Lourdes Leon looked prim in proper in a dark gray coat, navy skirt, and mary jane-style shoes while accompanying her mother to the Versace AT The V&A Party in 2002.
While spending the day at the park with her family in 2003, Leon was adorable in a long sleeved pink Juicy Couture t-shirt, midi-length denim skirt, pink flower sandals and a coordinating top and headband.
In 2004, Madonna and Lourdes wore coordinating flared jeans to the park.
In 2005, Lourdes Leon wore a cute denim-on-denim ensemble paired with black leather boots and a silver chain belt.
In 2005, nine-year-old Leon attended the "Harry Potter and the Goblet of Fire" premiere in a double-breasted black coat with white accents and a sparkling pink mini handbag.
In 2006, Leon wore a bright turquoise t-shirt, denim capri pants, and a pair of wedge heels for an outing with her mother.
At a 2008 Malawi Benefit in NYC, Madonna and Lourdes both wore simple, chic dresses. While Madonna wore a nude cowl-neck Gucci dress, Lourdes looked darling and modest in a black silk midi dress that she paired with black tights.
Lourdes looked like an emerging pop star on the red carpet at the premiere of "Nine" in 2009, wearing a lace mini dress with Dr. Martens, a black leather jacket, motorcycle gloves and fishnet tights.
In 2010, Leon attended the launch of Macy’s ‘Material Girl’ collection in ripped tights, a mini dress, studded leather jacket, and plaid shirt.
Lourdes Leon looked confident on the red carpet at the 2011 Vanity Fair Oscar Party in an AllSaints Aztec print mini dress with black platform pumps and lots of arm candy.
Celebrating Macy's Material Girls collection with Kelly Osbourne in 2011, Lourdes Leon wore a playful yellow dress with black platform pumps.
In Ibiza in 2014, Lourdes Leon hit the beach in a grey tank top, mini skirt, sneakers and bright red sunglasses.