Rihanna has never followed fashion rules, she rewrites them. As she turns 38, you can look back and see how each era marked a shift in style, confidence, and culture. From red carpets to grocery runs, she has proven that every appearance can be a moment.
Here are nine looks that helped define her legacy.
1. Diamond Ball drama in 2017
At her third annual Clara Lionel Foundation Diamond Ball in 2017, Rihanna chose Ralph & Russo couture. The black gown featured a dramatic high-low hem, a structured bodice, and a sweeping train. Chopard diamonds framed her neckline and completed the look.
Rihanna brings dramatic elegance to the Diamond Ball in a black couture gown with a sweeping train and statement diamonds.
(Getty Images)
This was not just a red carpet appearance, it was a statement. She showed how to balance elegance with edge, keeping the silhouette classic but the energy modern. It set the tone for her future as both a fashion leader and a philanthropist.
2. Leopard power in 2019
In October 2019, Rihanna stepped out in New York wearing Saint Laurent by Anthony Vaccarello. The one-shoulder leopard dress was paired with tall burgundy boots and a Dior handbag. It felt bold, confident, and effortless.
Rihanna steps out in a bold leopard one-shoulder dress paired with tall boots for a confident fall look.
(Getty Images)
If you want to recreate this vibe, start with a one-shoulder animal print dress in a midi length. Pair it with knee-high or over-the-knee boots in a deep shade like burgundy or chocolate brown.
Keep accessories sleek and structured, such as a small top-handle bag and narrow sunglasses.
3. Orange takeover in 2020
Spotted in New York in February 2020, Rihanna embraced a head-to-toe orange look. She wore a mini dress with a matching trench coat and creamy gold slouch boots. The monochrome styling made the outfit stand out.
Rihanna commands attention in a head-to-toe orange ensemble layered with a matching coat and metallic boots.
(Getty Images)
To try a similar look, choose one strong color and build around it. A knit mini dress layered under a matching coat creates a clean silhouette.
Finish with neutral boots in beige, cream, or soft gold to balance the brightness.
4. Grocery run, but make it fashion in 2021
In March 2021, Rihanna went grocery shopping in an open Hawaiian shirt and a denim mini skirt. She added Amina Muaddi heels and bold sunglasses. The result felt relaxed but intentional.
Rihanna proves even a supermarket trip can double as a style moment with heels and bold layers.
(Rachpoot/MEGA//Getty Images)
Even during an errand, she refused to look ordinary. The mix of casual pieces with statement heels showed her playful side. It proved that style does not depend on the setting.
5. Sheer confidence in 2021
In Los Angeles in August 2021, she stepped out for dinner in a sheer, bedazzled slip dress. Layers of glittering necklaces, silver heels, and a matching handbag added shine. The outfit was simple in shape but striking in effect.
Rihanna steps out in a shimmering slip dress layered with bold jewelry for a sleek dinner look.
(Diggzy/Shutterstock//Shutterstock)
For a similar evening look, choose a slip dress with subtle shimmer or crystal details. Layer delicate chains of different lengths to create depth without overwhelming the outfit.
Complete it with metallic heels and a compact clutch to keep the focus on the dress.
6. Super Bowl press moment in 2023
Ahead of her Super Bowl LVII Halftime Show performance, Rihanna attended a press conference in full SS23 Alaïa. The ensemble included an oversized leather jacket and a snake print dress. The silhouette was strong and modern.
Rihanna teases her halftime show return in a sculptural leather jacket and snake print dress.
(Kevin Mazur//Getty Images)
The look built anticipation for her return to the stage. It felt polished but not overdone. You could sense that she understood the power of timing and presentation.
7. Paris couture cool in 2024
At the Dior Haute Couture show in January 2024, she wore head-to-toe Dior. The oversized black puffer coat, matching midi dress, leather gloves, and baseball cap created a layered look. White pointed heels and a structured Lady Dior bag added contrast.
Rihanna mixes sporty and couture in a layered all-black Dior look at Paris Fashion Week.
(Dave Benett//Getty Images)
This outfit mixed sporty and couture in one frame. She showed that high fashion does not need to feel stiff. It was relaxed, but still precise.
8. Dinner in Los Angeles in 2024
In April 2024, she was seen leaving Giorgio Baldi in a metallic champagne coat. Underneath, she wore a graphic tee and loose jeans. Pearls, a Dior Saddle bag, and white pointed Gucci heels elevated the outfit.
Rihanna upgrades casual denim with a dramatic metallic coat and layered pearl accessories.
(The Hollywood Curtain/Bauer-Griffin//Getty Images)
The mix of casual denim with a structured coat captured her signature balance. She made everyday staples look intentional. It felt effortless, but carefully styled.
9. FENTY x PUMA in London in 2024
At the FENTY x PUMA Creeper Phatty Earth Tone launch party, Rihanna embraced oversized tailoring. She wore a moss green jacket over a brown jumpsuit and paired it with earth-toned creepers. Yellow aviator sunglasses and layered gold chains completed the look.
Rihanna embraces oversized tailoring and earthy tones at her FENTY x PUMA launch event in London.
(Neil Mockford//Getty Images)
This moment reflected her role as a business mogul. She was not just wearing fashion, she was building it. The outfit felt grounded, confident, and fully her.
Final thoughts
Rihanna at 38 is not just a singer or entrepreneur, she is a style blueprint. Each of these moments shows how she blends risk with ease. When you look back, you see more than outfits, you see influence.