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And just like that, baggy jeans are back. This year, the early 2000s denim style that prominently features wide-legged, floor-skimming, and boxy silhouettes has returned in full force. Baggy jeans are certainly comfortable, but when your pants are big enough to cover your feet, what shoes do you wear with them?
A wide variety, it turns out. As evidenced by 2024’s street style set, baggy jeans can be worn on any occasion in a myriad of ways—as well as numerous denim washes and lengths, making the trend truly versatile for any fashionista. Styles that hit the ground can be literally boosted with a set of boots with ‘90s-inspired narrow toes, prints, or thick block heels. Trendy shoes like ballet flats (we fawn over the Chanel variant) also provide a whimsical complement, as do clever styling tricks like cuffing or tucking hems to further showcase your footwear.
Of course, classics never go out of style, no matter how trendy the denim they’re paired with. Silhouettes from classic white sneakers to sharply pointed pumps have also been worn with the style, bringing a nostalgic and approachable finish to the biggest new jeans silhouette.
Below, take a glimpse at eleven street-style-approved shoes to pair with your baggy jeans.
Metallic Flats
It’s no secret that ballet flats are on a hot streak right now. They provide a chic alternative to sneakers and a comfortable counterpart to heels. A metallic hue in shiny gold or silver can be matched with accessories like jewelry or bag hardware for a coordinated appearance, making a statement while remaining easy to wear.
Kitten Heel Pumps
Similarly to ballet flats, kitten-heeled pumps provide a comfortable, low-height shoe option that’s also sophisticated and chic. Their subtle 1-2-inch height boost also keeps your jeans’ hems from completely touching the ground. A dark, neutral pair in any leather finish will sharply finish any ensemble.
Square-Toed Sandals
For a true 2000s look, slip on a pair of square-toed sandals the next time you wear baggy jeans. The style’s geometric base will make a sharp statement against the denim’s long hemlines, while high or thicker heels can uplift them from sliding on the ground. If you want to test the look without catching a cold this winter, take a cue from Katie Holmes and layer yours with colorful tights
Narrow-Toed Boots
Try pairing your baggy jeans with a set of narrow-toed boots for a dash of nostalgia. Faintly squared yet closed toes provide a sharp finish with a geometric edge while still chicly hinting at the ‘90s and early 2000s eras. For added vintage inspiration, lean into neutral tones like dark brown or black in matte or patent finishes—which can still be worn for years to come.
Slouchy Boots
If you’re not keen on letting your jeans’ hems dangle near the ground, don’t do it at all. Instead, tuck them into a set of boots with slouchy shafts. Whether low or high-heeled, the shoe’s larger openings will allow your denim to retain its upper silhouette with a new dimension. Or, if you prefer, you can always wear them over the boots as well.
White Sneakers
White sneakers never go out of style and can be worn with any type of denim—even baggy jeans. Low-top, lace-up pairs in materials like suede or leather provide a clean base, with rubber soles allowing for easy movement. A hint of tonal colors or patterns, as seen on the streets of New York Fashion Week, can also bring the minimalist style a personal touch.
Embellished Low-Height Heels
With their closed toes and heeled base, low-height pumps and mules provide an elevated complement to baggy jeans. Pairs with mesh or sheer fabric uppers provide a comfortable base, while embellishments like crystals, metallic jacquard or shiny trim finish your shoes—whose toes will be the most visible—with a dash of glamour.
Block-Heeled Boots
As a classic wardrobe staple, the block-heeled boot is an easy match with baggy jeans. In any heel height or tone, the shoe provides a balanced base that will keep your hems off the ground while ensuring you also have full foot coverage. Like any go-to shoe, versatile colors like black, brown or beige will work best—though when it comes to height, anything goes.
Colorful Sandals
For a whimsical statement, boost your baggy jeans with brightly colored sandals. Stiletto and block-heeled styles will bring you a sharp height boost, while punchy yellow, pink, and orange hues will make a statement against denim’s dark tones. Details like thick heels and platform soles—plus styling tricks like cuffing your hems—will also place greater emphasis on the shoe.
Animal-Print Boots
Why not play with prints when styling your baggy jeans? Take a walk on the wild side and elevate the voluminous denim with an animal-printed boot. The fuller coverage and range of heel heights allow for versatile wear, while patterns mimicking cheetahs, cows and snakes will bring the casual bottoms a dynamic edge.
Sharp Pumps
A pointed-toe pump will never go out of style—even when paired with trendy, of-the-moment denim. Smooth leather or suede iterations in classic black or brown will create the sharpest contrast to your baggy jeans, creating a nonchalant and chic finish. Denim with hems that are frayed or higher up the leg will also allow for the shoe to make a greater statement with every step.