The Best, Weirdest, and Most Outrageous Victoria's Secret Fashion Show Moments Ever

In honor of the show's 20th anniversary.

image
Getty Images

This year marks the 20th anniversary of the Victoria's Secret Fashion Show. For two decades, models like Tyra Banks, Heidi Klum, Gisele Bündchen, Naomi Campbell, Adriana Lima, and Karlie Kloss have been parading down the VS runway in everything from full, furry Angel wings to itty bitty million dollar bras, while big-time performers like Kanye West and the Spice Girls serenade them. Here, 65 of the best, craziest, and most memorable moments in Victoria's Secret history.

1 of 58
Gail Elliott, 1995

The very first Victoria's Secret Fashion Show took place at the Plaza Hotel.

2 of 58
Angelika Kallio, 1995

And they made fashion statements from the get-go: sunglasses inside! Boots with undies!

3 of 58
Stephanie Seymour, 1996

Sexy bridal wear!

4 of 58
Naomi Campbell, 1996

Naomi made her VS debut on the 1996 runway.

5 of 58
Rebecca Romijn, 1997

Did you know Rebecca Romijn was a regular on the early VS runways?

6 of 58
Naomi Campbell, 1997

Naomi channeled a boxer in this not-so-practical bra (and robe!).

7 of 58
Tyra Banks, 1997

Tyra made her Angel debut on the runway in 1997.

8 of 58
Georgianna Robertson, 1997

Nothing says "Happy Valentine's Day" like, well, like that.

9 of 58
Tyra Banks, 1998

Tyra was one of the models to wear the very first set of Angel wings during the 1998 show.

10 of 58
Gisele Bündchen, 2000

She is like the most fantastic golden phoenix.

11 of 58
Gisele Bündchen, 2000

For the 2000 show, Victoria's Secret took the production to Cannes.

12 of 58
Heidi Klum, 2001

Heidi Klum wore the first-ever fantasy bra on a Victoria's Secret runway: "The Heavenly Star Bra", worth $12.5 million.

13 of 58
Alek Wek, 2001

It's like a heart hot plate for your hoo-ha!

14 of 58
Karolina Kurkova, 2001

What Santa really looks like under that beard.

15 of 58
Angelic Ambience, 2001

Because, okay?

16 of 58
Peta Protesters and Gisele Bündchen, 2002

Surprise!

17 of 58
2002

Seriously, how would someone even put this on?

18 of 58
Naomi Campbell, 2002

Naomi, the original firebird!

19 of 58
Destiny's Child, 2002

Oh what we wouldn't give to have been at this Destiny's Child performance.

20 of 58
Ana Beatriz, 2002

Before models went through the full body-buff-spray-tan-glow process they do now, Ana Beatriz walked the runway modeling some very visible tan lines.

21 of 58
Karolina Kurkova, 2002

Like the most gorgeous avant garde Big Bird.

22 of 58
Tyra Banks, 2002

Tyra snagged her lingerie train on something as she stepped onto the runway. Which is one argument for not wearing a lingerie train.

23 of 58
Sting, 2003

Moves like Jagger.

24 of 58
Heidi Klum, 2003

Heidi walked the runway in some of the hugest angel wings ever.

25 of 58
Karolina Kurkova,Gisele Bündchen, and Alessandra Ambrosio, 2005

Karolina, Gisele, and Alessandra doing their best Mean Girls impression.

26 of 58
Gisele Bündchen, 2005

Gisele holds the record for modeling the most expensive fantasy bra ever: the $15 million "Red Hot Fantasy Bra" in 2000, which featured even more bling than this spicy red number she sported in 2005.

27 of 58
Heidi Klum and Seal, 2005

Sexy LED undies and kisses on the runway.

28 of 58
Sexy Army, 2005

Because this is a totally practical soldier uniform.

29 of 58
Miranda Kerr, 2006

Miranda, the sexy snow bunny, made her VS runway debut in 2006 and later replaced Gisele as an Angel in 2007.

30 of 58
Doutzen Kroes, 2006

Sexy college graduate?

Advertisement - Continue Reading Below
More From Fashion