9. Jen Schefft - Season 3 Via img2-3.timeinc.net Jen didn't get engaged her finale; no proposal = no gown. 8. DeAnna Pappas - Season 4 Via dailymail.co.uk There's nothing wrong with DeAnna's blue-green empire waist dress, but there is nothing right, either. With its silky material and empire waist, it feels like a prom dress and not in a good way. 7. Meredith Phillips - Season 2 Via ruggedelegantliving.com Season 2's Meredith kept it simple and classic in a white button down and black skirt. It's a casual look in comparison to the prom gowns of recent seasons. 6. Trista (Rehn) Sutter - Season 1 Via ew.com How can you not love Trista? The first Bachelorette wore a white-gray lacey dress with an adorable up-do. 5. Jillian Harris - Season 5 Via celebritybrideguide.com Jillian's pink gown was sweet and simple. 4. Des Hartsock - Season 9 Via eonline.com While Des wasn't the most fashionable Bachelorette, her finale gown fit her beautifully and really complemented her skin. 3. Emily Maynard - Season 8 Via wetpaint.com It wouldn't be Emily Maynard if it weren't over-the-top and sparkly, but that's why we love her. Plus, she looked so tan in this peach gown. 2. Ali Fedotowsky - Season 6 Via celebritybrideguide.com Ali, another fan favorite, looked gorgeous in her golden gown. The beautiful color and woven bodice paired perfectly with her beachy, natural hair. 1. Ashley Hebert - Season 7 Via celebritybrideguide.com This gown had everything: the color, the cut, the embellishment. Ashley nailed it with this dress and proved once and for all she deserved to be the Bachelorette.