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This girl is the receptionist at my work. She has this sort of  neo-punk personality: friendly, but doesn’t give too much of a shit. She pretty much wears the same outfit everyday - all black, short skirt, high heels - and commutes via this beater pink bike, usually while smoking a cigarette. I see her more riding on the streets than I do at the office, and always wanted to take her portrait. 
Points for juxtaposition of black heels and duct tape on bike frame; leather rocker skirt.
Bonus points for the matching pink chain.
Style rider on 6th ave. 

Good lord where do I even start? First he told me about the bike. “It’s a martonecyclingco. Designed by Lorenzo Martone, who used to be the boyfriend of Marc Jacobs. Made out of sustainable materials, and the defining design is each one has a red chain.”
Bonus points for his matching hat, which was red leather with a gold bear; his bag, which was Louis Vuitton; his helmet, which is also Martone. Jackpot!!  
Style rider on North 6th. 

Can I take your picture?
(He kind of just stared at me for about a minute, as demonstrated in the gif. Admittedly, I was a little nervous. Then he took off suddenly, and I followed him.)
Where did you get your hat?
"Back there. On the street. Where I find everything."
(He then took a right and disappeared.)
Bonus points for his jeans - on the back, where the logo normally goes on the upper right butt, he had written “FUCK BUSH”. 
Style rider on Grand st.

Where’d you get that dress?
"Gap, if you can believe it."
I thought their tagline was ‘Dress Normal’?
"Well, this was from last season."
Points for being hilarious through the whole ride; ushering in the prep look to formerly grungy Williamsburg.
Style rider on Kent ave.

"This blazer belonged to my grandfather."
Points for somehow, consciously or unconsciously, matching blazer, shoes, glasses, hair and bike box; great bike (sorry, forgot the brand).
Bonus points for great smile and overall neo-preppy style.
Style rider on North 5th street.
Double bonus for being a stylish ginger.

Not a style rider per se, but I had to post. 
"If I raised a certain amount of money for cystic fibrosis, I said I would run in a Peter Pan outfit for a week.”
Points for his designer, whose playful take on active wear makes Nike or Under Armour look like uncreative jocks. 

How’d you get your hair half light half dark?
"Oh that’s easy."
I like your style. 
"I like YOUR style!"
Points for wearing this kaleidoscope of colors that the evening sun popped in this glorious way; sweet smile.
Style rider on Hudson river and Christopher st. 

Are you heading to practice?
"No, just finished teaching music to a bunch of 2 year olds and their moms. I have 25 egg shakers in my basket here. But I’m in a band too. I share the same antics onstage that I do with the kids - just kind of letting myself go. It’s funny because the adults react to it in the same way the kids do."
Are you wearing black because it’s raining?
"No - I just always wear all black."
Bonus points: the contrast of bright bleached hair with black hood that initially caught my eye; great smile (captured in the above gif). To see some of the onstage antics, as well as her alter-ego, check out her band: jandthe9s
Style rider on Kent ave.

Do you normally wear a tie?
"No!! I was at school."
When did you start skateboarding?
"Just this year." (Note: he was a VERY good skater - super fast and weaving through traffic like a pro. Nearly killed myself just trying to keep up.)
Bonus points: listening to music throughout, he was basically dancing while he skated past the police precinct on Lorimer. Be sure to check out his Tumblr, it’s a good one: lnrboy
Style Rider on Lorimer St in Williamsburg

"My jeans? Oh they’re just ragandbonenewyork.”
Points for the sporty simplicity of her style - light white tee shirt, stonewashed tapered jeans and white slip-ons, no-frills jewelry; her bike, which was a Cannondale from the early 80s (she replaced the old gears with performance Shimanos) with leather Brooks seat. “I’ve taken this bike all over the world.” 
Style rider on Ave of the Americas

What are you doing?
"This is my spot. I love chilling by the river."
What do you like about your shirt (it had pineapples on it,)
"Generally, that there are pineapples on it."
Bonus points: this friendly young NYU student is also a poet - check out his tumblr, filixam