As the show's inaugural Bachelorette, Trista found love with cute, sensitive firefighter (and now hubby!), Ryan Sutter.
A former Miami Heat cheerleader, Trista had a bangin' bikini bod and wasn't afraid to show it off. On the red carpet and at rose ceremonies, she was all about a simple black dress.
After a rejection from Bachelor Bob Guiney, Meredith was given a second shot at love as the show's second Bachelorette. Meredith liked to showcase her lively, unique personality in pieces like this pink furry jacket.
Meredith ultimately chose Ian McKee as her betrothed, but the pair split up in 2005, a year after the show ended.
Chicago PR girl Jen was initially chosen by Season 3 Bachelor Andrew Firestone, but ended the relationship and became the third Bachelorette.
A city girl at heart, Jen was almost always rocking a great pair of denim.
DeAnna Pappas suffered a painful rejection from season eleven Bachelor Brad Womack, but bounced back with her own season of The Bachelorette.
DeAnna favored bright colors, wild prints, and loved to layer with accessories.
Canadian interior designer Jillian Harris has a natural knack for style, and while her taste in men was in need of a little refining (she inevitable parted ways with finacee Ed Swiderski), her taste in clothing was always impeccable.
We loved tuning into Jillian's season not only for her bubbly, infectious personality, but also for a chance to see what she was wearing. This printed maxi-dress is one of her many memorable outfit choices.
A laid-back California girl, Ali wasn't afraid to mix things up. Wearing a formal evening gown with a pair of Converse? No problem!
Ali loved a vibrantly-hued dress almost as much as she loved contestant Roberto Martinez. Unfortunately, the love didn't last -- the pair split up in 2011.
Former dancer Ashley's wardrobe staple throughout the season was a silky, button-down top like this one.
Ashley is the second Bachelorette to have successfully found love on the show -- marrying contestant JP Rosenbaum in December 2012.
After dumping Brad Womack, Emily moved on to her own season of The Bachelorette, and a fabulous wardrobe to boot.
Southern girl Emily liked to remind viewers of her North Carolina roots, and ditched the formal gowns as often as she could.
Desiree's season of the Bachelorette was full of tears, mostly from Desiree herself. Her laid back, sporty style was what really made her shine.
After losing Sean Lowe's love, Desiree became the Bachelorette and found her fiance, Chris during the season.
Wearing a gorgeous pale white frock with beaded neckline, Andi looks amazing.
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On Monday, fans of The Bachelorette will finally be rewarded with a new fix, as former Bachelor contestant Desiree Hartsock gets her second shot at love on the show's season premiere.
In honor of the new season, and the beginning of Desiree's journey to the altar, we're taking a look back at the Bachelorettes of seasons past -- and more specifically, their enviable wardrobes.
Though Season 1 premiered only ten years ago, in 2003, styles have certainly changed since Trista Rehn (now Sutter) took the stand at her first rose ceremony. Along the way, we've seen our fair share of fashionistas past through, including the ultra-stylish interior designer Jillian Harris, current television host and laid-back California girl Ali-Fedotowsky, and stylish Southern Belle (and mom!), Emily Maynard.
Click through the gallery for a trip down memory lane and decide for yourself who earns the rose for the best-dressed Bachelorette!