Few celebrities can pull off vintage-inspired footwear quite like Alexa Chung. Whether she’s styling fringed loafers, ankle-strap heels, or retro sneakers, she always makes them look effortlessly modern.
And she’s not alone—other A-list stars are also embracing vintage-inspired shoes. Let’s take a closer look at some of the most stylish celebrity moments featuring retro footwear.
Alexa Chung captured leaving a Vogue seminar in London, effortlessly stylish in her daytime outfit, April 27, 2013 (Credit: Will Alexander / WENN)
I guess part of Alexa’s charm is her unaffected quality. She seems unfazed by a bad hair day.
Alexa Chung departs from a Vogue event, showcasing her relaxed, chic style on a London street, dated April 27, 2013
The television presenter and contributing editor at British Vogue doesn’t take herself too seriously, fashion-wise, either, and makes it a point to inject fun in her ensembles.
Style icon Alexa Chung leaves a Vogue seminar, blending vintage flair with modern fashion in London, April 27, 2013
Alexa has been donning rompers and looking great in them when everyone else considers it tacky and juvenile.
In April 2013, Alexa Chung was spotted wearing an adorable gingham dress from Paul Smith’s Black Label, proving that this classic print never goes out of style. Whether you prefer a structured silhouette like Alexa’s or a more relaxed, flowy design, you can explore a curated selection of gingham dresses at Farfetch.
Three stylish gingham midi dresses from Comme Des Garçons, GANNI, and AZEEZA showcase unique silhouettes with ruffled sleeves, classic checkered patterns, and modern jacquard textures, paired with statement footwear
Although the gingham print is massively popular, it has always been a classic and indispensable print. So expect a gingham dress like Alexa’s to still work its wonders years from now.
Alexa styled her dress with a structured blazer, a Chanel crossbody purse, fringed vintage-style shoes (with socks!), and a pair of retro cat-eye sunglasses. The look is vintage-inspired but works well even with a more modern aesthetic.
It seems like Alexa is a fan of Paul Smith because her shoes are also from the design powerhouse.
Alexa Chung attended The Vogue Festival in London wearing a chic Paul Smith Black Label checked dress with a neat collar and pleated skirt, accented by a black leather belt, and completed with buckled shoes and black socks
Alexa Chung isn’t the only fashion-forward star embracing gingham. Many celebrities have turned to this classic print, each putting their own stylish twist on the look.
Stepping Out in Style: Celebrities Who Love Gingham
Let’s explore some standout moments where stars have donned gingham, with a particular focus on their footwear choices:
Vanessa Hudgens in Retro Dolce & Gabbana
- Event: Street-style sighting
- Outfit: Vanessa Hudgens showcased a feminine retro vibe in a tea-length Dolce & Gabbana gingham dress.
- Footwear: She paired this ensemble with black d’Orsay flats, a white leather messenger bag, and oversized sunglasses.
- More Details: Vanessa Hudgens’ gingham dress moment
Pixie Lott’s Peplum Gingham Dress
- Event: Fashion event
- Outfit: British singer Pixie Lott flaunted her curves in a peplum gingham dress featuring a pencil skirt.
- Footwear: She completed the outfit with loafer flatforms, quirky sunglasses, and a blue box bag.
- More Details: Pixie Lott’s modern take on gingham
Daisy Lowe’s Floral and Gingham Fusion
- Event: London Fashion Week
- Outfit: Daisy Lowe turned heads in a form-fitting Dolce & Gabbana dress that combined floral and gingham patterns.
- Footwear: She elevated the look with sky-high pumps and a sleek clutch.
- More Details: Daisy Lowe’s gingham-meets-floral style
Emmy Rossum’s Casual Gingham Shirt Dress
- Event: Day out in Los Angeles
- Outfit: Emmy Rossum mastered casual chic in a gingham shirt dress.
- Footwear: She paired the look with white Paul Andrew pumps and a nostalgic car-shaped bag.
- More Details: Emmy Rossum’s effortlessly stylish gingham look
Victoria Justice’s Sheer Gingham Ensemble
- Event: Red carpet appearance
- Outfit: Victoria Justice embraced a daring look with a sheer gingham dress, cinched at the waist with a belt.
- Footwear: She accessorized with banded BCBGeneration sandals and a vibrant pink clutch.
- More Details: Victoria Justice’s bold gingham fashion choice
Sarah Paulson in Valentino’s Checkered Design
- Event: Award show red carpet
- Outfit: Sarah Paulson graced the red carpet in a black and white checkered Valentino dress.
