Jennifer Aniston Has Worn This Pant Style Since the '90s — and She's Never Looked Back

Nothing separates Jennifer Aniston from her jeans. There is simply no season or occasion she won't try them on for, as we've learned over the years while tracking her style. From red carpets to date nights, Jen has proven that denim isn't just a sign of a casual look. While she's admitted skinny jeans aren't her favorite in the past, and she clearly knows how to rock a slouchy fit, the star's managed to come up with a handful of ideas for every silhouette in the book. Read on for a few of her most trustworthy lessons, some of which come from the '90s but can still easily be applied today.

Jen's Lockdown Denim Went Best With a Cozy Sweater and White Velcro Sneakers
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Jen's Lockdown Denim Went Best With a Cozy Sweater and White Velcro Sneakers

Jen Allowed a Textured Patent Leather Belt to Break Up Her Darkest Denim
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Jen Allowed a Textured Patent Leather Belt to Break Up Her Darkest Denim

Jen Wore Her Boyfriend-Cut Jeans With a Bomber
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Jen Wore Her Boyfriend-Cut Jeans With a Bomber

She Owns Cropped, Straight-Legs That Go Right Down to Her Boots
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She Owns Cropped, Straight-Legs That Go Right Down to Her Boots

Jen's Ripped Boyfriend Jeans Balanced Out a Luxe Coat and White Sneakers
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Jen's Ripped Boyfriend Jeans Balanced Out a Luxe Coat and White Sneakers

Skinny Jeans Lent a Casual Touch to a Sophisticated Blazer
Getty | Raymond Hall

Skinny Jeans Lent a Casual Touch to a Sophisticated Blazer

Jen's Olive-Tone Denim Worked With a Handful of Neutrals
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Jen's Olive-Tone Denim Worked With a Handful of Neutrals

She Paired Her Boyfriend Jeans With a White Shirt and Black Blazer
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She Paired Her Boyfriend Jeans With a White Shirt and Black Blazer

Boot-Cut Jeans Broke Up a Black Jacket and Brown Boots
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Boot-Cut Jeans Broke Up a Black Jacket and Brown Boots

Jen Paired These Bootleg Jeans With the Perfect Boot
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Jen Paired These Bootleg Jeans With the Perfect Boot

Slouchy, Rolled Denim Looked So Cool With a Sweater and Fedora
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Slouchy, Rolled Denim Looked So Cool With a Sweater and Fedora

She Paired Ripped Boyfriend Jeans With Strappy Heels and a Polka-Dot Blouse
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She Paired Ripped Boyfriend Jeans With Strappy Heels and a Polka-Dot Blouse

Jen Showed Off Her Functional Brogues by Rolling Up This Pair
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Jen Showed Off Her Functional Brogues by Rolling Up This Pair

Jen Paired Bell-Bottoms With a White Button-Up Blouse
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Jen Paired Bell-Bottoms With a White Button-Up Blouse

She Slipped Into Her Light-Wash Skinnies With Sandals in the Summer
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She Slipped Into Her Light-Wash Skinnies With Sandals in the Summer

Jen's Worn Booties and Socks With Her Jeans
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Jen's Worn Booties and Socks With Her Jeans

Jen Made Her Dark Denim Look Like the Perfect All-Black Outfit With Pops of Gold
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Jen Made Her Dark Denim Look Like the Perfect All-Black Outfit With Pops of Gold

She Knows They Work Best in Any Silhouette With a White Tee
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She Knows They Work Best in Any Silhouette With a White Tee

Jen Always Seems to Wrap a Scarf Around Her Neck When She's in Her Fall Denim
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Jen Always Seems to Wrap a Scarf Around Her Neck When She's in Her Fall Denim

Jen Used Her Jeans to Play Up a Military Green Anorak and Wide-Brim Hat
Getty | Raymond Hall

Jen Used Her Jeans to Play Up a Military Green Anorak and Wide-Brim Hat

Jen Chose a Relaxed Boyfriend Jean on a Rainy Day
Getty | James Devaney

Jen Chose a Relaxed Boyfriend Jean on a Rainy Day

For Date Night, Jen Styled Her Belted Flares With Platform Sandals and a Basic Tank
Getty | Alo Ceballos

For Date Night, Jen Styled Her Belted Flares With Platform Sandals and a Basic Tank

Jen Wears Her Denim Through Winter With Lots of Layers
Getty | James Devaney

Jen Wears Her Denim Through Winter With Lots of Layers

She Likes a Polished Look Too — All Belted and Tucked In
Getty | Ray Tamarra

She Likes a Polished Look Too — All Belted and Tucked In

In 2009, Jen Exhibited Unexpected Coolness in Some Low-Slung Denim
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In 2009, Jen Exhibited Unexpected Coolness in Some Low-Slung Denim

Jen Pulled off a Parisian Chic Look in 2004 By Wearing Her Jeans With a Beret
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Jen Pulled off a Parisian Chic Look in 2004 By Wearing Her Jeans With a Beret

Jen Wore a Taupe Wrap Sweater With Her Jeans and Booties
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Jen Wore a Taupe Wrap Sweater With Her Jeans and Booties

Back in 1998, She Made Mom Jeans Look Fabulous With a Sheer Blouse and Platforms
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Back in 1998, She Made Mom Jeans Look Fabulous With a Sheer Blouse and Platforms