Everyone Is Dressing the Same. Fiona Apple Never Did.

Anasa Fraser
1 hour ago
4 min read

Fiona Apple's styling still resonates today because none of it was built for approval. Every reference board right now looks pre-approved: clean girl neutrals, the same five brands, an outfit so smoothed over it might as well be AI-generated. Fast fashion chases that same flatness from the other direction, a rush job dressed up as a finished idea.

There's been a cultural leaning toward sameness over the past thirty years, and now the pendulum is swinging the other way. A look in the rearview, toward times that felt better, simpler, more stylish, more individual. A willingness to look at yourself honestly and reflect that outward.

Looking through Fiona's photos from the late '90s and early 2000s, we see repeats of fabrics, silhouettes, and, best of all, styling habits. She came up in a mid-90s pop landscape that ran on Spice Girls maximalism and Britney's manufactured girl-next-door polish, with stylists, hair and makeup teams, and wardrobe departments working overtime to build a persona. She wasn't the pop star that industry expected a nineteen-year-old woman to be, and her clothes said as much: roomy, dark, and most meaningfully hers, especially beside the polished pop machine around her.

Today, you can see the pull back toward this, a combination of sexy and a little sloppy: messy chic summer looks, low-rise revival, and the consistent and desperate hunt for Tom Ford Gucci. All of it is nostalgia doing double duty, a longing for the '90s and a longing to feel like a person again. You can trace a lot of it back to Fiona.

Tanks & Camisoles

If one garment anchors Fiona's wardrobe, it's the humble tank top. Every iteration feels like fair game: silk camis with lace edging, paired with low-rise trousers. Slinky tube tops, worn over contrasting bras. Simple cotton tanks, fitted or oversized, some perfectly threadbare, others plucked fresh from a multi-pack.

An unfussy styling tip: She constantly ties her tops at the waist, very reminiscent of high school gym days. It shortens the silhouette, gives shape without tailoring, adds texture, and leaves just enough midriff to have me contemplating a belly ring. Should we bring those back? I'm tempted, and inspired.

When shopping for secondhand camis, look for silk or rayon over polyester. They hang and catch light much nicer than polyester does. Cotton jersey with some wear on it drapes more beautifully than anything off the rack, and cropped doesn't have to mean tight. Look for interesting color combinations, frayed edges, and don't shy away from strange patterns.

Secondhand search terms: lace-trim silk camisole, rayon camisole, tube top, ribbed cotton tank, cotton jersey tank. For the era, Victoria's Secret and Express Design Studio both made this exact silhouette in the '90s.

Trousers & Skirts

Many of my favorite outfits of Fiona’s are from her off-duty looks. A woman after my own heart, her outfit formula is a tiny top with large pants, allowing for maximum movement, whether on or off stage. Low-rise trousers skim the hips before dropping into a bootcut leg. Jersey skirts catch the wind, and are paired with comfortable footwear, like slides, clogs and trainers.

The secondhand market is a treasure trove for simple, elegant bottoms. For trousers, look for corduroy or something tailored, low-waisted, in dark, moody colors like wine, berry, and black. She usually kept these simple, in contrast to her occasionally printed or embellished tops.

Secondhand search terms: low-rise trousers, bootcut trousers, corduroy trousers, jersey skirt, wine or berry midi skirt. For the era, Diesel, Guess, and Levi's all did this low-rise, moody-colored silhouette well.

A Folksy Touch

Despite minimal styling, the looks never slip into the category of minimalism because of their texture. She reached for it in different forms, some structured, some loose. Filet crochet is dense and patterned, best shown in this dress worn to the 1997 VMAs, with a floral motif at its scalloped, uneven hem, sitting over what looks like a white bra and slip skirt. Elsewhere, it's draped: a dyed silk maxi dress, a two-piece cotton jersey set worn on stage, both loose and fluid.

Accessories carried their own texture, too. Chains and beads sat at her natural waist or low on the hip, layered easily against a warm, earthy palette, think bruised fruit: tobacco, olive, chocolate, faded burgundy. Frayed edges, lace, velvet, corduroy, jersey, none of it precious.

Hand-crocheted pieces are worth hunting for secondhand: they're usually more affordable than buying new, the designs are one of a kind, and the quality tends to hold up. For the accessories, check craft and hardware stores for chains by length. Most waist chains are just a chain and a clasp, and you can build your own for less than a finished one costs. Don't skip the men's section or vintage watch bins either, chunky link chains built for wrists work just as well around the waist.

Secondhand search terms: filet crochet dress, hand crochet maxi dress, dyed silk maxi dress, cotton jersey two-piece set, and waist chains. For the era, Anna Sui and Marc Jacobs's 1993 grunge collection for Perry Ellis both put crochet and macramé on the runway that season.

Aside from her music, one of Fiona's most quoted lines is from that same era. Accepting her 1997 VMA for Best New Artist in a Video, she told the room;

"This world is bullshit... You shouldn't model your life about what you think that we think is cool and what we're wearing and what we're saying and everything. Go with yourself."

Spend enough time looking through Fiona Apple's wardrobe, and the same ideas keep returning. Silk, cotton, crochet, low-rise trousers, and always integrate texture where you can. None of these are especially difficult to find. The interesting part is learning to recognise them.