Fashion icons may differ in taste, but one trait they all share is originality — the confidence to wear something unexpected and make it entirely their own.
Olivia Palermo pairs her sophisticated ensemble with elegant Chloé Hoya CE604S sunglasses, adding a touch of glamour to her appearance
Our resident style crush, Olivia Palermo, never fails to whip up a curious combination that is characteristically her – eccentric yet polished – even if occasionally, the eccentric factor is cranked up a notch too high.
Adding a touch of sparkle, Olivia Palermo carries a white Chloé Elsie crystal-embellished bag
While we’re still a bit baffled by her thigh-high-suede-and-plaid look, we can’t help but let it slip because this girl is just too gorgeous.
Plus, she has already earned enough cute skirt look points to make us look the other way.
Olivia Palermo in a sheer dot-panel blouse arriving at the Paris Fashion Week Ready-to-Wear Spring/Summer 2014 in Paris on September 29, 2013 (Credit: SIPA / WENN)
Olivia arrived at the Chloé show during Paris Fashion Week and showed her all-out support by dressing herself head-to-toe in Chloé.
👡 Explore Celebs Styling Chloé:
- 📋 How to Tell Real vs Fake Chloé Bags – Features Kate Bosworth carrying the crystal-embellished Chloé Mira shoulder bag at the LA boutique opening, with authenticity tips for fans.
- ✨ Olivia Wilde at 2025 Taormina Festival – She wears pale-yellow Chloe lace platform sandals and a matching lace dress at the photocall, exemplifying the brand’s feminine boho style.
- 🎀 Emma Roberts in Vintage Chloé at PFW – Stuns in a Pre‑Fall 2017 floral suit with nude “Harper” pumps and the Nile bracelet bag, channeling Parisian chic.
- 🌿 Celebs Wearing Chloe “Maxime” Wedges – Highlights Kiernan Shipka, Georgia May Jagger, Sienna Miller, and Kathryn Newton all stepping out in the fringed Maxime wedges at Paris Fashion Week.
Showcasing the luxurious texture, these are Olivia Palermo’s Chloé python knee boots, complete with a practical back zip
The stylist picked an A-line wool skirt in a blue-gray tone, which she paired with an adorable sheer dot-panel blouse.
Olivia Palermo’s Chloe Elsie crystal-embellished cream leather clutch
Olivia incorporated warm earth tones into her ensemble by pairing rich brown boots with her A-line skirt and cinching the look with a coordinating belt. This thoughtful styling choice tied the outfit together.
Olivia Palermo pairs a sheer dot-panel blouse with a blue A-line skirt, cinched by a brown belt, and accessorized with Chloé python knee boots and a crystal-studded bag, demonstrating her signature blend of eccentric and polished style
While the intention behind pairing tall boots with an A-line skirt is seasonally appropriate, the overall effect feels slightly unbalanced. The look might have benefited from a subtle break between the skirt hem and the boots, either with a shorter shaft or a hint of leg to lighten the silhouette visually.
On Olivia’s 5 feet 5 inches (165.1 cm) frame, the heavy python boots dominate the outfit and weigh down what could have been a more fluid, dynamic ensemble. A touch more contrast or proportion play — one of Olivia’s usual strengths — might have elevated this look from bold to beautifully refined.
Still, it’s a creative take on fall textures, and the head-to-toe Chloé styling keeps it cohesive and high fashion.
Chloé High-Waisted Wool A-Line Skirt, $1,210
👠 Explore Olivia Palermo’s Standout Shoe Moments:
- 💥 Olivia Palermo’s Casadei Love Affair at Milan Fashion Week – From over‑the‑knee Superblade boots to sleek pumps, she brings bold luxury footwear to every runway show.
- 🌟 Summer Sparkle: Miu Miu Crystal Mules in Montauk – Olivia topped off her ivy‑print Alice + Olivia dress with glittering crystal‑embellished mules.
- 🖤 Day‑to‑Night in Gianvito Rossi “Augusta” Sandals – She seamlessly transitioned velvet ankle-wrap sandals from runway day to glamorous Milan night.
- 👢 Birthday Stroll in Gianvito Rossi Chester Chelsea Boots – Brooklyn street style warmed up with sleek, lug‑soled Chelsea boots for her 35th birthday outing.
- ⚔️ Edgy Paris: Gianvito Rossi Combat Boots with Culottes – At Paris Fashion Week, she paired knee‑high combat boots with culottes for a powerful, trend-forward look.