Ranking the 27 dresses of 27 Dresses
'The best thing is you can shorten it and wear it again.'
There’s a lot to enjoy about 27 Dresses — Judy Greer’s stellar turn in yet another snarky best-friend role, James Marsden finally getting the girl in a movie, that joyous ‘Bennie and the Jets’ scene — but the biggest scene-stealers are right there in the title: Jane’s (Katherine Heigl) 27 bridesmaids’ dresses, which range from mildly inoffensive and drab to downright mental.
As Marsden’s Kevin Doyle asks, “What was the theme? Humiliation.”
With its wry sense of humor, the movie both celebrates and takes down the tradition of ugly bridesmaids’ dresses with glee. The line spoken by brides throughout the film — that the dresses are great because you can “shorten them and wear them again” — is a refrain that sums up the hypocritical nature of the wedding industry, which stands at odds with a hopeless romantic’s genuine heartfelt desire to celebrate their friends and their love.
In a delightful montage, we see Jane, the film’s perpetual bridesmaid, try on a wide array of her most cringe-worthy dresses, after catching a glimpse of her closet exploding with pastels, ruffles, tulle, and matching handbags.
Director Anne Fletcher told EW that she and costume designer Catherine Thomas strived to walk the line between finding the most outlandish dresses they could and not losing sight of reality. “I would say, ‘Get the ugliest that you can actually find that would make sense in someone’s wedding. Let’s not be uber stupid, let’s be the dumbest where the line is reality,'” says Fletcher. “I said I wanted colors and sequins and big and all the tulle, hats, anything ridiculous. We had fun with those themes — trying to stay grounded but yet being funny and ridiculous even though it’s very real for us.”
Thus, in celebration of the film’s ten-year anniversary, here are Jane’s 27 dresses — ranked from worst to best (and to be clear, almost all of these belong on a worst-dressed list).
27. Scuba dress
Women already feel self-conscious in a bridesmaid dress and you’re going to make them wear what amounts to a swimsuit to your wedding? This bride is straight up sadistic. The floral Esther Williams swim-caps and pink scuba masks only add to the cringe factor. And I have to ask — did the bride and groom pay for the whole wedding party to take scuba diving lessons???
26. Cha-Cha dress
I wasn’t aware that people had Cha Cha di Gregorio/Carmen Miranda-themed weddings. Why would anyone ever choose a dress that looks like it vomited yellow and pink tulle? The beaded bodice is lovely, but the skirt and the color combo are this dress’ undoing.
This black dress with a purple lace collar might be pretty under different circumstances, but I cannot get past that spiked dog collar necklace and Beetlejuice-worthy make-up.
24. Green taffeta
I don’t even know where to start with this one. What’s the worst part? The over-sized mutton-chopped sleeves that belong in another decade? The heinous cut that somehow manages to make Katherine Heigl look stocky (those shoes don’t help)? The inexplicable black evening gloves? Everything about this is a fashion disaster.
23. Pretty in Pink
The only thing worse than the monstrosity that is Molly Ringwald’s homemade prom dress in Pretty in Pink is that women would be inspired to base their bridesmaids’ dresses off of it.
22. Top Hat
Is this a bridesmaids’ dress or a costume for a backup dancer in a Liza Minnelli musical number?
21. Pink satin
What year were the weddings Jane was in? Why does this look like it belongs on Meryl Streep in Heartburn? We don’t know — we just know we feel sorry for the amount of real women who probably had to wear a dress like this.
20. Navy blue lace
There is way too much going on here — navy blue lace overlay, poufy skirt, some odd mix of girly lace and rustic chic — and all of it is hideous. The dress is frumpy to boot. This whole film works hard to make movie star Katherine Heigl into a plain Jane, but this dress is by far the dowdiest thing she wears.
19. Gone with the Wind
Frankly, my dear, this dress is an antebellum nightmare — the sickly yellow color, the flounces, the oversized orange roses, the bonnet — all of it has me wishing for a tomorrow without this dress (after all, it is another day). Side note: I used to want a Gone with the Wind-themed wedding and then I saw this movie and realized that was a HORRIBLE idea.
18. Red tulle
This would look so cute on the flower girl, but I don’t think that’s what Jane was supposed to be at the wedding.
17. Cowgirl chic
There are definitely better ways to do the rustic, cowgirl vibe at your wedding than this full-on rodeo girl ensemble — but it’s one of the less egregious theme weddings Jane attends. Plus, she does look kind of cute in the hat and the turquoise scarf.
