9 Fall Outfit Ideas To Try THIS Weekend

Photographed by Christelle de Castro
It's easy to argue that fall weekends are the best weekends — after all, what other time of year can you enjoy apple-picking, fireside brunches, and a live source of street-style inspiration (courtesy of Fashion Month)? But, as fashion folk, there's no denying that what we love most about this delightful three-month stretch is the excuse to cloak ourselves in oversized sweaters, cocoon-like coats, up-to-there boots, and every cozy-cool piece in between.
So, we brought three talented, sartorial stars together for the ultimate weekend in NYC — and talked fall fashion. Meet up-and-coming model Betty Adewole, who's graced the runways for Alexander McQueen, Tom Ford, and Stella McCartney; Iranian-American photographer Sunny Shokrae, whose intimate portraits and editorials have made her an R29 favorite; and singer-songwriter Diane Birch, whose pop-inflected grooves have hooked the likes of Prince and Questlove. To put it simply, these ladies are killing it — and so is their ever-evolving style.
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Ahead, check out this power trio's adventures about town and their fall-perfect looks, featuring their favorite pieces from Coach's latest collection. Is it the weekend yet?
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Photographed by Christelle de Castro.
French Toast Feast

Model Betty Adewole (left), photographer Sunny Shokrae (middle), and singer-songwriter Diane Birch (right) kick off their weekend with a low-key patio brunch.

Betty: Augden cable knit sweater, Lady Grey hoop earrings and cuff, and Ètudes hat; Sunny: vintage T-shirt and Lady Grey silver drop earrings; Diane: Lady Grey cuffs.
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Photographed by Christelle de Castro.
Diane's Style Weapon: Cheeky Sweater
"I love the playfulness of this sweater," Diane says of her cheeky graphic knit. "I like to wear my boyfriend's clothes, so this outfit, with the loafery-type shoes, is an extension of that but better-fitting!"

Her Style Evolution
The 30-year-old chanteuse had developed her tomboyish style by the time she met Prince — who invited her to jam with his band after hearing her play in a Beverly Hills hotel in 2006. But, before she came into her own, she went through a few sartorial phases."I was 15 when I got my first gig, playing at this lunch place in Portland, Oregon; I would roll in with a Marie Antoinette outfit on. Then, when I moved to L.A., I wanted to be professional and would wear business suits and stilettos. I had a blowout — the whole thing."

Diane: Ètudes black hat and her own jeans.
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Photographed by Christelle de Castro
Betty's Style Weapon: Suede Mini
Confession: Betty had never really thought about wearing a suede miniskirt before donning one for her Saturday morning rendezvous with Sunny and Diane. But, she's not adverse to the look. "I like the grommets," says the 22-year-old face of Tom Ford Beauty. She's already dreaming up outfits with her gold Dr. Martens.

Her Style Evolution
Before she was discovered at 17, while shopping with her mom at a mall in East London, the former athlete lived in trainers, track suits, boyfriend shorts, and caps. "I had no idea about fashion," says Betty of her childhood. "But, I remember my mom had these two silk designer shirts she wore for special occasions. I didn't know what they were at the time, but I knew they were really important. One was cream and had a small, black print all over. The other was black and had a multicolored print, like red, pink, and green."
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Photographed by Christelle de Castro.
Sunny's Style Weapon: Vintage Band Tee
"When I meet my friends for brunch, I usually just show up in my tennis clothes," says the photographer. Though, when she has time to change, she'll throw on a vintage band tee. "When I moved to New York, I ditched a lot of my vintage stuff, but I held onto my old band T-shirts. They're so...forever classic."

Her Style Evolution
"I was really into punk rock and had half a million band T-shirts," says Sunny, who grew up in Southern California after her family left Iran during the Cultural Revolution. "I was really into vintage clothing, and my mother always yelled at me for getting secondhand stuff. It's like everyone's rebellious teenage story."

Sunny: Risto leather pants, Lady Grey ring, and Topshop sunglasses.
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Photographed by Christelle de Castro
After loading up on a healthy B-fast spread, the trio kicks back with a side of herbal tea.

Betty: AGL Chelsea boots.
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Photographed by Christelle de Castro.
Pre-Cocktails Chill Sesh

Before heading out for drinks, Sunny, Diane, and Betty start the night in the best way possible: leisurely hanging at a friend's epic downtown apartment.

