How to Wear ’90s Straight-Leg Jeans With Flats in 2025
Despite the popularity of baggy and barrel-leg designs, ’90s-inspired straight-leg jeans continue to be a favorite. The proof? The collection and pictures of the best dressed of the season. With them you don’t need much to stand out, because their charm lies in their almost perfect fit. Not as tight as skinny jeans, not as baggy as baggies, their cut finds the balance between relaxed and sophisticated. The uniform of supermodels and actresses of the decade—the jean silhouette remains as relevant and stylish to this day.
They were a staple in the spring/summer 2025 collections as well, seen at Coach, The Row, Bally and Diesel, to name a few. They’re a great pick for daytime—and the best part is they adapt to any kind of personal style, from minimalist to sporty to preppy. And while we know straight-leg jeans look good with all kinds of footwear, for spring we’re loving them most styled with flat shoes for a naturally elegant look.
If there’s one thing we’ve learned from ’90s icons like Julia Roberts and Kate Moss, it’s that straight jeans are the best choice for solving the morning “what to wear” question in the best way possible. It doesn’t matter if you’re heading to the airport or planning a stroll in the city, they suit every type of occasion and, of course, shoe choice. They look sophisticated with both your favorite sneakers and your booties—two different styles that prove these pants’ versatility. However, they also pair nicely with more trending shapes, like Mary Jane flats, ballerinas, and loafers—all runway-approved, too. Need more inspiration on how to style them together? These outfit ideas might be what you’ve been looking for. Here’s how to wear ’90s straight-leg jeans with flats in 2025.
With Mary Jane Flats
Just as it happened in the ’90s, straight jeans are once again crowned a street styler favorite and are play well with spring/summer 2025’s top shoe trends. Starting with the Mary Jane in white, the schoolgirl aesthetic continues to captivate the most stylish women and these look more sophisticated than you think. The key is to invest in a neutral pair to evoke a sense of maturity, as we see in the photograph. Luxury brands like Alaïa and Toteme, or affordable brands like Massimo Dutti and Zara, have a variety of elegant silhouettes that are season-less style heroes. Take cues from the look above and match your shoes to your jacket for effortless elegance when paired with blue jeans.
With Classic Ballerinas
Denim with ballerinas is a fail-safe combination for the street style set and celebrities alike —Katie Holmes, Gigi Hadid and Lily Collins have all embraced the look at some point. Jean-wise, opt for a design with a folded cuff, or roll up a puddling pair to show off your ballerinas. A black pair in leather or satin in black will be enough to build a winning outfit. Worn together with a white T-shirt and an oversized blazer, it’s a look suitable for a day at the office, morning coffee with friends, or a walk around the city.
With Sneakerinas
Dua Lipa is not the only one who has made the “sneakerina” desirable—the street style set is fond of the shoe shape, too. These give an ultramodern twist to ’90s-inspired denim, from classic medium washes to faded pairs that the new generations love so much. Go for a metallic Adidas pair and complete the look with a plain or graphic print T-shirt—the idea is to project a relaxed style with a hint of grunge.
With Loafers
The great thing about straight jeans is that in addition to being versatile, they have the “perfect” fit that shapes the figure impeccably and flatters everyone equally. Just opt for a clean design to look fabulous without much effort; the best dressed wear them with darted button-down shirts and loafers, a sophisticated yet casual ensemble fit for any scenario. It’s a look that is impossible not to associate with icons of the decade like Julia Roberts or Linda Evangelista.
With Retro Sneakers
Dark wash jeans are not exclusive to fall, they also work for spring months. Don’t hesitate to mix in sporty touches, like a pair of brown Adidas sneakers—the Samba model is ideal if you are looking for comfortable and stylish flat shoes. Add a black T-shirt, a thin belt and a leather bomber jacket for a casual look with tomboyish edge and a trend that models-of-the-moment Loli Bahia and Alex Consani have been responsible for popularizing.
With Statement Flats
Nineties minimalism is not dead. Find proof in Anya Taylor-Joy’s look, which is built around light-wash straight-leg jeans. Take a page from her style book by wearing yours with split-toe Tabi loafers, a strappy blouse and a fitted leather jacket, topping it off with a baseball cap. Modern, sophisticated ,and functional—this look will turn heads with every step you take.
