Jessica Simpson tells PEOPLE that she still loves the de la Renta designs for being "so classy and glamorous"

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Jessica Simpson is reflecting on some of her all-time favorite red carpet looks!

The award-winning singer and fashion industry mogul, 41, tells PEOPLE about five special ensembles she still loves to this day — including three different pieces by the late designer Oscar de la Renta

"I love an Oscar de la Renta moment on the red carpet," she says. "His designs are so classy and glamorous, you immediately feel timeless."

Among Simpson's favorite Oscar de la Renta pieces is the retro, gold-embroidered, tea-length dress she wore in July 2005 to the 13th annual ESPY Awards in Los Angeles. The 1950s-inspired number features a corset-style halter top and full skirt.

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Four months later in November, Simpson stepped out in another Oscar de la Renta outfit at the 10th Annual Accessories Council ACE Awards in New York City. The strapless green-and-white garment perfectly embodied the early 2000s style, with little white flowers and other white accents decorating the dress.

Simpson is also fond of a similar style she wore to the premiere of her 2006 movie Employee of the Month in Los Angeles. The "Irresistible" singer appeared at the event in a red polka dot dress with see-through cap sleeves and a large red belt which added to the sweet, retro vibe of the look.

Simpson's two remaining favorite looks are all about the glitz and glam. The first was the dazzling black dress with gold sparkles that she wore to the VH1 Divas event in April 2004.

jessica simpson
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"This stunning dress was a personal entrance to be remembered," she recalls to PEOPLE. "I brought my very best to the Latin Grammys before taking the stage. I was living an absolute dream of mine since I was a child to perform at a Grammy Awards show. This look is all the feels I was holding."

In November 2004, Simpson flaunted her figure in a sequin black gown featuring a low-cut top held together by delicate strings. The dress was covered in sparkling accents, from the tops of the spaghetti-straps to a bedazzled band at the waistline.

"The dress I wore to VH1 Divas was stunning and I felt magic swirling around me as I was stepping into the world of my voice becoming 'Diva status,' I knew I had to look the part if I was gonna sing the part and the dress didn't disappoint!"

Simpson tells PEOPLE that she has kept some of her favorite styles from past events, and makes sure to take good care of them.

"I have restored pieces of clothing from my storage," she confessed. "It is very hard to dispose of pieces that hold many memories."