Beanie-covered heads bob in subway crowds and cashmere scarfs flutter in the wind as taxis whiz around the corner. As temperatures drop in New York City, the edgy rock their leather bomber jackets while the prim and proper don their wool peacoats and corduroy blazers.

In New York City, crosswalks are catwalks, and you can dare to wear whatever makes you strut your stuff. Whether you’re a guy flustered about fashion on his first trip to NYC, or a girl worried about her boyfriend’s gym-inspired clothes in the hippest parts of town, we’ve got the style laws and fashion faux pas for men traveling to the Big Apple this fall.

Recently we caught up with Megan Collins, the fashionista behind the men’s style website, Style Girlfriend. Megan is a go-to girl for finding the kinds of clothes women want to see guys wearing. Because she knows what’s hot or not for guys’ attire this autumn (and just about every other time of year), she gave us her top tips for making any upcoming NYC sojourns more stylish.

Fashion do’s

From floor-length faux fur coats and combat boots to Oxford button-ups and metal-studded motorcycle jackets, there sure are some weird and wonderful get-ups in this fad-crazed city. Megan explains, “When it comes to fashion here, anything goes!”

Megan Collins

This means it’s important that whatever you’re sporting in the city, you shouldn’t be shy. Vow to feel fierce and work the streets of crowded pedestrians. “Take advantage of the opportunity to try out a shirt or hat that’s a little outside your comfort zone,” says Megan. “You won’t get any funny stares here, though you just might get the oh-so-coveted nod of approval from a fashionable New Yorker on the street.”

Fashion don’ts

Still, Megan advises men not to get too crazy. “If you would cut the grass in it, leave it at home,” she cautions. Sorry guys, this means your tattered college sweatshirt and sweaty gym shoes are no-gos if you want to look stylish in this city. Megan says you don’t need to question your entire sense of style and buy a whole new wardrobe just for your NYC trip; you just need to pay attention to details.

Megan explains that your jacket, shoes, and bags can make or break a look. To avoid blowing your cover and sticking out like a tourist in NYC, she advises to “ditch the ratty sneakers and backpack for comfortable leather boots and a canvas bag.”

What to wear

While New York City certainly is the place for experimenting with style, the master herself admits that sometimes function trumps fashion. “You need items that can take you from a bike ride to a Broadway show to a restaurant to a bar,” she says. After all, NYC is an urban playground where you want to be prepared for anything and everything, all while looking the part.

Photo credit: Joselito Briones

To transition seamlessly from treasure-hunting at Brooklyn Flea to clinking glasses at rooftop bars in Manhattan, go for the layering effect. “Opt for layers that are more refined, like a light sweater over a button-up shirt, all under a streamlined blazer or leather jacket,” Megan suggests. Another must-have versatile option: desert boots. “This handsome footwear is dapper enough to take you from a walk in the park to dining at an amazing restaurant,” she says,

Where to shop

Modelesque city dwellers aren’t the only things that make NYC the fashion capital of the country. The trendy shops, vintage stores, and one-of-a-kind boutiques contribute significantly to the city’s unique sense of style, too.

Viewfinder Tip: Find menswear in shopping hot spots such as SoHo, the West Village, and Williamsburg.

Megan recommends SoHo as a must-stop place for guys to get a taste of retail therapy. “Carson Street Clothiers has a very modern and cool selection; you can also stop at Saturdays for surfwear and a coffee, and stock up on staples at the Bonobos Guideshop.” And for guys looking for some European flair, she adds, Topman is your spot. “The SoHo store is the only brick-and-mortar store for this U.K. brand in all of the United States,” she says.

The burning question

Let’s face it: After spending the day gallivanting around the city, all you really want to know is whether picking up an “I Love NY” shirt is a do or don’t. The verdict is in, and Megan says, “[It’s] a do! If the fit is right, an ‘I Love NY’ shirt is great souvenir to bring back home and dress up or down.” Phew!

The moral of this style story is that risk-tasking is a must on your fall adventures in New York City. Whether you’re prepping for a guys’ getaway or looking to appease your girlfriend, wear what makes you feel comfortable but confident, and use the streets of NYC as your fashion inspiration.

How would you describe your personal style when you travel?

**Photo credit on vertical picture: James Nord