Sunny: Vince Camuto button-down, Mega Mega jewelry, and her own gold bangles; Diane: Coach sleeveless sweater, AGL leopard lace-ups, Mega Mega jewelry, and her own vintage gold pants.
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Photographed by Christelle de Castro.
Betty's Style Weapon: Modern White Button-Down
Betty's going-out uniform usually includes jeans and a crisp shirt, which she sports at her friends' music gigs. "One of my best mates is in a band, and a few of my friends DJ — mostly electro music. I also like bars or pubs; you can wear what you want."

How She Makes It Her Own
"I might wear a belt with it and add a necklace. I might make some holes in my jeans or add some badges."

Betty: Coach shoes, Topshop distressed jeans, and Mega Mega jewelry; Sunny: Vince slip-on shoes.
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Photographed by Christelle de Castro.
Diane's Style Weapon: Vintage Palazzo Pant
"I wear a lot of men's suits to perform — like a cross between Charlie Chaplin and Patti Smith. I recently wore these gold pleated pants. They're good performing pants because the fabric is really nice and they're a bit glammy."

How She Makes It Her Own
"I like the idea of wearing them with something that's simple but a heavier texture — like this sleeveless sweater — or more casual like a T-shirt...something that's a little bit unexpected."
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Photographed by Christelle de Castro.
Sunny's Style Weapon: Bold Mini
"When I host parties, I like wearing that dress in my closet that I never wear or wearing a structured skirt. I think it's really important to always look polished, no matter what you're wearing."

How She Makes It Her Own
"I like the balance of having something more casual with something structured and polished — like this red skirt and button-down is just so perfect with a pair of casual slip-on shoes or sneakers. It would have looked so weird with a pair of heels — it's just not me."
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Photographed by Christelle de Castro.
Almost time to head out, the girls make their way to the mirror. Betty decides to go bold and barefaced. "My style has definitely changed since I cut my hair earlier this year," she says. "With hair, you have that to hide behind. So, the cut made me more confident. I’ll wear my face and that’s it. It’s made my style more boyish, but I also dress cleaner and neater with short hair."
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Photographed by Christelle de Castro.
Sunday Afternoon Strut

On the docket for day two: a stroll through NYC's West Village in their Sunday best — statement outerwear and next-level layering.

Sunny: Risto black leather pants; Betty: Coach jacket and skirt, and Negri Firman gold sparkle baseball cap; Diane: Coach bag and AGL brogues.
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Photographed by Christelle de Castro
Betty's Style Weapon: The Cold-Weather High-Top
"Since I started modeling, I've been exposed to so many different styles and designers," says Betty. "But, I still love my sneakers!"

Her Fall Style Crush
Besides her sneakers, Betty has also clung onto her trusty caps from her days as an avid skateboarder, which have transitioned well into her new model-off-duty style. "It’s an easy accessory to wear," she says. "I have a solid one that goes with everything. It saves me time; I don’t have to worry about my hair."

Betty: Coach Rhyder Messenger Bag.
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Photographed by Christelle de Castro
Diane's Style Weapon: Boxy Moto
"I love coats and jackets. They're my favorite pieces of clothing to wear," says Diane. "I've collected so many leather jackets over the years, trying to find that perfectly beat up one. I think you have to run it over with a truck a few times to get that worn-in look."

Her Fall Style Crush
"I'm feeling belts right now. The last year or so I've been into this really gaudy, vintage gold belt — it must be from the '80s — this crazy baroque gold-and-black chain belt."

Diane: vintage ABBA T-shirt.
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Photographed by Christelle de Castro
Sunny's Style Weapon: Statement Topper
"That jacket was amazing," says Sunny about the red-and-black houndstooth coat she wore for her brisk fall stroll. "It reminded me of this vintage jacket I have. It's striped, and it's really warm and cozy. I love trench coats, too — utilitarian trenches that are really menswear-y."

Her Fall Style Crush
"My old tees have a lot of nostalgia for me, but they're also timeless. You can wear them with jeans; you can wear them with something dressier, like these leather leggings and booties; you can wear them with shorts. You can wear them to bed; you can wear them to the grocery store. They make everything look instantly cool. They're just so versatile."

Sunny: Topshop sunglasses.
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Photographed by Christelle de Castro
Fun NYC fact: Charming sidewalk benches are a city shopper's dream.
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Photographed by Christelle de Castro
Sunny throws us an over-the-shoulder glance as the crew heads home, and reflects on her eclectic weekend style: "I wear whatever I want, wherever I want. One day it's neutrals, the next it's menswear. That's what makes getting dressed so fun."
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