Jennifer Aniston Breaks Fashion Rules Wearing LBD with Unexpected Flip-Flops in NYC Stroll

On August 6, Jennifer Aniston was seen strolling through New York City wearing a little black dress (LBD) paired with an unusual footwear choice: flip-flops. This look highlighted Aniston’s ability to blend sophistication with relaxed style, defying typical fashion expectations by combining a chic slip dress with casual shoes.

Though the black slip dress is often associated with formal occasions, Aniston’s choice to wear simple black flip-flops added a laid-back, ‘90s-inspired edge to her appearance, making the outfit feel effortless and comfortable while still stylish.

Budding Romance and Social Outings in the City

Alongside her distinctive fashion moment, Aniston has been in the spotlight for her new relationship with hypnotherapist Jim Curtis. The couple has been quietly dating for several months after being introduced through a mutual friend, according to multiple sources. Their connection began as friendship and evolved naturally into romance.

Recently, Aniston and Curtis shared a double date with actor Jason Bateman and his wife Amanda Anka, enjoying a three-hour dinner in Manhattan’s West Village. The same group, joined by comedian Amy Schumer, also spent time together last month aboard a yacht in Mallorca, signaling a close-knit social circle.

One insider said,

“They’ve been seeing each other for a few months now. They were introduced by a friend and started out as friends.”

source

About the relationship, the insider added,

Jennifer Aniston
Image of: Jennifer Aniston

“She’s really into self-help and wellness. They are dating, but it’s still casual.”

source

Jim Curtis: A Different Kind of Partner

Jim Curtis is an author, life coach, and hypnotherapist, noted as quite distinct from anyone Aniston has dated before. According to people close to the actress, she is content on her own but open to sharing her life if the connection feels right.

The source described Curtis by stating,

“He is very different from anyone she’s dated before.”

and added,

“She’s been happy on her own, but she’s also open to sharing her life with someone.”

They further explained,

“Jen’s in a very good place right now—grounded, fulfilled, and very happy.”

Personal Growth Amidst a Busy Career

This relationship marks Aniston’s first public romance since her split from Justin Theroux in 2018. Before that, she was famously married to Brad Pitt from 2000 to 2005. Reflecting on recent years, Aniston described a period of intense professional focus combined with efforts to reclaim personal time.

She said,

“a really intensive few years of work,”

and shared candidly,

“I’m a bit of a workaholic, so I’m forcing myself to try to take some time to travel and not work.”

Commitment to The Morning Show Amid Busy Schedule

Currently, Aniston is fully engaged in working on the fourth season of Apple TV+’s The Morning Show, which is set to return on September 17. The actress finds the series demanding, both emotionally and professionally, emphasizing the complexity of the show’s themes compared to her previous iconic role in Friends.

She revealed,

“The Morning Show is just a beast to film. It is layered, it’s complicated, it’s emotional, it hits on a lot of topics and current events, so let’s just say—it’s not Friends.”

As both producer and star, Aniston admitted that the project is draining but rewarding:

“Both producing and starring in a show takes a lot out of you. We’re involved in every single aspect of the show, on top of just the performance side, which is a big piece of it.”

Struggling to Balance Work and Life

Despite her success, Aniston expressed how difficult maintaining balance between professional obligations and personal well-being can be. She acknowledged the importance of this balance but admitted it remains a challenge.

She said,

“It’s so critical, I know, but I’m not good at it.”

Adding,

“Our work is diminishing returns at the end of the day—if you’re just working so much that you don’t have any wonderful life experiences.”

What to Expect Moving Forward

Jennifer Aniston continues to defy conventional expectations both on and off the screen, blending casual style with high-profile engagements. Her relationship with Jim Curtis suggests a grounded and fulfilling personal life, while her dedication to The Morning Show highlights her ongoing commitment to meaningful work.

As the new season premiere approaches, fans can anticipate seeing Aniston tackle complex themes on-screen while maintaining her distinctive personal style—proving that fashion and life choices can reflect individuality and contentment simultaneously.