Los Angeles, California – October 31, 2025 – As the sun dipped below the Hollywood Hills, casting a golden glow over streets alive with trick-or-treaters and twinkling jack-o’-lanterns, Rihanna Fenty emerged from her sprawling Bel-Air mansion like a vision from a Caribbean fairy tale, her two young sons in tow for what has been hailed as the most heart-melting family Halloween outing of the year. The 37-year-old singer, entrepreneur, and new mom – whose Fenty empire continues to redefine beauty and beyond – traded her usual red-carpet radiance for a whimsical woodland sprite costume, complete with flowing emerald tulle wings that fluttered like fireflies and a crown of autumn leaves woven with tiny LED lights. But it was little Riot Rose Mayers, the couple’s 14-month-old bundle of joy, who truly captivated the night: swaddled in an oversized orange pumpkin onesie, complete with a plush stem hat and embroidered “Boo!” across his chubby tummy, Riot’s gummy-toothed grin and wide-eyed wonder turned every sidewalk into a paparazzi frenzy. “Look at my little gourd – he’s the cutest haunt in town!” Rihanna cooed to a gaggle of neighborhood kids, hoisting Riot onto her hip as A$AP Rocky trailed behind, cradling their elder son RZA in a matching acorn ensemble. In a city synonymous with spectacle, the Fenty-Mayers family’s low-key jaunt through Brentwood’s candy-lit lanes proved that Halloween’s real magic lies not in the glamour, but in the giggles of those who matter most.

The evening kicked off in true Rihanna fashion: a private pre-trick-or-treat bash at their $13.8 million estate, transformed into a pint-sized pumpkin patch wonderland by a team of event wizards from her Fenty creative collective. Towering hay bales sourced from a sustainable farm in Santa Barbara formed a labyrinthine play area, where RZA, the rambunctious 2-year-old with his dad’s signature dimples and mom’s luminous curls, could “hunt” for hidden treats amid faux cornstalks lit by solar-powered lanterns. Riot, still mastering the art of wobbly steps, was the undisputed star of the setup: propped in a custom carved pumpkin throne – a hollowed-out prop foam gourd big enough for his tiny frame, lined with sherpa for ultimate snuggle – he babbled at floating ghost balloons while gnawing on a teething ring shaped like a candy corn. Rihanna, ever the hands-on supermom, orchestrated the chaos with effortless cool: stirring a cauldron of spiced apple cider on an outdoor fire pit, her sprite gown – a bespoke piece from Savage X Fenty’s upcoming holiday line, blending lace-up corsetry with ethereal chiffon – billowing in the breeze as she passed out monogrammed goodie bags filled with organic fruit chews and mini Fenty lip glosses for the older kids.

A$AP Rocky, 37, the Harlem poet-turned-fashion visionary whose AWGE label just dropped a sold-out capsule with Gap, leaned into dad mode with his signature laid-back flair. Dressed as a dapper forest guardian – think velvet cape in deep moss green, antler headpiece forged from recycled metals, and boots scuffed just enough to look lived-in – he scooped up RZA for a piggyback ride through the hay maze, the toddler’s acorn hat (complete with twig antennae and a leaf cape) flopping comically with every bounce. “Rocky’s the king of chill chaos,” a family friend shared, watching as the rapper paused to freestyle a spooky rhyme about “little nuts gathering treats in the night,” drawing peals of laughter from the pint-sized crowd. The couple’s chemistry, forged over a decade of friendship that blossomed into romance amid album drops and red-eye flights, shone through the seasonal silliness: stolen glances over the kids’ heads, Rocky’s hand steady on Ri’s lower back as she bent to tie Riot’s pumpkin booties. Their sons, baptized in Barbados last year in a sun-drenched ceremony blending Bajan rituals with Harlem soul, embodied the best of both worlds – RZA’s boundless energy a nod to Rocky’s stage presence, Riot’s serene curiosity echoing Rihanna’s introspective vibe.

Venturing out into Brentwood’s tree-lined avenues – a neighborhood where mansions hide behind bougainvillea walls and doorsteps groan under artisanal candy hauls – the family became an instant spectacle, though one rooted in relatable joy rather than orchestrated excess. Rihanna led the charge, her woodland sprite ensemble accessorized with glow-in-the-dark vine tattoos that shimmered under streetlamps, a woven basket swinging from her arm overflowing with eco-friendly treats: fair-trade chocolate bars wrapped in leaf motifs and gummy worms dyed with beet juice. Riot, the evening’s breakout heartthrob, rode in a custom Radio Flyer wagon tricked out as a pumpkin carriage – velvet cushions, battery-powered lanterns casting a warm jack-o’-lantern glow, and a canopy of dangling spiderwebs that tickled his toes. His costume, hand-stitched by Rihanna during a late-night sewing session (a skill passed down from her Barbadian grandmother), featured velcro tabs for easy diaper changes and a hidden pocket for his favorite pacifier, shaped like a tiny black bat. “Every stitch is a spell for good dreams,” Ri had posted earlier that day on Instagram, a teaser Reel of her threading the needle while humming a snippet of “Umbrella,” amassing 10 million views before sunset.

