Hilary Duff’s Confident Style Journey: From Women’s Health Cover Boldness to Jimmy Choo × Mugler Glamour

From empowering magazine covers to off-duty denim and red-carpet glamour, Hilary Duff’s style evolution tells a story of confidence, comfort, and California chic.

Below, we revisit some of her most memorable fashion moments — each reflecting her growth as both an actress and a modern style icon.

When Women’s Health unveiled its May/June 2022 issue featuring Hilary Duff posing nude, the shoot became an instant cultural moment — not just for its boldness, but for the confidence it celebrated.

Women’s Health Cover: Hilary Duff Celebrates Body Confidence

Looking back, Duff’s decision to strip down was about self-acceptance and strength, not shock value. Then 34, the actress and mom of three shared on Instagram that she felt “strong and beautiful” during the all-female shoot — laughing her way through poses without her usual high-waisted mom jeans and oversized layers.

Hilary Duff exudes confidence and self-acceptance as she poses nude for the Women’s Health May/June 2022 Body Issue, celebrating strength, growth, and body positivity (Credit: Women’s Health)

The accompanying interview explored her long, public journey with body image — from battling an eating disorder as a teen to learning to appreciate how her body evolved through motherhood. Today, that message feels timeless: a reminder that confidence and style often grow in tandem.

Duff’s approach to fashion has mirrored that transformation. Whether she’s in laid-back Converse sneakers on an L.A. coffee run or stepping out in sky-high Jimmy Choos, she continues to balance comfort, glamour, and self-assured ease — proving that style confidence, like self-confidence, only deepens with time.

Effortless in Los Angeles: Casual Chic with Converse and Bottega Veneta

Spotted in Los Angeles on April 22, 2022, she embraced relaxed tailoring and practical comfort—swapping heels for her favorite black Converse All Star Hi Tops and pairing them with tan trousers, a fitted black tank, and a woven Bottega Veneta Jodie bag that elevated the laid-back vibe.

Hilary Duff wears black Converse All Star Hi Top sneakers with oversized brown pants, a Bottega Veneta Jodie bag, and a Sacai Ma1 Melton jacket in Los Angeles on April 22, 2022 (Credit: MEGA / WENN)

Hilary Duff brought her signature mix of confidence and charm to her role as Sophie in Hulu’s How I Met Your Father, the modern spin-off of How I Met Your Mother.

Set in New York City, the series followed Sophie’s search for love and identity—a storyline that mirrored Duff’s polished yet playful fashion evolution, often blending retro denim, sleek trenches, and statement heels that reflected her effortless approach to modern femininity.

Channeling New-York Cool: “How I Met Your Father” Finale Look

On March 10, 2022, she attended the Hulu-hosted season 1 finale of How I Met Your Father in Los Angeles.

Hilary Duff in a Christopher Esber snap-front lycra shirt paired with a Stand Studio Malou faux leather trench coat and Re/Done 70s cropped faded high-rise straight-leg jeans at the “How I Met Your Father” fan experience in Los Angeles on March 10, 2022 (Credit: WENN / MEGA)

She rocked Jimmy Choo x Mugler mesh-paneled sock boots with a Christopher Esber snap-front lycra shirt, RE/DONE 70s Stovepipe faded high-rise straight-leg jeans, a Stand Studio Malou faux leather trench coat, a Rodo Venere clutch, and Misho textured hoops earrings.

Hilary Duff pairs her jeans with Jimmy Choo Mugler mesh-paneled sock boots (Credit: MEGA / WENN)

Inside the Jimmy Choo × Mugler Collaboration: Architectural Glamour Meets Celebrity Edge

The Jimmy Choo x Mugler capsule collection, launched in 2022, is a masterclass in high-octane sensuality, perfectly fusing the iconic, sculptural glamour of both houses.

Co-designed by Jimmy Choo’s Sandra Choi and Mugler’s Casey Cadwallader, the footwear draws direct inspiration from Mugler’s famed body-conscious designs—like the “Spiral” and “Illusion” bodysuits—translated into sheer sock boots, dramatic over-the-knee silhouettes, and sharply pointed pumps.

Jimmy Choo × Mugler: Iconic Shoe-Fashion Pairings

From sculptural runway boots to daring red-carpet heels, the Jimmy Choo × Mugler collaboration has redefined modern glamour — fusing architectural design with star-powered style moments that continue to inspire.

The collection champions a confident, powerful femininity through architectural heels, graphic mesh panelling that frames the foot, and daring gold chain detailing, making the shoes feel like an extension of the body and a bold statement for the modern, glamorous woman.

Vibrant sock boots from Jimmy Choo x Mugler featuring pointed toes and black fabric uppers with semi-sheer mesh inserts

Before her Women’s Health cover and How I Met Your Father era, Hilary Duff was already shaping her signature mix of California polish and laid-back glamour. Nearly a decade earlier, she was often spotted running errands in chic yet approachable looks that reflected her evolving style confidence.

Classic Hilary: The 2013 Floral Errand Look That Defined Her Early Style Confidence

In late November 2013, the former Lizzie McGuire star was photographed leaving her home to buy flowers — possibly gearing up for Thanksgiving — proving that even her casual moments carried a hint of sophistication.

Hilary Duff exudes effortless polish while picking up flowers in Los Angeles on November 28, 2013, wearing a dark green sweater, sleek leather leggings, and sky-high black-and-white cap-toe pumps (Credit: WENN)

What stood out was how effortlessly polished Hilary looked for such a simple outing. She styled a dark green patterned Equipment Shane sweater with leather-paneled Paige Paloma leggings, finishing the look with striking black-and-white cap-toe pumps that added instant height and sophistication.

The combination was sleek, modern, and unmistakably Hilary — a blend of comfort and quiet glamour.

A closer look at Hilary Duff’s black-and-white cap-toe pumps — a sleek, sky-high pair that added instant sophistication and edge to her casual leather-legging ensemble (Credit: WENN)

Hilary is often spotted in relaxed, casual looks anchored by sneakers or ankle boots, so seeing her step out in towering stilettos offered a refreshing glimpse of her more polished, red-carpet side.

Hilary’s beautiful shoes are Jimmy Choo’s popular “Limit” pumps. The heels on these pumps are towering at 5 inches. That basically means you’ll be teetering in them, especially if you’re not used to wearing heels.

Jimmy Choo “Limit” Tri-Tone Cap-Toe Pumps, $795

Hilary Duff’s Timeless Shoe & Style Highlights

From red-carpet glam to everyday comfort, Hilary Duff’s footwear choices have long reflected her blend of confidence, practicality, and effortless California chic. Here’s a curated look at some of her most memorable shoe moments featured on Your Next Shoes: