The Bachelor Dresses: Which First Night Styles & Colors Had the Highest Success Rate?

Photo: courtesy of ABC.
New year, new season of The Bachelor, same parade of sparkly, over-the-top rose ceremony gowns. And perhaps for good reason. Each year, when the latest season of ABC’s smash reality dating show airs, fans nationwide gather around their TVs with glasses of rosé ready to judge 30 complete strangers based on their highly edited conversations with the Bachelor, their interactions with one another and, importantly, what they choose to wear on their first night at The Mansion.
But if Bachelor history has taught us anything, it’s that there is always a method to the madness, even and especially when it comes to what the contestants wear the first time they meet their potential husband-to-be. In the 22 seasons that The Bachelor has been shaping our understanding of true love, 14 have ended in a proposal, with all the other Bachelors and their winners opting to continue their relationships after the season’s end (except for Brad Womack, who famously left both his finalists ringless and alone in the stunning Season 11 finale).
So was there something about those winners that stuck out to the Bachelor from night one? Was it a particularly flattering dress — or just the way she wore it with confidence? With Season 23’s first rose ceremony in the rearview mirror, we’re curious to see if a contestant’s fashion choices can indeed predict her success on the season and beyond. Do figure-hugging bandeau dresses a Bachelor winner make? Do Bachelor stars prefer gowns that show more skin or less? And what, oh what, is a contestant to do if they find out that someone else is wearing the same dress as them? Trick question: this just happened on the Season 23 premiere, and the answer is ... not much.
Here, we look back at the color, cut, and style of dresses that each of the winners from the past 22 seasons wore during their premiere episode, in hopes of figuring out whether or not there’s a telltale style that signals true love to our lovelorn Bachelors. (Our guess is that the sloth costume doesn’t quite make the cut.)
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Season 1: Amanda Marsh (Alex Michel)

This was the season that started it all. And Amanda, the eventual winner of the show, captured Bachelor Alex’s attention from the get-go in a no-holds barred, sexy low-cut shimmery red dress that put her best, erm, curves forward.
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Photo: Bob D'Amico/ABC/Getty Images.
Season 2: Helene Eksterowicz (Aaron Buerge)

Helene’s tactic going into the second season of The Bachelor seemed to be to fly high with class (even though Bachelor Aaron was known to be pretty pompous); it should come as no surprise that the pair broke up after several weeks of dating. On night one, however, Helene put her best foot forward in a black one-shoulder gown that was both classy and classic, if unmemorable.
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Season 3: Jen Schefft (Andrew Firestone)

Jen, who would go on to be the third Bachelorette star, kicked off her journey with Bachelor and tire heir Andrew Firestone in a sweet and simple frock, a knee-length black dress with thick, ruffled straps and a dotted pattern that ran down the front of the bodice.
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Season 4: Estella Gardinier (Bob Guiney)

Estella and Bob’s relationship was flashy , but fleeting, ending shortly after their season of The Bachelor aired back in 2003. On night one, however, Estella made a quiet impression on Bob in a simple black gown (with short sleeves!) that proved her personality would take the lead in their first impression.
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Season 5: Jessica Bowlin (Jesse Palmer)

Though Jessica and Jesse’s romance was short-lived (they dated for just several weeks after the season finale), Jessica went into the show with high hopes, maybe made evident by her choice of gown: a white, satin floor-length halter dress that no doubt was meant to be reminiscent of a wedding gown.
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Season 6: Mary Delgado (Byron Velvick)

Mary’s entrance onto The Bachelor stage was a graceful one, in a sky blue, floor-length gown that signaled calm and confidence,and which stood out (in a good way!) in contrast to that season’s many black gowns.
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Season 7: Sarah Brice (Charlie O’Connell)

Sarah and Charlie had quite the love story, dating for two years following the series finale, breaking up for a year over Charlie’s drinking problem, and then reuniting for two more years after that, only to split up in the end. On night one, however, Sarah began her Bachelor journey in characteristic, fresh-faced fashion, with a simple black, glittery halter dress.
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Photo: Bob D'Amico/ABC/Getty Images.
Season 8: Sarah Stone (Travis Lane Stork)

Before he was an expert panelist on The Doctors, Dr. Travis Lane Stork was the Bachelor, and he gave his heart to Sarah Stone in Paris. The couple’s first meeting went swimmingly, with Sarah in a relatively conservative, albeit sparkly, black sleeveless gown that hugged her figure and showed off just a hint of cleavage.
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Photo: Craig Sjodin/ABC/Getty Images.
Season 9: Jennifer Wilson (Lorenzo Borghese)

The ninth season of The Bachelor was also known as Bachelor: Rome because the entirety of the season was, in fact, filmed in Rome, and Lorenzo was a literal prince. Winner Jennifer Wilson dressed the part of understated glamour with a shimmery black halter dress that clearly caught the prince’s eye.
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Season 10: Tessa Horst (Andrew Baldwin)

Tessa’s dress from Season 10 was perhaps most memorable for its relatively risque nature. The San Francisco-based social worker lit up Andrew’s face right off the bat (his first comment to her was, “Wow, you’re sparkly”) with a black, floor-length halter gown with sequined trim and several strategically placed, seemingly sheer panels running down the length of the dress.
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Season 11: none (Brad Womack)

