Nicky Hilton’s Maternity Wardrobe: How Canfora Sandals & Pointed Pumps Transform Pregnancy Style

Nicky Hilton’s maternity wardrobe showed how versatile footwear can transform the same stage of pregnancy into distinctly different looks. Across appearances in Los Angeles and New York in February 2022, she alternated between handcrafted flat sandals for daytime outings and classic pointed-toe pumps for evening events, proving that comfort and polished style can easily coexist.

Below is a closer look at the outfits, accessories, and shoes that defined these appearances.

Nicky Hilton Keeps It Breezy in an Alice + Olivia Floral Maxi Dress and Canfora Gail Flat Sandals

While spending time with her youngest daughter, Teddy, in Los Angeles, Nicky Hilton opted for an easy spring outfit built around comfortable footwear and a flowing designer dress.

She wore Alice + Olivia’s “Alexandria” floral maxi dress, an empire-waist style with a plunging V-neck, shirred panels, front buttons, deep red trim, and playful pom-pom tassels that suited the relaxed daytime outing.

Pregnant Nicky Hilton steps out in Los Angeles with daughter Teddy on February 24, 2022, pairing an Alice + Olivia floral maxi dress with minimalist Canfora Gail flat sandals and a woven raffia tote for an effortlessly polished maternity look (Credit: BauerGriffin / INSTARimages)

The “Alexandria” dress showcases Alice + Olivia’s signature romantic bohemian aesthetic with multicolored floral prints, deep red trim, pom-pom tassels, shirred panels, and a plunging V-neckline. Although not designed specifically as maternity wear, its empire waist and flowing silhouette comfortably accommodate a growing baby bump without sacrificing the dress’s original shape.

She kept the accessories understated, layering two heart pendant necklaces, stud earrings, and a handful of statement rings that complemented the colorful print without overwhelming it.

Nicky Hilton showcases her growing baby bump in an Alice+Olivia Alexandria plunging floral maxi dress (Credit: BauerGriffin / INSTARimages)

She finished the look with loose waves, minimal makeup, Lanvin gradient sunglasses, and a Carolina Santo Domingo raffia tote.

Known for combining architectural silhouettes with natural materials, the woven bag echoed the relaxed feel of the floral maxi dress, while the oversized sunglasses completed the effortless daytime styling.

Nicky Hilton wears her blonde tresses in loose waves and styles her look with Lanvin gradient sunglasses (Credit: BauerGriffin / INSTARimages)

The outfit was finished with Canfora’s handcrafted “Gail” flat sandals. Handmade on the island of Capri by the Italian shoemaker founded in 1946, the minimalist three-strap design reflects the brand’s long association with understated Mediterranean style.

Built with a hand-stitched leather sole, concealed iron arch support, and a non-slip rubber heel, the sandals complemented the airy maxi dress while offering practical comfort for a day spent walking around Los Angeles.

Nicky has also paired flowing floral dresses with natural-textured flat sandals, including Carrie Forbes’ braided raffia “Noura” sandals. While the Canfora pair has a cleaner leather construction, both styles show how lightweight flats can complement a long printed dress without adding visual weight.

Nicky Hilton completes her breezy casual outfit with the minimalist Canfora Gail flat sandals (Credit: BauerGriffin / INSTARimages)

Nicky Hilton Pairs a Little Black Dress With Classic Black Pointed-Toe Pumps for Dinner at Craig’s

A day earlier, Nicky Hilton chose a more structured maternity look for dinner at Craig’s in West Hollywood, pairing a fitted ribbed little black dress with classic black pointed-toe pumps.

Nicky Hilton grabs dinner at Craig’s in a little black dress with a Max Mara Teddy jacket (Credit: BauerGriffin / INSTARimages)

To stay warm, she layered the dress beneath Max Mara’s oversized “Teddy Icon” coat.

Introduced in 2013 and inspired by an archival Max Mara design from the 1980s, the plush alpaca-, wool-, and silk-blend coat has become one of the Italian house’s signature outerwear pieces, its cocoon silhouette contrasting neatly with the fitted ribbed dress underneath.

The same oversized Max Mara coat has also appeared in Blake Lively’s winter wardrobe with Rag Bone “Sloane” boots. Lively used substantial combat-style footwear to continue the coat’s relaxed proportions, while Hilton’s pointed-toe pumps created a sharper contrast with its voluminous shape.

Her coat featured a double-breasted button front closure, a notched lapel collar, and pin-buckled tan leather straps at the hem. Diamond stud earrings and a delicate silver chain necklace added subtle polish without competing with the clean lines of the outfit.

Nicky Hilton adds volume to her wavy blonde hair and glams up with her signature pink makeup look (Credit: BauerGriffin / INSTARimages)

Soft waves and her signature pink-toned makeup complemented the clean, monochrome palette, while Valentino Garavani’s Roman Stud shoulder bag introduced texture through oversized quilted leather and enlarged pyramid studs—a modern reinterpretation of the house’s iconic Rockstud motif.

Classic black suede pointed-toe pumps finished the look, balancing the oversized Teddy coat with a streamlined silhouette.

Nicky Hilton finishes off her night out outfit with classic black suede pumps (Credit: BauerGriffin / INSTARimages)

The pointed-toe pump remains a recurring choice among celebrities for evening wear because its narrow profile works particularly well beneath fitted dresses and substantial outerwear. For a designer-specific variation, see how celebrities have styled Christian Louboutin’s sharply pointed Hot Chick pumps with cocktail dresses, tailored separates, and red-carpet gowns.

Nicky Hilton Styles an Alice + Olivia Leopard Slip Dress With a Leather Jacket at New York Fashion Week

Nicky Hilton also embraced bolder evening dressing while attending the Alice + Olivia cocktail and dinner party during New York Fashion Week.

She chose the label’s “Harmony” leopard-print slip dress, demonstrating how statement prints could still feel refined when paired with classic accessories and understated footwear.

Nicky Hilton attends Alice + Olivia’s cocktail and dinner party during New York Fashion Week on February 12, 2022, pairing a leopard-print slip dress with a cropped leather biker jacket, classic black pointed-toe pumps, and a Valentino Rockstud Box bag (Credit: Janet Mayer / Startraksphoto)

The “Harmony” slip dress featured a softly draped cowl neckline, slender spaghetti straps, an asymmetric hem, and a front slit. Its bias-cut construction allowed the fabric to skim naturally over her growing baby bump, illustrating why the silhouette has remained one of Alice + Olivia’s most enduring evening styles.

A cropped black leather biker jacket added structure to the fluid silhouette, while a Valentino Rockstud Box shoulder bag introduced the brand’s signature pyramid studs.

Nicky Hilton drapes her baby bump in an Alice+Olivia Harmony leopard-print slip dress with a black leather biker jacket (Credit: Janet Mayer / Startraksphoto)

The compact shoulder bag featured both a top handle and a detachable strap, making it practical and distinctive.

Layered chain necklaces, rings, and loose waves completed the look without competing with the leopard-print dress, while classic black pointed-toe pumps kept the outfit grounded and polished.

Nicky Hilton looks beautiful with wavy blonde hair, pink smokey eyeshadow, and pink lipstick (Credit: Janet Mayer / Startraksphoto)

More of Nicky Hilton’s Signature Shoe Style

From minimalist flat sandals for daytime outings to classic pumps and statement designer heels for evening events and fashion week appearances, Nicky Hilton’s wardrobe consistently shows how carefully chosen footwear shapes each look. Explore more of her standout shoe moments below.