6 Shoe Choices To Wear With Skinny Pants In 2025 That Won't Look Outdated

We didn't expect skinny jeans to be among the denim trends dominating 2025, but the 2010s fashion staple has proven that a tight-fitting comeback is imminent. Like any other silhouette, form-fitting pants have experienced their highs and lows throughout the past few decades, with the 2020s seeing a major shift toward looser styles. Skinny jeans experienced a surge in popularity in the early 2000s, being colorfully worn in emo and alternative subcultures. At the same time, trendsetting girlypops and models like Paris Hilton and Kate Moss sported notably low-rise variations in pap shots and on the red carpet. 

Still, skinny jeans are most often associated with the 2010s, staging a major takeover alongside the proliferation of athleisure and the rise of jeggings. It-girls like Kim Kardashian and Beyonce paired skinny jeans with sky-high stilettos or wedges, while hipster icons like Alexa Chung opted for ballet flats and distressed boots. As celebrities and fashion influencers signal the resurgence of the silhouette, fashionistas can avoid looking like they stepped out of the 2010s by styling skinny jeans so they don't look outdated. Specifically, plenty of shoe choices can keep your slim-fit denim firmly in the present, and ready for the future.

Loafers are a classic shoe style that promises to infuse any outfit with a chic sense of affluence or academia, making them the perfect footwear pick to bring skinny-fit pants into the modern era. Amanda Seyfried demonstrated how well the combo can look in a paparazzi shot from December 2024, wearing a puffer jacket, dark bottoms, and a pair of loafer-style pumps from Bottega Veneta. The leather look and gold detailing on the shoes helped elevate an otherwise simple look.

There are few combos as timeless as tennis shoes and denim, so don't be afraid to pair your favorite set of sneakers with skinny jeans like TikTok user Lauren Wolfe. Plus, you can put your best foot forward with 2025 shoe trends and style your sneakers and skinny jeans with a modern flair. Eco-friendly shoes are especially trendy, so if you're not into classics like Converse or Adidas, check out brands like Cariuma and VEJA to get your skinny-jean fix.

Ankle boots are a great footwear option for fashion enthusiasts looking for something with lots of versatility. We're particular fans of the retro vibes Suki Waterhouse channeled with brown, corduroy pants, a fur-lined coat tied at the waist, and heeled boots from Chloe. The entire ensemble demonstrates how you can avoid outdated shoe styles that are aging you by forgoing chunky shapes in favor of an ankle boot that is equal parts sleek and cool.

If ankle-height shoes aren't suiting your mood, tall boots are another great footwear option to pair with skinny-fit pants. The height of the calf-hugging shoes complements the silhouette of form-fitting bottoms, helping to provide nostalgic staples like skinny jeans with a sleek feel. As demonstrated by fashion influencer Aïda Badji, the combo can work particularly well with the aloof chicness of the French girl style, or the moodiness of the dark academia aesthetic, but tall boots are another super versatile footwear option overall.

British family enthusiasts know that one denim trend Kate Middleton cosigns is skinny jeans, with the Princess of Wales providing plenty of styling inspiration. Back in April 2025, the royal demonstrated how to balance practicality with an outdoorsy-infused bookishness, wearing brown, lace-up boots from Chloe with matching, skinny-fit trousers, and an olive-toned blazer. The entire ensemble maintains a hint of 2010s nostalgia while still managing to look stylish and adventure-ready.

Mary Janes round out our list of footwear that's skinny pants-compatible, with the classic style experiencing its own resurgence in popularity. Flat Mary Janes, which have been super trendy, pair particularly well with figure-hugging bottoms, reminiscent of the once-popular ballet flat, while not looking outdated. Fashion influencer Stina Diane put her sporty spin on the combo, styling a pair of double-strapped Mary Janes with slightly distressed denim, a roomy blazer, and a baseball cap. While skinny-fit pants were once thought to be an outdated silhouette, there are plenty of footwear options that bring the bottoms firmly into the modern day.