Two weeks ago, Rihanna finally tapped into the flip-flops trend with snakeskin Amina Muaddi thongs. Fast forward to today: She's already ditched them for transitional fall shoes. Her footwear of choice? Timberland boots.
On August 11, Rihanna's maternity-wear streak returned to Beverly Hills, reportedly to stock up on baby essentials once again. For a late-night shopping trip, the pregnant star styled summer-to-fall staples, starting with Timberlands in the classic light brown shade. Their rubber lug soles just barely peeked out from underneath her oversize dark-wash jeans. From there, the Grammy-winner's baby bump was on full display alongside a cropped bubblegum pink hoodie. It was slightly unzipped to reveal her matching bra, presumably with Savage x Fenty tags.
Rihanna's Timberlands looked so nostalgic with ultra-baggy jeans.
Since she's rarely spotted without a rare designer handbag in tow, I was shocked to see Rihanna's arm noticeably Gucci-free. She left her new Gucci Padlock Shoulder style at home, popping on shield sunglasses and four-figure jewels instead.
Always on board for statement pearls, the Smurfs star wore a tiered choker with a Marie Lichtenberg pendant, plus a Renato Cipullo "R" chain. The $99,900 Audemars Piguet Rose Gold watch, alongside bold diamond bangles, finished the mom-to-be's shopping set.
Rihanna has stood firmly in her sneakers stance this year, only swapping her Puma Speedcats for the occasional pointed-toe pump. As far as I know, she hasn't worn Timberlands since October 2024. Before then, the beloved work boots became a staple during her second pregnancy in 2023. She leaned into their '90s-era nostalgia, pairing them with fur outerwear, cropped polo shirts, and the baggiest of baggy jeans, of course.
In March 2023, the "Lift Me Up Singer" went viral in a striped Loewe shirt and AGOLDE jeans. This time, Rihanna tucked her denim into her Timberlands, which appear to be the same pair, except with bright red laces.
In March 2023, Rihanna revealed her baby bump in a Loewe polo and matching Timberlands.
Before boots season comes ballet flats and loafers weather, but according to Rihanna, Timberlands are an anomaly without an expiration date. They looked just as chic in March 2023 as they did in August 2025. I call it the Rihanna effect.
Shop Boots Inspired by Rihanna
