Olivia Palermo’s Brooklyn Street Style: 3 Ways to Style Transitional Footwear

On April 9, 2021, Olivia Palermo, who stands 5’5″ (165.1 cm) and wears a US size 7 shoe, stepped out in Brooklyn with her Maltese, Mr. Butler, in a layered look that captured the transition from winter footwear to spring dressing.

She paired a gray knee-length ribbed turtleneck dress with a navy Brunello Cucinelli zip-front cardigan trimmed with gold embroidery. The softer knit layers were grounded by Gianvito Rossi’s knee-high “Martis” combat boots, one of several substantial lug-soled styles that became recurring fixtures in Palermo’s street-style wardrobe.

Olivia Palermo layers a Brunello Cucinelli cardigan over a gray ribbed dress with Gianvito Rossi Martis combat boots while walking Mr. Butler in Brooklyn on April 9, 2021 (Credit: Instar / WENN)

The cardigan’s oversized shape and textured embroidery added dimension to the neutral dress, while the long ribbed skirt fell just above the shafts of her boots.

The combination is a useful example of how Palermo balanced a softer knit silhouette with heavier footwear rather than switching immediately to lightweight spring shoes.

The ribbed midi dress meets the tops of Palermo’s knee-high boots, creating a continuous column beneath the oversized cardigan

Cradling Mr. Butler, Palermo accessorized with a statement bracelet and a Piaget Limelight Gala rose-gold and diamond watch. She finished the look with smoky eye makeup, loose waves, and the black face mask seen in the photographs.

Palermo wears her hair loose with smoky eye makeup and a Piaget watch while carrying Mr. Butler

Olivia Palermo Grounds a Knit Dress With Gianvito Rossi Martis Combat Boots

The footwear supplied the strongest contrast. Palermo wore the tall version of Gianvito Rossi’s “Martis,” a design she returned to repeatedly in New York and later styled in other settings. Her other Gianvito Rossi Martis looks show how she used the same rugged boot family with denim, coats, and tailored layers.

Made in Italy, the black leather boots combine a lace-up front and round toe with elasticized ribbed panels through the tall shaft. A chunky rubber lug sole and low block heel give the otherwise streamlined knee-high silhouette its utilitarian weight.

Gianvito Rossi’s Martis boots are distinguished by their tall ribbed shafts, front lacing, smooth leather uppers, and chunky lug soles

For more background on the military-derived silhouette and how it moved into mainstream fashion, see our guide to the history and enduring appeal of combat boots.

The Gianvito Rossi Martis combines a fitted ribbed shaft with traditional combat-boot lacing and a substantial rubber outsole

Smythe Tailoring Meets Santoni Double-Monk Loafers

Five days earlier, on April 4, 2021, Palermo took a more tailored approach to transitional dressing while running errands in Brooklyn.

She wore Smythe’s “Birkin” double-breasted coat over a beige ribbed turtleneck and gray skinny jeans with frayed hems, then grounded the look with reddish-brown Santoni loafers.

Palermo pairs Smythe’s military-inspired Birkin coat with cropped gray jeans and chunky Santoni loafers in Brooklyn on April 4, 2021

The Smythe coat uses traditional military references without reading like a costume: a double-breasted front, brass-toned buttons, epaulets, notched lapels, flap pockets, and belted cuffs. Its longer line contrasts with the slim, cropped jeans beneath it.

Oversized tortoiseshell sunglasses and a neat bun keep the focus on the structured Smythe coat

Her shoes brought warmth and visual weight to the otherwise cool-toned outfit. The two-tone Santoni loafers feature almond-shaped toes, double-buckle monk straps, polished leather uppers, and thick lugged rubber soles.

They were not a one-off choice. Palermo returned to the same distinctive silhouette with other 2021 outfits, and our look at her Santoni loafers and Alberta Ferretti mules shows how the chunky double-monk pair became part of her regular flats rotation.

Red nail polish and a maroon phone case echoed the reddish-brown leather without making the accessories feel overly coordinated.

Palermo’s Santoni loafers combine polished reddish-brown leather, double monk straps, and heavy black lug soles

The shoes sit between traditional menswear-inspired monk straps and the exaggerated sole proportions associated with modern chunky loafers.

Our guide to the seven essential loafer styles explains how penny, tassel, bit, platform, and other loafer variations differ, while the Santoni pair shows how those classic dress-shoe cues can be reworked with a tougher sole.

Petal-Pink Smythe Coat With Crystal Slingback Flats

For another Brooklyn outing on March 30, 2021, Palermo moved away from the neutral palette, wearing a petal-pink Smythe coat over a rust-orange shirt and wide-leg black leather trousers.

Palermo combines a petal-pink Smythe coat with a rust shirt, cropped wide-leg leather trousers, and crystal-embellished slingback flats in Brooklyn on March 30, 2021

The single-button coat has a clean, elongated silhouette and finishes with bow details at the sides. Against the rust shirt and black leather trousers, the pink reads as the dominant color without requiring much additional jewelry.

She kept the accessories restrained with oversized tortoiseshell sunglasses, a gold-tone watch with a maroon leather strap, and the white face mask visible in the photographs.

Palermo keeps the accessories simple while carrying Mr. Butler, allowing the pink Smythe coat to remain the focal point

At ground level, Palermo appears to have chosen the Ghazal Paris “Lee” black slingback mules, a pointed-toe style finished with slim crystal-embellished straps across the foot. The low block heels and open backs gave the wide-leg leather trousers a lighter finish than the chunky boots and loafers she wore with her other transitional looks.

Founded in 2019 by Houda Gianasso, Ghazal Paris built its footwear around Italian craftsmanship and classic silhouettes sharpened with details such as crystals and sculptural straps. The label later expanded into jewelry, though it no longer appears to maintain an active retail website.

Palermo’s black slingbacks feature pointed toes, low block heels, slender back straps, and crystal-covered bands across the foot

For a broader look at why loafers, ballet flats, slingbacks, and other low-heeled silhouettes work so well in a varied shoe wardrobe, our guide to essential women’s shoe styles breaks down the key categories and their defining features.

How Olivia Palermo Uses Shoes to Shift Between Seasons

Across the three Brooklyn looks, Palermo relied on footwear to change the character of otherwise practical transitional layers. The Gianvito Rossi Martis boots added a rugged counterpoint to a soft knit dress; the Santoni double-monk loafers gave tailored outerwear a chunkier, menswear-inspired base; and the crystal slingbacks lightened the proportions of wide-leg leather trousers.

That range also fits her broader footwear archive. From lug-soled boots and loafers to pumps, mules, and embellished flats, Palermo tends to use the shoe as a deliberate counterpoint to the clothing rather than simply matching it. YNS’s roundup of Olivia Palermo’s winter designer shoes shows the same approach across several cold-weather outfits.

More Olivia Palermo Shoe Moments Worth Revisiting

Palermo’s shoe wardrobe has ranged from embellished flats and everyday ballet shoes to sculptural pumps and statement boots. These looks show how she has returned to distinctive footwear across red carpets, fashion weeks, and off-duty outings.