July 23, 2026•5 min read•from Latest from Who What Wear

Not Flip-Flops, Not Flats—It Girls in NYC Are Wearing Summer's #1 Dress Trend With the Boots That Come Back Every Fall

Our take

New York’s style set is demonstrating a keen eye for seasonal transitions. Forget fleeting trends—this summer, the "it" girls are embracing a singular dress silhouette: the slip dress. But with a distinctly forward-thinking twist, they're pairing it with the boots that consistently return each fall. It’s a confident, intentional layering choice that signals a refined understanding of style. For further vacation-ready inspiration, see "Selena Gomez's Italian Getaway Called for the Perfect Little White Dress."

Not Flip-Flops, Not Flats—It Girls in NYC Are Wearing Summer's #1 Dress Trend With the Boots That Come Back Every Fall

## Our Take: The Enduring Allure of Transitional Style and the Dress-Boot Paradox

The fashion landscape, particularly in style capitals like New York City, is perpetually in motion, but the current conversation swirling around the pairing of summer dresses with fall boots speaks to a deeper trend: the deliberate embrace of transitional style. It's a savvy move, signaling a rejection of rigid seasonal boundaries and a celebration of personal expression that transcends fleeting trends. Seeing figures like Dua Lipa champion this look—a seemingly paradoxical combination of breezy summer silhouettes and the grounded weight of autumnal boots—validates what many discerning women have intuitively understood for some time: style isn't about adhering to a calendar, but about layering intention and confidence. This isn’t a new phenomenon, of course; earlier this summer, Selena Gomez demonstrated the effortless elegance of a little white dress on her Italian getaway [Selena Gomez's Italian Getaway Called for the Perfect Little White Dress], proving that a classic piece can be adapted to numerous settings. The key here is the thoughtful curation of contrasting elements – lightness versus structure, warmth versus coolness – to create a visually compelling and unexpectedly harmonious whole.

What’s particularly interesting is the shift in perspective this represents. We've moved beyond the relentless pursuit of *the* trend and towards a more nuanced understanding of personal style as a curated collection of pieces that can be reimagined and recombined throughout the year. The "it girls" of NYC aren't simply following a directive; they're crafting narratives, weaving together disparate elements to tell a story about their individual aesthetic. This resonates with a broader cultural desire for authenticity and self-expression, a move away from the performative aspects of fashion and towards a more intimate and considered approach. The article’s mention of boots that “come back every fall” underscores this point – certain pieces transcend fleeting trends and become enduring staples, capable of anchoring an entire look. Even someone unsure of their fashion sense can find inspiration in this approach [I am new to this type of clothing], demonstrating the accessibility of elevated style when it prioritizes intentionality over fleeting novelty.

This trend also reflects a savvy understanding of consumer behavior. The fashion industry has long encouraged the rapid turnover of wardrobes, fueled by seasonal collections and the relentless pressure to stay "on-trend." However, a growing number of consumers are seeking more sustainable and versatile pieces that can be worn across multiple seasons. The dress-boot combination epitomizes this desire—it’s a practical solution for bridging the gap between summer and fall, minimizing the need for constant consumption. It’s a quiet rebellion against the fast-fashion cycle, an embrace of longevity and adaptability. This aligns with a broader movement towards conscious consumerism, where quality and versatility are valued over quantity and disposability. The confidence with which these "it girls" are styling these ensembles suggests a broader shift toward valuing personal style over fleeting trends, and a willingness to experiment with unexpected pairings to create something truly unique.

Ultimately, the enduring appeal of the dress-and-boots pairing isn’t just about aesthetics; it's about a mindset. It’s about embracing the in-between, finding beauty in the unexpected, and asserting your personal style regardless of the calendar. As we move further into a world that values individuality and mindful consumption, this trend serves as a compelling example of how fashion can be both stylish and sustainable. The question now is: will this embrace of transitional dressing extend beyond dresses and boots, prompting a broader re-evaluation of how we approach our wardrobes and the seasons themselves, or will it remain a stylish anomaly within a system still driven by seasonal cycles?

While it's easy to assume that there's a line between your summer and fall wardrobes, the best dressed people know that the two can happily coexist for those in-between months of August and September—provided you know how to style the pieces together. Today, we're getting a master class in transitional dressing by none other Dua Lipa, whose most recent outfit consisting of a polka-dot halter dress from Réalisation and black knee-high boots is a great example of how chic people will be getting dressed next month.

Lipa was spotted heading into NYC's famed Electric Lady Studios for the zillionth time this week, prompting fans to speculate about a fourth studio album in the making. While most of us would think to pair a pretty polka-dot dress with ballet flats or flip-flops, the pop star's simple shoe swap is actually kind of genius because it can extend the shelf life of all your prettiest dresses into the fall. She opted for a classic pair of black leather knee-high boots, a style that keeps returning year after year.

Ahead, see how Dua Lipa styled the season's biggest dress trend with boots and shop polka-dot dresses and knee-high boots to replicate her summer-to-fall look.