After captivating us at Kate Winslet’s Hollywood Walk of Fame ceremony and making a fabulous entrance at the Los Angeles premiere of Divergent, Shailene Woodley schooled us on how to work menswear-inspired looks in two different ways at CinemaCon in Las Vegas.
💫 Jump to a Look:
This season’s menswear trend has taken Hollywood by storm, and we’ve seen several celebrities, including Emma Watson, Angelina Jolie, and Scarlett Johansson, successfully incorporate it into their style.
1. Casual Chic: Khaki Dolce & Gabbana Set With Louboutin Brogues
Shailene Woodley effortlessly rocks a menswear-inspired look at CinemaCon, wearing a chic khaki vest and cropped trousers ensemble paired with crisp white Louboutin brogues in Las Vegas, Nevada, on March 27, 2014 (Credit: DJDM / Judy Eddy / WENN)
At this year’s CinemaCon, Shailene stayed true to her laid-back style. She attended a special presentation of 20th Century Fox in a khaki vest and matching cropped trousers from Dolce & Gabbana.
Shailene Woodley keeps it simple and elegant, pairing a sleek khaki vest with a delicate gold pendant for a polished look
2. White Python Louboutins: A Luxe Take on Menswear Footwear
She styled it with a crisp white shirt and a pair of white python brogues from Christian Louboutin—an iconic French designer known for his red-lacquered soles and meticulous craftsmanship.
👞 Explore Stylish Brogue Moments:
- 📘 Oxford Shoes vs. Derby Shoes: Brogues explained — a clear breakdown of brogues and their mid-century Irish/Scottish roots, with photos and styling tips.
- 👢 Gigi Hadid’s Tokyo arrival — she rocked Prada brogue-patterned ankle boots on her airport runway.
- 🎬 Kristen Stewart’s Delphine brogue boots — Dr. Martens’ twist on classic brogues at a Hollywood premiere.
- 💁♀️ Jessica Alba’s white AGL brogues — street-style elegance on Melrose Boulevard.
- 👠 Helena Bonham Carter’s platform brogues — black platforms that balance whimsy and sophistication on the red carpet.
- 🎤 Taylor Swift’s retro brogues — mint pastel skinnies paired with heeled lace-up brogues for a vintage-chic street look.
Louboutin’s men’s brogues, including the luxurious “Fred” style that Shailene wore, blend Parisian elegance with Italian artistry and are often crafted from premium materials such as python, calfskin, and suede.
These fashion-forward shoes elevate menswear-inspired outfits with their sharp silhouette, tonal detailing, and signature flash of red beneath the sole.
Shailene Woodley completes her look with these eye-catching white python brogues from Christian Louboutin
This look wasn’t exactly mind-blowing, but Shailene’s confidence and infectious charm made it work. What do you think?
The 22-year-old actress wore the “Fred” brogues from Christian Louboutin, featuring round toes, tonal grommets, and stunning python leather. While we admire the classic black and white versions, we’re especially fond of the vibrant yellow pair Sienna Miller rocked in London.
Shailene Woodley’s white python Christian Louboutin brogues add a sophisticated, textured flair to her red carpet menswear-inspired ensemble
Later that day, Shailene switched up her style to accept her Female Star of Tomorrow award at the Big Screen Achievement Awards, showcasing an edgier, more polished ensemble.
3. Tailored Elegance: Black Satin Suit & Red Heels for the Win
Shailene Woodley exudes sleek sophistication in a black satin Dolce & Gabbana suit paired with sultry red pumps as she proudly accepts her Female Star of Tomorrow award at CinemaCon in Las Vegas, Nevada, on March 27, 2014 (Credit: DJDM / Judy Eddy / WENN)
She embraced her sensuality in an androgynous yet incredibly sexy look courtesy of Dolce & Gabbana. Shailene wore a black satin suit and flashed a hint of her black lace bra, which added a sultry touch to her ensemble.
Shailene Woodley embraces a sleek look with her cropped hair styled to one side and a pop of color on her lips
Her sleek, cropped hair added an edgy touch to her look, which she completed with pink lips and bold red Dolce & Gabbana pumps.
Shailene Woodley adds a touch of glamour to her look with bold red satin heels, delicately paired with a shimmering anklet for an extra dash of elegance
What do you think of Shailene’s menswear-inspired looks? Which one do you like best?
4. More of Shailene’s Most Memorable Shoe Moments
From barefoot red carpets to bold designer heels, Shailene Woodley has consistently delivered unexpected and unforgettable fashion choices. If you enjoyed her CinemaCon looks, you’ll love these other style highlights:
👠 Explore Shailene Woodley’s Best Shoe & Fashion Moments:
- 📏 Shailene Woodley’s height (5′ 7¾″) and shoe size (US 9) — plus a gallery of her chic heels from brands like Stuart Weitzman, Christian Louboutin, Ferragamo, Pierre Hardy, and more.
- 🎉 Her bold 2015 MTV Awards look — featuring high-cut buckled boots from Isabel Marant and edgy printed ensembles.
- 👣 ‘Divergent’ Berlin premiere barefoot moment — debuted in Proenza Schouler booties but ended the night shoeless on the red carpet.
- ✨ Legs + sequined shorts look — the 22-year-old rocked black evening sandals from Narciso Rodriguez at a gala, and we dissect her style.
- 💃 Divergent LA premiere — highlighted in gold Stuart Weitzman heels paired with an Elie Saab gown.