Supreme seal of approval! Ashlee Simpson rubs shoulders with her boyfriend Evan's superstar mom Diana Ross

PUBLISHED: 09:29 EST, 16 October 2013 | UPDATED: 10:02 EST, 16 October 2013

View
comments

The stars came out for the premiere of the highly-anticipated movie Crazy Sexy Cool: The TLC Story in New York City on Tuesday night, but none shone brighter than music legend Diana Ross.

It was a decidedly family affair as the Ain't No Mountain Higher songstress proudly supported son Evan Ross, who stars in the film as the popular '90s girl group's record producer and bandmember Rozonda 'Chilli' Thomas's baby daddy, Dallas Austin.

The 25-year-old actor and musician was also joined by his ever-present girlfriend of several months, Ashlee Simpson, and half-sister Rhonda Ross Kendrick at the event held at AMC Loews Lincoln Square.

Lucky man! Evan Ross was flanked by three lovely ladies - sister Rhonda Ross Kendrick, mom Diana Ross and girlfriend Ashlee Simpson (from left) - at the New York premiere of Crazy Sexy Cool: The TLC Story on Tuesday

Mom-of-one Ashlee looked chic as she snuggled up close to her man, with whom she has become inseparable since taking their relationship public in July this year.

The 29-year-old donned black dress pants, a fun black and white polka-dot top, a black leather jacket and standout red stilettos with black toe detail.

More...

Crazy Sexy and double Cool: TLC's T-Boz and Chilli pose on the red carpet with actresses playing singers in new biopic

The pretty blonde wore her hair back in a simple low ponytail, with tendrils framing her face, and looked glam with her subtle yet striking eye make-up and ruby red lips.

In stark contrast, her beau seemingly made no effort for his big premiere, dressed in his staples of baggy black pants, scruffy old combat boots, a white v-neck tee that was held together with a safety pin and a black jacket with silk lapel and gold shoulder detail.

Outshone at his own event: While the women in his life made an effort to dress up for the prestigious event, the 25-year-old looked decidedly dishevelled in his signature scruffy attire

His mom, who has certainly developed her own signature style over the years, stood out in her soft bubblegum pink blazer, which she matched to her fun pink divalicious sunglasses.

The 69-year-old kept the rest of her ensemble simple, wearing black leggings, a top and cute ballet flats.

The mom-of-five looked proud as punch on the arm of her lookalike youngest son and eldest daughter, Rhonda, who has also inherited her famous mother's talent as a singer-songwriter.

The 42-year-old wore cuffed jeans, fun lace-up black boots, a black long-sleeved T-shirt and a fur-trimmed denim waistcoat, while she carried a gold clutch that matched her huge hoop earrings and cuff.

Going strong: The 29-year-old mom-of-one has been inseparable from her beau since taking their relationship public in July, seen here together enjoying a day out in Malibu on Monday

Though her best accessory of all was her megawatt smile, which she couldn't wipe off her face.

She later took to Twitter to sing the praises of both the film and her brother's role in it.

'@TheRealTBOZ Generous of U 2 share your seats with us! Thnx! #crazysexycool is FANTASTIC! @realevanross is great as @DALLASAUSTIN Congrats!'