Jessica Simpson's Hottest Bikini Photos: Sexiest Swimwear Moments

For Jessica Simpson, being able to wear a bikini is an “emotional” experience. After more than 100-pound weight gains during her three pregnancies, she’s so proud of regaining her bikini body.

On April 7, 2022, Jess shared an Instagram selfie in a tiny pink printed two-piece with the caption, “I have gained and lost 100 lbs 3x so I never thought this moment could or would happen, but I’m finally spring breakin’ wearin’ a BIKINI!!!!!!” She chalked up her success to “”hard work,” “determination” and “self-love” and admitted, “I enjoyed a good proud cry today” over her accomplishment

“I believe in setting small goals for yourself because in my life and how I’ve done it. There’s easy ways to throw in the towel and just feel like it’s impossible,” Jessica revealed during an April 18 appearance on The Real about how she was able to lose more than 100 pounds three separate times. “So, the small goals for me are what helped me achieve the main goal.”

“Being in a bikini was never my main goal. I mean, I did that in my 20s,” she explained. Jess then shared how she didn’t even plan on bringing a bikini along on her family’s mid-April spring break trip to Mexico. “I literally brought bathing suits on that trip without trying on a bikini, because I thought I was just going to be in a one-piece.”

In the end, she decided to give a bikini a try and it fit her to perfection. “When I put that two-piece on, I got super emotional, and I was like, ‘I did this, it happened,'” she recalled. “So, it was just, like, in the moment, and I wanted to share it with everyone because I was very proud of myself for doing what at times felt completely impossible,” about her Instagram bikini selfie.

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Jessica and her husband, Eric Johnson, share three children. Daughter Maxwell was born in 2012, and her little brother, Ace Knute, came along the following year. The entrepreneur showed off her body post-babies in several one-pieces but gradually became more confident with how she looked in a bikini. For her 36th birthday, Jessica shared a photo wearing just a pair of bottoms while topless atop a floatie in her backyard to show off how fine she looked after two children.

The singer had a difficult third pregnancy with daughter Birdie Mae, who arrived in March 2019. While Jessica proudly showed off her 100-pound weight loss the following fall in belted dresses and later skinny jeans, it took her until April 2022 to feel confident enough to rock a bikini once again!

See Jessica’s hottest bikini moments in photos below!