, it was a blistering 90 degrees outside. Hardly coat weather, but that didn’t deter the Arrow actress from playing dress-up in the season’s coolest outerwear. With a new chopped haircut and a giant smile on her face, Holland was game for anything—in this case, an arsenal of cosy pieces rich with of-the-moment textures, menswear detailing, and a touch of sport. Take a minute perusing the final looks, and you’ll be ready to try these fall essentials, too.

Photographer: Naj Jamai

Hair: Luke Chamberlain

Makeup: Sage Maitri

Stylist: Sarah Schussheim

Photo:

Naj Jamai

Within moments of meeting Holland, we couldn’t help but notice that the actress could be a long-lost Delevingne sister—blame it on her striking brows and prominent cheekbones. When asked if she ever gets mistaken for Cara, Holland laughed: “You mean, does she ever get mistaken for me?” It turns out the two grew up together in London, and people would often mix them up. Holland’s personality fits the bill, too. The bubbly 23-year-old is infectious, not afraid to crack a silly face in front of the camera or dance to Taylor Swift. 

Credits: Hugo Women’s Jacket ($595, 800.HUGOBOSS) and Trousers ($345, 800.HUGOBOSS).

Photo:

Naj Jamai

That carefree attitude came alive when she was in the day’s first outfit, a Hugo Boss houndstooth suit draped with a leather motorcycle jacket. Not surprising, considering the ensemble was essentially a nod to the actress’ real-life style. Living full-time in Vancouver, where her CW series Arrow films, Holland credits her first group of real girlfriends for shaping her current look. “They opened up my sense of feminist fashion and definitely helped me get into more sophisticated looks,” Holland says. “I wear suit pants with nice Alexander Wang shoes. They took my tomboyish, baggy style and refined it.”

Credits: Veda Punch Jacket ($895); Hugo Women’s Jacket ($595, 800.HUGOBOSS), Trousers ($345, 800.HUGOBOSS), and Autumn Leather Ankle Boots ($445) in Black.

Photo:

Naj Jamai

But perhaps the most notable change for Holland is her hair, a short cut she’s been trying to do for years. “I was always told not to [cut it] because I would thoroughly regret it,” Holland says. “I kind of got mad that everyone was saying that, so I decided I would try to get my show to write it in. I cut my hair literally the day season two ended. I’m obsessed with it, and never growing it back.” 

Credits: Elizabeth and James Carson Striped Coat ($656) in Heather Grey.

Photo:

Naj Jamai

A hair style that only takes 15 seconds—simply plop in some pomade and mess it up a bit—is perfectly at home with the day’s more easygoing looks. An oversized pinstripe coat and cropped trousers can be all business, but when paired with a relaxed graphic tee and playful flats, are easily weekend-ready. 

Credits: Elizabeth and James Carson Striped Coat ($656) in Heather Grey; Enfants Riches Déprimés Le Rosey Shirt ($225); Elizabeth and James Trenton Wide-Leg Cropped Trousers ($325); Aurélie Bidermann Gold Miki Necklace ($1440); Bionda Castana Bella Flats ($570).

Photo:

Naj Jamai

A self-proclaimed baggy jeans and t-shirt girl, Holland not only knows great denim—she showed up wearing the covet-worthy high-waisted vintage Levi’s shown above—but the power of a statement jacket, too. Holland recalled one of her greatest finds, saying, “I actually have this piece that I found in a vintage shop in Portland. It’s all brown wool on the inside and brown suede on the outside. It’s a bomber jacket with this really nice fashionista-like collar to it that kind of just pops up.”

Credits: Band of Outsiders Faux Fur-Trimmed Wool Biker Jacket ($895) in Grey; Levi’s Tailored Western Shirt ($68) in Dark Heritage; Willa's own Levi's jeans.

Photo:

Naj Jamai

It’s Holland’s eye for cool vintage finds that partially influenced her to start a fashion line, George Clothing Co., with her mother Darnell Gregorio-De Palma. “It’s just in the very early stages,” she says. “It’s being mixed inside the womb and yet to be birthed.” While on set, we got to take a peek at the collection, noting standouts like a paisley-print tee with a contrast pocket and a perfectly feminine polka-dot dress. “It’s based loosely on me and my mum’s style,” Holland added. “It came about because in the early ‘80s my mother was asked by Ron Herman to design pieces for his stores.” 

Credits: Coach Leather Jean Jacket ($1595) in Light Blue.

Photo:

Naj Jamai

As for Holland’s own designer obsessions, she was quick to call out Proenza Schouler, and doted over the olive green backpack by the New York design duo that she toted to our studio, a recent purchase she doesn’t plan on parting with anytime soon. “I have this weird thing that if I buy a backpack like that, I have to wait a year before buying another bag,” she says. “The moment I’ve spent that money, a year has to go by. I have to obsess over it for the next 365 days to know that I want it that bad. I will never become used to being that person that spends three grand here, three grand there. Nobody should do that, no matter how much money you have.”  

Credits: Topshop Ultimate MA1 Bomber Jacket ($110) in Khaki; Frame Le Silk Jacket ($298) in Noir; Veda Five Pants ($795) in Black; Jennifer Zeuner Jewellery Mayfair Necklace ($242) in Rose Gold Vermeil; Bionda Castana China Boots ($915).

Photo:

Naj Jamai

Credits: Topshop Ultimate MA1 Bomber Jacket ($110) in Khaki; Frame Le Silk Jacket ($298) in Noir; Veda Five Pants ($795) in Black; Jennifer Zeuner Jewellery Mayfair Necklace ($242) in Rose Gold Vermeil.

Photo:

Naj Jamai

When Holland isn’t hard at work on her fashion line or reading scripts, the beauty can be found catching up on the latest season of Sons of Anarchy and chilling out to Mazzy Star. “I’ve always been kind of stuck in a couple years back,” she says. “I’m in a Mazzy phase, but I love me some Taylor Swift, too. I like ‘22.’ [That song] was my jam, because when I turned 22 that was all I listened to. I feel like when you are at that age, you must listen to that song for a week straight. And then for the rest of that year, any time you are sad, you have to turn on that song.”

Credits: Tommy Hilfiger Hilfiger Collection Jacket ($1190, 212.223.1824); A.P.C. Paris Sweatshirt ($165) in Gris Chine; Rebecca Minkoff Spencer Suede Cargo Pant ($698, similar style); Jennifer Zeuner Jewellery Mayfair Necklace ($242) in Rose Gold Vermeil.

Photo:

Naj Jamai

So what’s next for Holland? The actress is back to work on her hit comic series Arrow, which premieres its third season tonight. With star power in spades, an incredibly chic fashion sense, and designs skills to boot, it’s clear Holland is more than just a pretty face.  

Credits: Tommy Hilfiger Hilfiger Collection Sweater ($490, 212.223.1824).

Which look is your favourite? Sound off below!