Technically speaking, no one won Brad’s first season as the Bachelor, because the Atlanta native ended up turning down both DeAnna Pappas and Jenni Croft in a truly historic Bachelor moment that enraged fans and cast Brad as the most disliked Bachelor of all time. For what it’s worth, however, DeAnna wore a bold black-and-white striped strapless dress with a fun 50s hemline, and Jenni wore a short, strapless black dress with a little twirl in the skirt.
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Season 12: Shayne Lamas (Matt Grant)

When Shayne first met Matt, she was still a relatively unknown entity (flash-forward to post-Bachelor life, when Shayne and her family starred in the short-lived reality series Leave It To Lamas), and her outfit for the first night reflected that: the actress wore a black floor-length gown with little distinguishable features other than two thick, criss-crossing straps.
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Season 13: Melissa Rycroft (Jason Mesnick)

Before there was Arie and Becca, there was Jason and Melissa, he who pulled a 180 swap on his winner only to get together with his runner-up. From night one, however, Melissa exuded class, in a simple black satin strapless floor-length gown and a diamond necklace to accessorize.
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Season 14: Vienna Girardi (Jake Pavelka)

Drama seems to follow Vienna wherever she goes, but back in 2010, when America first met the marketing representative from south Florida, she was still relatively unassuming, donning a glittery olive green, floor-length dress with thin straps and a sheer black mesh overlay, reminiscent of an early aughts prom dress.
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Season 15: Emily Maynard (Brad Womack)

Sweet-natured Emily emerged from the limos on night one with a big grin on her face and just the kind of quiet confidence that attracted Brad right off the bat. It didn’t hurt that her night one look was simple and unfettered, either: a black floor-length, off-shoulder gown with a sweetheart neckline and a glittery crystal waistband just to add a little pizazz, with perfectly curled hair to complete the look.
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Season 16: Courtney Robertson (Ben Flajnick)

Courtney didn’t go on The Bachelor to make friends (she even wrote a book titled I Didn’t Come Here to Make Friends, just in case anyone was unsure of her motives). So it makes sense that the model-turned-reality TV villain dressed the part for her first night at The Mansion, donning a classic little black dress — complete with spaghetti straps and towering heels — that showed that she didn’t need to employ any frou-frou, over-the-top antics on the show to win.
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Season 17: Catherine Giudici (Sean Lowe)

As the only contestant who is still married to the Bachelor who chose her, Catherine deserves a standing ovation — and perhaps even a few social media follows, should Bachelor Nation be so generous. From night one, it was clear that Sean was smitten with Catherine, and who can blame him? She wore an eye-catching, midnight blue strapless number that was sparkly up top and solid-colored below, which got her an immediate compliment from Sean (“You look beautiful!”) without trying too hard.
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Season 18: Nikki Ferrell (Juan Pablo Galavis)

Nikki and the rest of the contestants on Season 18 put up with a lot given Juan Pablo and his egotistical antics (to this day, he’s still considered one of the most reviled Bachelors), but before all of the emotional drama and trauma went down, Nikki decided to give it her all in a stunning black, backless gown with gold sequined patterns that showed off her figure without being too flashy.
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Season 19: Whitney Bischoff (Chris Soules)

Whitney chose to go classy and understated for her first dress of the season in a shorter black number with cap sleeves and a few well-placed cutouts to show off her décolletage. The shorter cocktail dress style was definitely “in” for Chris’ season, but her fashion sense still wasn’t enough to hold the Bachelor’s interest in the long run; the pair split two months after he popped the question during the season finale.
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Season 20: Lauren Bushnell (Ben Higgins)

Lauren had the high honor of being the first to step out of the limos on Ben’s season of The Bachelor, and her bubbly personality shone through in her flight attendant intro (complete with a set of wings that she gifted him) and her pale blue, strapless Sorella maxi dress from Lulus, which set her apart from many of the other contestants’ sparkly or bright red getups.
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Season 21: Vanessa Grimaldi (Nick Viall)

Vanessa may have made quite the impression on Nick Viall with her limo entrance (telling him “I’m very happy to be here with you” in French), but her night one gown was far less memorable: a low-cut black number with a white linear design that accentuated her features, but looked like something straight out of Austin Powers.
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Season 22: Becca Kufrin (Arie Luyendyk Jr.)

Becca (better known as Becca K. throughout the season, not to be confused with fiery Bekah M.) had Arie down on one knee from night one in an elegant floor-length black lace halter dress that showed off her toned shoulders, with a peek-a-boo sheer cutout in front for some extra sass.
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Season 23: ?? (Colton Underwood)

And the verdict is in: based on the past 22 seasons of The Bachelor, it appears as though a pattern has emerged: flowing, floor-length, shimmery (but not sequined!) black halter gowns have historically been the choice of dress for the eventual winners of each season — with a few exceptions, of course. Based on that criteria alone, we have our money on the following Bachelor hopefuls: Katie, Hannah B., and Sydney. But given the unpredictability of the series, the roses are still very much up for grabs, regardless of the contestants’ taste for glitter.

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