21 Early ’00s Ashlee Simpson Outfits That Now Seem Highly Questionable

Dress capris: We’ve all been there.

1. The early 2000s: A time when we all cut the necklines out of our T-shirts. Because they did not deserve to be there.

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2. The early 2000s: A time when cargos could be cuffed into capris and people would still like you.

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3. The early 2000s: A time when baggy jeans were red carpet attire.

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4. The early 2000s: A time when skinny scarves provided protection from the elements.

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5. The early 2000s: A time in which sequined shrugs complimented army fatigues.

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6. The early 2000s: A time when we wore…um, whatever these pants are called? Gaucho pants?

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7. The early 2000s: A time for capris, all the time.

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8. The early 2000s: A time for layering jewelry, tank tops, everything.

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9. The early 2000s: A time for tiny jackets.

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10. The early 2000s: A time for even tinier jackets.

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11. The early 2000s: A time for dominatrix boots over jeans.

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12. The early 2000s: A time for distressed flare jeans.

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13. The early 2000s: A time for graphic butt pants because it was the best place to put a design.

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14. The early 2000s: A time for sexy, belted tops.

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15. The early 2000s: A time for incredibly tall Adidas.

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16. The early 2000s: A time for dresses that don’t give a fuck if pants are around.

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17. The early 2000s: A time for kitten heels. SoooOOOoo many kitten heels.

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18. The early 2000s: A time for…blerg. I don’t know.

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19. The early 2000s: A time for…this.

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20. The early 2000s: A time for…being sad about outfits like this.

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21. The early 2000s: WHYWHYWHY.

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