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Caitlyn Jenner flashes a hint of cleavage in plunging black dress after keeping it chic in denim jeans and stylish blouse as she steps out in New York City

Published: 15:13 EST, 10 February 2016 | Updated: 05:59 EST, 11 February 2016

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She has been experimenting with different styles over the past few months, so it’s no wonder Caitlyn Jenner made sure to stand out during New York Fashion Week.

The 66-year-old reality star kept it chic in denim jeans and a plunging blouse, before slipping into a pretty black dress and smart heels as she headed to a meeting on Wednesday.

The mid-length frock fell just over the knee but offered a plunging neckline for a hint of cleavage.

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Looking the business: Caitlyn Jenner worked two stylish looks as she stepped out in New York on Wednesday

A frill trim with white piping accentuated her waist and she added a matching blazer for a coordinated look.

Caitlyn carried a classic black handbag to complete the look and wore her favourite nameplate necklace.

Earlier in the day the I Am Cait star was pictured grabbing a coffee from the Starbucks opposite her hotel, Trump Soho.

Just a hint! The 66-year-old star flashed a little cleavage in a pretty black dress with white piping when she headed to a meeting

Sophisticated chic: Caitlyn added a white blazer to tie together her look

Caitlyn was pictured ordering from baristas before putting on a leggy display in her knee-high boots over skinny jeans.

Her look was kept quite casual with a lace-up knitted sweater and she layered a long dark coat over the top.

She wore her auburn locks loose in tumbling curls and covered up in stylish sunglasses.

Meanwhile, the former Olympian caught up with ex-wife Kris, 60, with dinner Hunt & Fish Club on Tuesday night.

Caffeine fix: Jenner stepped out of her hotel earlier that day to get a Starbucks from across the street

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Thanks-a-latte! Luckily for the 66-year-old there was a store directly across from the Trump Soho hotel and the star was pictured grabbing a coffee to go

Well heeled: Caitlyn looked stylish in skinny jeans and boots with a long dark coat

The duo were pictured arriving at the eatery along with Kris' toyboy Corey Gamble, 35.

The meet-up came after the mother-of-six opened up to Harper's Bazaar about how she felt as her ex-husband Bruce Jenner publicly made his transition into living as a woman after their divorce in 2015.

She revealed she had a hard time accepting Caitlyn at first after 22 years of marriage.

'I think at some point, although it was difficult and, uh, a challenge… I just have to let it go. And try to be tolerant,' she told the magazine. '[With] prayer. God. You know, just trying to understand. It takes time.

Waiting fans: Caitlyn wore her auburn locks loose in tumbling curls and covered up in stylish sunglasses

These boots are made for walking: The TV star has a busy week ahead of Fashion Week events

'But time is a wonderful healer. And we have two children together. It’s important for my kids to see our family strong and united,' she concluded.

The KUWTK star also revealed that she was unaware of what the term transgender meant, and the revelation left her doubting the validity of their marriage.

'Thank God, I never doubted myself,' she said. 'I never really doubted my femininity. I just doubted the relationship. You know, what were those 20-plus years all about?'