I can trace my love affair with 90s loafers back to an impulse buy in TK Maxx four years ago. I found a chunky Steve Madden pair buried between mismatched boxes, wore them to the office almost every day for a year and worked up a split in the sole after stomping 10,000 daily steps in them on my commute. They’re still the only shoes I’ve ever repurchased twice - which says everything you need to know.
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There’s something about a pair of loafers that just works, no matter what else you’re wearing. A slip-on shoe by design, defined by its low heel, rounded toe and often finished with a penny strap or tassel, loafers are the kind of staple that every fashion girl needs in her wardrobe. Originally rooted in menswear - worn by businessmen as a practical, comfortable alternative to lace-ups - loafers carry that same preppy energy into the everyday wardrobe. By the 1990s, fashion ‘’It-girls' like Carolyn Bessette had claimed the loafer for themselves: styled with bare legs, oversized shirting, and minimal tailoring.
It’s a formula that still holds. Case in point: when Hailey Bieber stepped out in denim shorts and loafers, all I could think of was: “I saw Cady Heron wearing army pants and flip-flops, so I bought army pants and flip-flops”. The appeal is in how unfussy they are. They ground an outfit, add structure, and somehow make even the most casual pieces feel pulled together.
Thanks to Love Story: John F. Kennedy, Jr. & Carolyn Bessette, my Pinterest moodboard is an ode to 90s fashion, and the loafer is a common theme. This versatile shoe works just as well with office-ready tailoring as it does with breezy summer skirts or vintage denim. Worn with socks for a more preppy feel, or kept bare for something cleaner, they can shift depending on the outfit. Dressed up or pared back, they move easily between moods - which is exactly why they’ve endured.
Keep scrolling to read exactly how a fashion writer would style 90s loafers.
With a preppy oversized shirt
Spotted on Kendall Jenner in Manhattan, the oversized shirt and loafer pairing leans into that borrowed-from-the-boys ease the 90s did so well. A crisp, slightly exaggerated shirt worn loose over bare legs or tailored shorts keeps things relaxed, while a sleek patent loafer sharpens the look just enough. It’s the kind of outfit that works for city days when you want something simple but still pulled together - minimal effort, maximum payoff.
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With denim shorts
If there’s one outfit that proves loafers aren’t just for autumn, it’s Hailey Bieber in denim shorts. The contrast is what makes it work: casual, slightly slouchy shorts paired with a polished leather loafer. Keep the rest of the outfit clean - think a white tee or a lightweight knit - and let the shoes do the grounding. It’s an easy way to make summer staples feel a little more elevated without overthinking it.
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With a breezy lace skirt
A lace skirt with loafers taps into that 90s mix of soft and structured. Seen across Copenhagen Fashion Week on style influencers like Linda Sza, the pairing offsets delicate fabrics with a more polished shoe. A black lace slip skirt styled with classic leather loafers keeps things balanced - add a simple knit or tee and it feels modern rather than overly dressed.
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For a slightly bolder take, look to Simone Ashley, who leans into chunkier soles for added impact. For me, a chunky loafer is the shoe equivalent of boyfriend jeans. A heavier loafer brings a masculine-esque contrast to softer silhouettes - think mini dresses, tailored shorts or even straight-leg trousers. The added weight gives the outfit a bit more edge, without straying too far from the classic 90s feel.
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With knee-high socks
Knee-high socks and loafers are a direct nod to 90s styling (note, Britney Spears in the …Baby One More Time music video). As the street style set have proven ,the combination works best when the rest of the outfit is clean and structured - think a cropped jacket or tailored skirt. It adds a preppy finish without tipping too far into school-uniform territory.
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With a summer skirt and socks
A breezy summer skirt paired with loafers is case in point that loafers really do go with everything. Lightweight fabrics - like a cross-over or slip-style skirt - keep the look soft, while a classic brown or black loafer adds structure. It’s an easy swap for sandals when you want something a little more put-together but still seasonally appropriate.
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With wide-leg jeans
Dakota Johnson has long mastered the art of simple, wearable styling, and wide-leg jeans with loafers is a go-to. The key is in the proportions: a longer, looser jean that just skims the shoe, paired with a fitted tee or relaxed shirt. The loafer keeps everything grounded, giving denim a slightly more polished edge without losing its ease.
With an oversized blazer
An oversized blazer and loafers is about as 90s as it gets. The look plays with proportion - structured on top, streamlined at the shoe. Add socks if you want to lean further into the aesthetic, or keep it bare for something cleaner. Either way, it’s a reliable formula that works from office to off-duty.
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