As they hit the first block, the Fenty-Mayers magic unfolded in unscripted bursts. RZA, clutching a glow-stick wand that lit up with every swing, dashed from porch to porch, his acorn outfit’s fuzzy tail dragging comically behind him. “Trick or tree-mend-us!” he lisped at a cluster of neighbors – a mash-up of “treat” and “tree” that Rocky claims came from their recent hikes in Griffith Park, where the family bonds over foraging for wild berries. Rihanna, ever the encourager, knelt to his level, whispering, “Remember, mi son, the real treasure’s the sharing.” Riot, content in his wagon throne, drew coos from every doorway: a retired film director slipped him an extra king-size Snickers (“For the future heartbreaker!”), while a yoga instructor mom snapped a quick pic for her feed, captioning it “Pumpkin perfection – RiRi genes hit different.” The rapper dad, antlers casting long shadows, fielded compliments with humble flair: “Nah, it’s all her – queen of the patch,” he’d say, nodding to Rihanna, who beamed back with that megawatt smile that once lit up Super Bowl stages.

Social media, that voracious vampire of the night, feasted on the family’s escapades. Rihanna’s Instagram Stories – a real-time reel of Riot’s pumpkin-pursed lips mid-yawn, RZA mid-candy heist with chocolate smeared across his cheek – racked up 25 million views by 9 p.m., fans flooding with heart-eyes emojis and “family goals” tags. “RiRi serving spooky slay while keeping it cozy – motherhood unlocked,” gushed one viral comment from Lizzo, who crashed a nearby block party in a glittering witch getup. A$AP Rocky contributed to the digital deluge with a low-key TikTok: a slow-mo of him and RZA “acorn-rolling” down a gentle hill (safely padded with hay), set to a remixed “F**kin’ Problems” with eerie theremin overlays, hitting 15 million likes. Even the littlest star shone online: a fan-edited montage of Riot’s wagon parade, synced to Rihanna’s “Diamonds” acoustic version, trended under #RiotTheGourd, spawning thousands of copycat costumes overnight on Etsy.

But beyond the buzz, this Halloween etched deeper grooves in the Fenty-Mayers lore – a chapter of normalcy in lives defined by diamond-crusted spotlights and boardroom battles. Rihanna, whose Clara Lionel Foundation just pledged $5 million to Caribbean climate resilience post-Hurricane Melissa, sees these nights as sacred resets: “In the rush of releases and runways, this – candy corn crumbs and kid chaos – recharges my roots.” Rocky, fresh off his directorial debut at the Toronto Film Festival (a gritty coming-of-age tale drawing from his foster-care youth), echoed the sentiment in a rare E! aside: “Halloween’s our equalizer – no scripts, just spooks and snuggles.” For the boys, it’s pure enchantment: RZA, already a budding artist with crayon murals of “pumpkin monsters” adorning their nursery walls, declared the night “best ever” after scoring a full-size Kit Kat; Riot, oblivious to the adoration, simply burbled contentedly, his pumpkin hood slipping over one eye like a mischievous mask.

As the clock neared curfew – the family’s self-imposed 10 p.m. pumpkin-hour for little ones – the quartet looped back home, wagon wheels crunching over fallen leaves. Rihanna scooped Riot into a rocker on the veranda, his onesie unzipped to reveal chubby toes wiggling in the chill, while Rocky and RZA sorted their haul on a picnic blanket: Twix for trading, Reese’s for rationing. Fireflies (courtesy of eco-lanterns) danced overhead, the air sweet with caramel and contentment. In a world where Rih’s every move mints headlines – from Fenty Skin’s holiday drops to whispers of a long-awaited ninth album – this Halloween was her quiet anthem: family as the ultimate flex. With Riot’s pumpkin hat dangling from a porch swing like a talisman, the night whispered a truth as timeless as her hits: the scariest monsters are the ones we outgrow together, but the sweetest treats? Those shared under the harvest moon, one adorable gourd at a time.