Anyone who reads lots of fashion or style blogs should have heard of The Sartorialist. It’s an intelligent, photo-filled fashion blog filled with inspiring photographs of everyday people in interesting outfits on the streets in various cities.

A lot of the time you have to assume that the people Sartorialist founder Scott Schuman photographs are wearing vintage or secondhand finds because of the uniqueness of their clothing. Schuman does not often snap someone in identifiable clothing–i.e. anything with bold logos or recognizable graphics. The exception to the vintage assumption is, naturally, NY Fashion Week. The photos he takes in and around Bryant Park feature a lot of stylish women probably wearing a lot of expensive clothing. I doubt women wear anything from a secondhand shop to Fashion Week…unless it’s secondhand designer!

How can you emulate the cool, street-style of these women given their 15 seconds of fame via The Sartorialist?

I’ll show you.

This girl has managed to look both stylish, individual AND comfortable. Luckily, Victoria’s Secret makes a dress similar to the one she’s wearing:

Her gray shoes add a bit of flavor, where black shoes would have just melted into her tights. Try these from Payless. They’re cute and really inexpensive. To finish off, a black coat with a great cut and trendy quarter-length sleeves.

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Until attending school in Maryland, I never had a reason to buy boots. Sure, they were cute, but to a Southern Californian, they’re kind of like umbrellas or wool coats — you’d look fashionable wearing them, but everyone knew that they weren’t really necessary.

Then I encountered temperatures below 50 degrees and this thing called snow, and the need for boots became apparent to me. (Plus, I realized that I was missing out on a whole aspect of seasonal dressing!)

So, join me on my quest for the perfect collection of boots, won’t you?

These calf-high pewter leather boots look comfy and stylish — and they’re actually from Crocs’ new line, You by Crocs! Quite a deviation from their earlier work, no? (They’re also available in black and chocolate lambswool.)

A pair of cognac slouchy boots are a must for fall/winter dressing, and I bought these brown double buckle boots over the holidays — at a very affordable $39.50!

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Buying a coat this season just isn’t what it used to be. Thank God!

Circa 1995-2006, the routine was: enter store… feel force of pull to the racks laden with black wool… select shapeless style in the name of warmth and utility… hope for sale price… justify boring purchase with “It will go with everything!”… check out, go home, envy other people’s cool coats all season long.

Not this year. I’ve decided to forgo shapeless for a waist-cinching belt. I’ve decided to go for a 3/4 style so that the look is sophisticated, not like wearing the same wool peacoat I purchased in college or the long coats that make short people (like me!) look frumpy. I’m looking for color — maybe even pattern! And I’m willing to buy two — a conservative style as a classic investment piece, and then a moderate or cheap one “for fun.”

Here’s the catch — neither coat can be black, unless that black is in a pattern. That’s the whole point of this style update — break out! I’d like the investment piece to be neutral — after all, I do have to look professional and a bubble-gum pink wool coat likely won’t have me taken very seriously. But the “fun” piece can be as bold as I dare.

So right now starts the No-Frump Winter Coat Challenge. I’ve started adding a few contenders to my StyleFeed… let me know what you think.

Should I go for a to-die-for color?

Fun pattern and a belt?

Frilly, feminine details?

Hurry, people! It’s getting chilly!