- Footwear: She paired the look with Nicholas Kirkwood ‘Leda’ heels.
- More Details: Sarah Paulson’s elegant gingham moment
Kate Upton’s Bold Gingham Skirt
- Event: Vogue Festival 2015
- Outfit: Kate Upton took a fashion risk by pairing a Dolce & Gabbana gingham A-line skirt with a floral brocade cardigan.
- Footwear: She completed the look with lace Kurt Geiger pumps.
- More Details: Kate Upton’s mix-and-match gingham look
Blanca Suarez’s Monochromatic Gingham Ensemble
- Event: Fashion week appearance
- Outfit: Spanish actress Blanca Suarez opted for a chic Oscar de la Renta gingham outfit.
- Footwear: While her ensemble was monochromatic, she added a pop of color with her choice of sandals.
- More Details: Blanca Suarez’s elegant gingham look
These celebrities exemplify the versatility of gingham, each incorporating the pattern into their wardrobes with distinctive styles and footwear choices.
As you can see, Alexa’s dress boasts a pointed collar and a midi hem length with a pleated skirt. It comes with a belt to cinch the dress in its waist. You can even put a petticoat underneath the skirt to make it flare and give you a 60’s look.
Detail of Alexa Chung’s Paul Smith Black Label dress, highlighting the elegant checked pattern and sophisticated design, priced at $670.84
Alexa Chung isn’t the only star embracing vintage-inspired footwear. From classic Mary Janes to nostalgic sneakers, other fashion-forward celebrities have also been spotted stepping out in retro-chic shoes.
Stepping Out in Style: Celebrities Who Love Vintage-Inspired Shoes
Let’s take a look at how some of the biggest names in fashion are making vintage footwear a modern staple:
Katie Holmes Revives ’90s Fashion with Autry Sneakers
- Event: Casual Outing in New York City
- Outfit: Katie Holmes was spotted in a taupe sweater paired with a brown flannel jacket featuring a black and white plaid pattern, reminiscent of 1990s grunge fashion.
- Footwear: She completed her look with Autry “Medalist” sneakers, which are vintage-style low sneakers inspired by 1980s tennis shoes.
- More Details: Katie Holmes’ Street Style with Autry Sneakers
Elle Fanning Channels Retro Vibes in Saint Laurent
- Event: London Photocall for “A Complete Unknown”
- Outfit: Elle Fanning donned a brown Saint Laurent suit featuring a boxy blazer and loose-fitting, high-waisted pants, evoking a 1940s androgynous aesthetic.
- Footwear: She paired the ensemble with black squared pointed-toe heels, adding a polished finish to her retro-inspired look.
- More Details: Elle Fanning’s Vintage-Inspired Saint Laurent Ensemble
Hunter Schafer’s Ethereal Elegance in Vintage Gaultier
- Event: 22nd Diner De La Mode
- Outfit: Hunter Schafer stunned in a vintage Jean Paul Gaultier ensemble, featuring a creamy blouson and silk skirt.
- Footwear: She complemented the look with yellow Christian Louboutin ballet pumps, adding a pop of color to her ethereal attire.
- More Details: Hunter Schafer’s Vintage Gaultier Ensemble with Louboutin Ballet Pumps
Anya Taylor-Joy’s Retro-Contemporary Look in Celine
- Event: Appearance at NBC Studios
- Outfit: Anya Taylor-Joy opted for a retro-contemporary head-to-toe Celine ensemble, including a cropped jacket and mini-skirt with a 1950s-style houndstooth pattern.
- Footwear: She completed the look with knee-high boots, blending modern and vintage elements seamlessly.
- More Details: Anya Taylor-Joy’s Retro-Inspired Celine Ensemble
Katie Holmes’ Preppy Chic with Gold Mary Jane Flats
- Event: Stroll in New York City
- Outfit: Katie Holmes embraced a preppy look with a gray beanie, oversized ombre sunglasses, and a black Mansur Gavriel tote bag.
- Footwear: She added a festive flair with gold velvet Mary Jane flats paired with matching Lurex socks, giving the ensemble an edgy yet sophisticated touch.
- More Details: Katie Holmes’ Gold Mary Jane Flats and Preppy Style
From Alexa Chung’s fringed loafers to Katie Holmes’ Mary Jane flats, it’s clear that vintage-inspired footwear remains a timeless trend. Whether you prefer a retro sneaker or a classic pump, these styles prove that a touch of nostalgia can elevate any modern look. Which vintage-inspired shoe trend is your favorite?