Emily Ratajkowski’s Chic NYC Street Style: Oversized Leather, Cowboy Boots, and the Buzz Around Pete Davidson

Supermodel and entrepreneur Emily Ratajkowski, celebrated for her distinctive fashion sense and captivating presence, recently turned heads during a casual yet stylish outing in New York City. The 31-year-old fashion icon was spotted enjoying the crisp autumn weather with her one-year-old son, Sylvester, showcasing an effortlessly cool ensemble that blended high fashion with everyday comfort. Her choice of an oversized leather jacket and classic cowboy boots immediately caught the attention of onlookers and fashion enthusiasts alike, reaffirming her status as a street style maven.

The outing, which took place on a pleasant Friday in the bustling heart of NYC, saw Ratajkowski confidently pushing her son’s stroller. Her chosen attire was a vibrant teal and white oversized leather jacket, layered over a simple black top and black jeans, creating a striking contrast that was both bold and chic. Complementing this statement piece were light blue cowboy boots, adding an unexpected yet perfectly balanced touch of Americana to her urban look. A blue baseball cap, worn casually with some strands of her hair artfully framing her face, completed the ensemble, epitomizing a blend of laid-back cool and deliberate style. This public appearance comes amidst a flurry of media speculation surrounding her personal life, particularly reports of her reportedly going on “a few” dates with comedian Pete Davidson, adding another layer of intrigue to her public persona.

As she navigated the vibrant streets of the Big Apple, Ratajkowski exuded an air of serene confidence. Accessorizing her look with sleek sunglasses, she was also seen carrying what appeared to be a coffee cup, a quintessential New Yorker accessory. Her attention was divided between her surroundings, occasionally glancing at the camera, and doting on her son. At one point, she gracefully bent down to adjust the top of the stroller, a tender moment that underscored her dedicated role as a mother. Despite the public attention, she appeared calm and relaxed, fully immersed in the moment with Sylvester. The picturesque autumn leaves scattered on the ground added to the charming ambiance of her stroll, highlighting the quintessential New York fall experience. Ever the attentive parent, Emily was also seen carrying her son’s adorable orange coat when he wasn’t wearing it, a small detail that speaks volumes about her maternal care.

Emily Ratajkowski’s Signature Street Style: A Fusion of Trends

Emily Ratajkowski has long been recognized as a trailblazer in street style, consistently setting trends and influencing fashion conversations. Her recent New York City ensemble perfectly exemplifies her unique approach to dressing – a harmonious blend of high-end pieces, vintage-inspired elements, and accessible fashion. The oversized leather jacket, a staple in many fashion-forward wardrobes, takes on a new life with its striking teal and white colorway. This isn’t just a utilitarian outerwear piece; it’s a bold statement that commands attention while offering a comfortable, relaxed silhouette. Oversized jackets have been a recurring theme on runways and celebrity street style circuits, often signaling a relaxed yet deliberate aesthetic that Ratajkowski masters effortlessly.

The choice of light blue cowboy boots is particularly noteworthy. Cowboy boots have experienced a significant resurgence in recent years, moving beyond their traditional Western roots to become a versatile fashion item. Emily’s decision to pair them with an urban leather jacket and jeans showcases her ability to seamlessly integrate diverse stylistic elements. These boots add an unexpected pop of color and texture, injecting a playful yet sophisticated touch into her overall look. It’s a testament to her fashion acumen that she can make such a distinct item feel utterly natural within a city landscape. Her blue baseball cap further reinforces this blend of casual cool, offering a subtle nod to athleisure while maintaining an air of understated celebrity glamor.

Her style often speaks to a generation that values authenticity and comfort without sacrificing flair. By choosing pieces that are both on-trend and deeply personal, Emily Ratajkowski continues to solidify her position not just as a model, but as a genuine fashion icon. Her ability to elevate simple pieces and mix them with unexpected items provides endless inspiration for her millions of followers, demonstrating that true style lies in confidence and creative expression rather than strict adherence to fashion rules.

Balancing Motherhood and Public Life: Emily’s Journey Post-Divorce

Beyond her impeccable fashion choices, Emily Ratajkowski’s public outings often draw attention due to her intriguing personal life. She shares her adorable son, Sylvester Apollo Bear, with her ex-husband Sebastian Bear-McClard. The couple tied the knot in 2018 in a surprise courthouse ceremony, but their marriage came to an end with Emily filing for divorce in September 2022. Since their split, Emily has been remarkably protective of Sylvester, consciously striving to keep him out of the relentless media spotlight. This commitment to her son’s privacy reflects her dedication to providing him with as normal an upbringing as possible amidst her high-profile career.

Similarly, Ratajkowski has maintained a discreet stance regarding her love life following her separation from Bear-McClard. However, recent weeks have seen a surge in rumors linking her to comedian and actor Pete Davidson, who himself recently concluded a highly publicized relationship with Kim Kardashian. According to an exclusive source close to the situation, Emily and Pete’s acquaintance began on the set of the film, Bodies, Bodies, Bodies. Intriguingly, Sebastian Bear-McClard served as an executive producer on the project, meaning Emily’s visits to the set were not uncommon when she was still married. This initial connection appears to have evolved, leading to their recent dates.

The same source, speaking exclusively to HollywoodLife, elaborated on the initial dynamic between the trio: “Pete and Emily first met when Sebastian and Pete were working on ‘Bodies’ together. It was not strange to see Emily visit Sebastian on set.” The source further painted a picture of Davidson’s charismatic personality, stating, “Pete would make everyone in the film and behind the scenes laugh and it became very familial.” This convivial atmosphere likely laid the groundwork for a friendship that has now blossomed into something more. Davidson is known for his ability to connect with people and his charming demeanor, attributes that seem to have resonated with Emily.

A second insider provided further insight into the burgeoning romance, emphasizing its nascent stage. “Emily’s gone out with Pete a few times, it’s still very new at this point and she’s having fun and not putting any expectations or labels on it,” the insider exclusively shared. This perspective highlights Emily’s desire to navigate her post-divorce life cautiously and enjoy new experiences without the immediate pressure of a committed relationship. “She really wants to stay single for a while and not jump back into a relationship,” the insider added, reiterating her focus on self-discovery and maternal duties. However, the source also acknowledged Davidson’s reputation for forming deep connections: “Of course, Pete’s extremely charming, and he’s very much the relationship type, so it won’t shock anyone if he ends up making her his girlfriend.”

The news of Emily’s split from Sebastian in mid-2022 came as a surprise to many, though reports soon clarified the circumstances. A source close to the situation confirmed to People that the decision to end the four-year marriage was Emily’s. At the time, the source stated, “They split recently. It was Em’s decision. She is doing okay. She is strong and focused on her son. She loves being a mom.” This affirmation underscores her resilience and unwavering dedication to Sylvester, positioning her as a strong, independent woman navigating a new chapter of her life with grace and determination. Her recent public appearances, including this stylish NYC stroll, suggest a woman who is embracing her journey, both personal and professional, with a renewed sense of purpose and self-assurance.