Lily Aldrin, played by the lovely Alyson Hannigan, was one of the five main faces of the television show How I Met Your Mother, arguably the longest love story in recorded history. We were blessed with getting to watch the fiery redhead for nine seasons as she weaved in-and-out of her best friend’s romantic tale, and most of the time, she looked incredible doing it.
While Hannigan got to wear some beautiful clothing on How I Met Your Mother, she was also able to pull off some of the worst outfits that the show could dress her up in.
Worst- Goth Lily
Remember the seemingly sweet and rather innocent goth version of Lily from the earlier seasons? The one who acted as though she knew that her soul wasn’t as black as her hair and that she was just exploring her horizons as a wild-and-free teenager? Yeah, we want her back immediately.
The later seasons often had Hannigan flashing-back to her adolescent years (much like the earlier seasons did) but changed her look up dramatically from a wannabe grunge-girl to what seemed like Kurt Cobain’s evil twin. Everyone tends to regret how they looked in high school, but Lily was far from her prime.
Best- Red Dress Lily
Speaking of her prime, it didn’t get a whole lot better than when Lily strolled into the Museum of Natural History looking gorgeous enough to make the mummy’s turn their heads. In the season 6 episode, “Natural History,” our favorite kindergarten teacher wants desperately to hold onto who she was in high-school/college and refuse to admit that she has grown up from being that person, but her outfit couldn’t say differently.
She swapped out the red-flannel of her youth for a stunning red dress instead and couldn’t have looked more grown-up, and nobody was complaining. Galactic-President-Superstar-McAwesomevillve approved!
Worst- Moose-Sweater Lily
To be fair, pleasing your in-laws is never an easy task. But Lily had an Eriksen sized bar to clear when she visited Marshall’s mother. There aren’t two souls on earth who could’ve pulled off the atrocious duel-sweater given to the world’s cutest couple because the world’s cutest couple couldn’t even pull it off!
Marshall and Lily are notoriously adorable, but there’s something so sickeningly sweet about sharing an article of clothing that it’s hard to stomach, like a rich piece of chocolate mousse cake (hold for applause.) This was easily one of Lily’s worst looks, and it didn’t even make Judy happy. Just throw on a Vikings jersey, Lily, you’ll be fine.
Best- Baby-Making Lily
To be clear, there were several “baby-making” outfits that Lily donned throughout the series, and every one of them was better than the last, so feel free to binge-watch the entire series and pick your favorite. But the first one in the Season 4 episode, “Not a Father’s Day,” was particularly nice as it was the first time we got to see our favorite sitcom couple take their first step into parenthood.
Granted, the step they took was barely a baby-sized one, but admitting whether you are or aren’t ready to have children is part of the being-a-parent process. Luckily for the audience, they didn’t start making children, so we got to see Lily in a few other outfits that should’ve been for Marshall’s eyes only.
Worst- White-Whale Lily
Wow. Just wow. Was there anything about the series they didn’t try to ruin in the finale? There are over two-hundred episodes of How I Met Your Mother, and finding five outfits where Lily looked unflattering was a genuine challenge, but this fish was dead in the water before it even grew fins.
Lily’s “white-whale” Halloween costume was, unfortunately, one of the most memorable moments of the series finale as it was followed by a heart-breaking conversation between her and Robin (again, ruined everything.) And if that weren’t enough, how ridiculous Lily looks in the costume completely takes away from the seriousness of the moment. This was bad. High-school, literary magazine bad (High-5 if you got the season 1 reference.)
Best- Parrot Lily
While her season 9 Halloween costume might have been horrendous, Lily’s season 1 Halloween costume officially confirmed that she was the coolest girl in the How I Met Your Mother universe, and it didn’t stop there. Lily’s hall-of-fame line-up of Halloween costumes included R2-D2, a pepper shaker, Dr. Frankenstein, and even Michael Cera, but none of them came close to the tropical parrot.
Her obsession with dressing the best may have led to her accumulating a debt the size of Mount Waddington (are we saying that right, Robin?) but it also led to a $50 gift certificate at Maclaren’s Pub and that should buy at least a couple of rounds for the gang.
Worst- Bridesmaid Lily
Traditionally speaking the bridesmaids are supposed to wear a flattering dress in a hideous color in order to not draw attention away from the bride; no problem with that. But making Lily suffer through this outfit for 5 seasons?! That was just cruel. This dress looked like it should have been wrapped in a Bazooka Joe comic. And again, she had to wear it for at least one episode for five seasons!
Not to mention that one of Lily’s best qualities is her natural red-hair, which clashed with the pink and was pinned to the back of her head in a bun. The worst part is that Lily had another horrible outfit that was almost identical to this one when she was a bridesmaid at Punchy’s wedding! Luckily she was able to break the curse at Ted and Tracy’s wedding, but we all know that that was just a little ways down the road.
Best- Bride Lily
Wow. Just wow. And yes, those are two completely different “wow’s” than the ones we gave for “white-whale Lily” because Alyson Hannigan has never looked more stunning than she did on her make-believe wedding day (and not the one in the boat off the coast of Atlantic City). Pinpointing every aspect of her flawless outfit would be redundant because while she may not have felt like a princess, she certainly looked like one.
Despite not wearing her “Property of Marshall” panties, this two-episode outfit was angelic and solidified every fan’s ever-lasting crush on Lily-pad. She probably looks just as amazing in her “Lily & Marshall: Rockin it since 96” sweatshirt.
Worst- Stripper Lily
Of all the possible doppelganger persona’s the gang could have been portrayed as, a stripper Lily was beyond anyone’s wildest dreams (that was before the doppelganger story-line even existed), and they chose to butcher it! The hair, the accent, the mole! Even Barney, a man with as much mojo as Austin Powers, shouldn’t have been able to take his eyes off that thing.
Technically Russian stripper Jasmine wasn’t actually Lily, so all can be forgiven. Lily was no prude when it came to her sexual desires during the show, and whoever botched this missed opportunity deserves a New-Marshall sized beating.
Best- “Naked Man” Lily
Time to floss, Marshall. It turns out that while Lily Aldrin might have a closet full of designer clothes and expensive Halloween costumes, ultimately, her best outfit is her - wait for it - birthday suit. How I Met Your Mother fans will never forget the season 4 episode, “The Naked Man,” or rather woman in this instance, when Lily used her 49th reason for ‘doing-it’ on Marshall and, as he so eloquently stated, “nailed it.”
Wearing nothing more than a ponytail, a necklace, and a smile, the real kicker behind this outfit was that it showed how sensual Lily actually was. Do your thing, Miss Aldrin. Bet it works more than two out of three times on Marshall, guaranteed.
