Denim skirts are officially back—but with a twist. No longer just a Y2K throwback, the 2025 version is sleeker, sharper, and way more versatile. From midi pencil cuts to slouchy maxis and tailored minis, today’s denim skirts deserve styling that feels modern, not nostalgic in the wrong way.
And the secret to making your denim skirt feel fresh? Your shoes. The right footwear can instantly elevate a denim skirt into fashion-forward territory, while the wrong pair can trap your look in early-2000s limbo (hello, peep-toe wedges and gladiators).
Below, we’ve rounded up five shoes that make denim skirts cool again—and five that are best left in your MySpace-era photo albums.
1. Sleek Kitten-Heel Mules
Minimalism at its finest, kitten-heel mules bring an editorial flair to denim skirts. Think of them as the quiet achievers in the fashion world. Their understated elegance effortlessly elevates your look. Whether you’re attending a casual brunch or a sophisticated evening event, these mules ensure you stand out subtly.
The low heel offers just enough lift to elongate the legs, allowing for a polished appearance without compromising comfort. Originating in the 1950s, kitten heels made a comeback with a modern twist, blending vintage charm with contemporary style.
2. Chunky-but-Sleek Loafers
Embrace the academic-meets-streetwear vibe with chunky loafers. These shoes add a structured edge to denim skirts, making them a must-have for fashion-forward individuals. With or without socks, their versatility is unmatched.
Prada-inspired designs, particularly in glossy leather, enhance both comfort and style. Perfect for those who love a retro yet modern look, these loafers bring a touch of academia to everyday wear. They channel the spirit of intellectual rebellion that defined the 90s, now reimagined for the modern wardrobe.
3. Tall Slim Boots
Tall, slim boots, especially in suede or leather, are the epitome of sophistication. When paired with denim skirts, they create an elongated silhouette that is both flattering and luxurious. Knee-high or over-the-knee styles transform a simple outfit into a striking ensemble.
These boots have a storied past, often associated with powerful fashion statements. Their ability to merge practicality with high style is timeless. From high fashion runways to everyday chic, they seamlessly blend with the changing seasons, making them perennially stylish.
4. Retro Sneakers
Effortless cool defines the retro sneaker trend. With a nod to the past, these sneakers infuse a laid-back vibe into denim skirts. They’re perfect for those who embrace the ‘model-off-duty’ look, adding a sporty touch to any outfit. Brands like Adidas Sambas and Nike Killshots epitomize this style, offering versatility and comfort.
Their resurgence in the fashion scene is a testament to their timeless appeal. When you want to balance style and ease, retro sneakers are the go-to choice, effortlessly bridging the gap between old-school charm and modern flair.
5. Sculptural or Statement Heels
For those who dare to be different, sculptural heels are a bold choice. Denim skirts paired with these heels transition from day to night with ease. The architectural elements, such as geometric shapes and metallic finishes, make them conversation starters.
Perfect for evening soirees or gallery openings, they transform your look instantly. This trend pushes the boundaries of traditional fashion, celebrating individuality and creativity. With origins in avant-garde design, these heels are not just footwear; they’re wearable art. Make a statement without uttering a word.
6. Peep-Toe Wedges
A relic from the 2000s, peep-toe wedges often evoke memories of ‘mall chic.’ Their once-popular style now feels outdated, with their clunky design clashing with today’s streamlined silhouettes. While they once symbolized casual elegance, they no longer align with modern aesthetics.
These shoes often come off as too chunky, detracting from the sleek lines of today’s denim skirts. Their appeal has waned as fashion has moved towards cleaner, more refined designs. Once a staple for casual outings, they’re now best left in the fashion archives.
7. Overly Distressed Cowboy Boots
Cowboy boots, particularly when overly distressed, can feel costume-like unless styled intentionally. While they offer a rugged charm, they often clash with the modernity of today’s denim skirts. Once a symbol of Western fashion, these boots have seen their heyday pass.
Their overly worn aesthetic feels more suited to a themed event than everyday wear. As fashion evolves, these boots stick out as reminders of a bygone era. Unless part of a deliberate high-fashion Western ensemble, they skew out of date in contemporary styling.
8. Flat Ballet Flats
Ballet flats, especially those with bows, often seem too dainty for denim skirts. Their delicate design can appear matronly and dated. Once a go-to for effortless style, they lack the bold impact that modern fashion demands.
While they offer comfort, their appeal diminishes when paired with today’s dynamic skirt cuts. The juxtaposition of their femininity with a denim skirt can feel uninspired. Though they hold a place in fashion history, their relevance has faded, making way for more contemporary alternatives that resonate with today’s trends.
9. Basic Flip-Flops
Flip-flops are synonymous with casual, beach-ready style. However, when paired with denim skirts, they fall short of making a fashion statement. Although they offer unparalleled comfort for leisurely strolls, they lack the sophistication required for a polished look.
These sandals often cheapen an outfit, detracting from the potential elegance of a well-styled denim skirt. Their ubiquitous nature makes them a staple for beach vacations but a misstep for stylish city outings. Reserve them for sandy shores, where their simplicity matches the laid-back atmosphere.
10. Knee-High Gladiator Sandals
Once a festival favorite, knee-high gladiator sandals now seem like a relic of 2010 Coachella fashion. Their intricate straps visually segment the leg, often clashing with modern denim skirt cuts. While they were once heralded for their edgy appeal, their time has passed.
Today’s fashion leans towards simplicity and elegance, making these sandals feel overly complicated. Though they evoke nostalgia for music festivals past, their practicality and style no longer align with current trends. They’re a reminder of an era defined by bohemian exuberance that has since evolved.