While the lavender color here is lovely, this look is the epitome of a bad bridesmaids dress in that I’m sure it costs a fortune and there is literally no way Jane will ever have a real reason to wear it again.
15. Orange ballerina
This dress, which is reminiscent of something the Sugar Plum Fairy might wear, is actually kind of adorable — if only it didn’t feel like it was selected by a ballet-obsessed 8-year-old.
14. Blue lace
I imagine this dress would be very in vogue for one of two scenarios — being a 1980s bridesmaid, or as nuptial attire for a lesser-known Viscountess at a Royal Wedding. As Jane is neither of those things, it’s a definite fail, though I have to give her credit for rocking the slightly askew hat. Plus, that lace bodice is pretty — just not on this dress.
13. Beaded blue floral
This dress is fantastic if you’re attending your senior prom circa 2003.
12. Suit and tie
I love this bucking of gender norms, but Jane needed some better tailoring on this one. It could’ve been Annie Hall chic; instead it’s just ill-fitting menswear.
11. Long burgundy with matching hat
If you take away that odd side flower and the truly terrible hat, this is nothing more than an uninspiring mid-2000s department store find, but the hat turns it into an unforgivable fashion faux pas.
10. Bright yellow
Once your eyes recover from gazing upon the neon yellow color, this dress itself is adorable. I love the playful ruffles, ruched bodice, and accent flower; I just wish it was a slightly softer shade of yellow or a different color entirely. I mean, what was the theme — Tweety Bird cosplay?
9. Olive green
Jane puts this on to demonstrate that some of the dresses are “not that bad,” while Kevin insists this drab olive color is an “instrument of torture inflicted on you by a bride who wants you to look ugly.” They’re both right.
8. Short grey ruffles
This dress is actually pretty cute — it’s one of the few short ones and I like the playfulness of the side bow and the bottom ruffles (though it wouldn’t hurt if they were toned down a little). But this grey color is flattering on approximately 0% of the population.
7. Light blue w/ bolero jacket
This dress feels a bit more “mother of the bride” in fit and cut (look at that early ’90s bolero jacket) than it does bridesmaid, but the color is flattering and screams spring wedding. It ranks in the top 10 merely for being one of the more inoffensive looks here.
6. Purple tulle
This is classic bridesmaid stuff — a pale color somewhere between purple and blue that washes out all of the bridesmaids and perfectly color-coordinates with the floral arrangements. The halter fit is very flattering on Jane, and we’d probably rank this higher if it weren’t for the explosion of purple tulle in the front. The beading accents are pretty and help elevate this dress’ ranking. Bonus points for being the dress that first attracts Kevin Doyle’s eye and for including a sash that is a surprisingly great fashion accessory (see: Casey repurposing it with a tailored men’s shirt for her walk of shame).
5. Wedding dress look-alike
This dress is fairly nondescript and looks flattering on Jane’s figure, but we have to ask — why would a bride choose something so, well, “bridal” for her bridesmaid dresses? It looks more like a wedding dress than a gown that belongs to a member of the wedding party.
4. “L.A.” wedding
To be honest, I don’t hate this look — yes, it’s vastly inappropriate for a wedding, but statuesque Jane rocks both the super-short hemline and the hot pink color. It’s absurd to picture it in a wedding, but as a dress alone, it’s actually pretty cute.
3. Pink sweetheart chiffon
This is a lovely run-of-the-mill bridesmaid dress. With its sweetheart neckline, blend of chiffon and tulle, and bubblegum pink color, it screams “I bought this at David’s Bridal.” Not to mention, Jane just looks adorable in this shade of pink.
2. Pink and gold sari
Honestly, this dress is pretty great — the colors are gorgeous and flattering, and I love the versatility of the draping sari styling. Not to mention, those flats look incredibly comfortable for a long night on your feet. Lastly, though Jane participated in some pretty ridiculous themed weddings, this is a theme that is culturally significant and possesses deeper meaning beyond “I love this movie/aesthetic.” Within that theme, the bride managed to pick a lovely dress with all the vibrancy and sparkle of a traditional Indian wedding. This dress tops the list because of its ability to combine themed apparel with an actually beautiful gown.
1. Jane’s wedding dress
Ok, so this is technically not one of the titular “27,” nor is it a bridesmaid dress, but how could I not put Jane’s wedding dress on the top of my list? It’s stunning and understated — perfect for her character, plus it means I get to celebrate her getting her very own, much-deserved happily-ever-after. I am saying YES to this dress.