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Image courtesy AMC

What would Don Draper do? Careful down that road. You might end up wasted, fired or worse.

But what would Don Draper wear? Better question.

The enigmatic and pathological main character of AMC’s Mad Men TV show dresses sharp, with a “classic gentleman” look built on straightforward ties, tan car coats, oxfords or derby shoes–and when stepping out: black tuxedo.

To really get in touch with Draper’s style, remember consistency is key. Pretty much the only change in his wardrobe as Mad Men arced from the 1960s to the 1970s was that he started wearing more stripes.

Clothes and accessories to keep you draped up and dripped out, so to speak:

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The Sneaker Project is a curated selection of sneakers handpicked by our buyers, and forgive our immodesty here, but it rules. Twice a year we give it an extra dimension with atmospheric videos shot in various cities. We pick a sneaker enthusiast and make them our tour guide. So far we’ve profiled Seattle, New York and now Los Angeles.

Our L.A. video was made by and stars Dan Regan and his actor friend Spencer Lofranco. Regan is a downtown L.A. dweller and Venice neighborhood local, an artist/photographer/director we admire–someone whose professional title could probably be something nebulous like “creative strategist and digital fathomer,” but that’s obnoxious and he’s not.

In fact, he’s pretty much the man for steering us away from #basicstuff in Venice and recommending a few crucial spots to chill and eat. Check out our Q&A and some behind-the-scenes snapshots below.

Shop: The Sneaker Project

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The star of all-star jam “FourFiveSeconds” is definitely Rihanna, singing hard and being a badass and crying, performing with Sir Paul McCartney and the current King of Pop, Kanye West. Not the first time McCartney has collaborated with the K.o.P., BTW.

But from a style POV? The star is Rihanna’s jean jacket and leather-belt-tied-like-a-tie combo. Kanye West did the styling, selecting vintage Sean Jean denim. Which means for all you retro trend watchers out there, it’s time dig up your late-’90s/turn-of-the-millennium hip-hop gear like Fubu and Karl Kani.

That’s the fashion tip.

Shop: Men’s Denim Jackets

–Andrew Matson

How should you shop our ongoing men’s sale, where drastic, half-off discounts abound? It’s about looking past the racks on racks on racks–and seeing what’s really present. At our flagship store, a salesperson advised a deep dive for AG denim: “It’s there if you look. It only goes on sale a few times per year, if that.”

Rare gems with commentary from a recent walk-through:

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 The best way to really get your money’s worth; make your wardrobe multitask. Here, Men’s Stylist Brenna Carlson schools us on five distinct and sharp looks for a casual jacket.

Field jackets are made to be tough. Utilizing a design honed over decades, designers put waxed canvas, corduroy and wool to task, shielding the wearer from elements on any adventure. I styled a Barbour jacketan older, tougher version of your go-to leather jacket and a rugged complement to any wardrobe—for the office or a casual date, or really any occasion that needs a little edge.

Five different ways to wear a coat

Office Ready: Field jackets are always on standby for the weekend, but try switching out your weekday suit jacket for this unconventional topcoat alternative.

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In the late ’70s, American men’s workwear was rugged and woolly, cut like military clothing but trimmer–it looked good and never fell apart. Today we call this fashion. In that vein, we salute brands that have stayed busy not fixing what wasn’t broken, like Filson and Pendleton. Images below are from the Nordstrom vaults. Links are there to help you find the modern counterparts.

Filson Mackinaw Cruiser Wool Jacket | Pendleton Trail Trim Fit Wool Woven Shirt

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Plaid: it’s as old as the hills. But today’s best applications of ages-old tartan patterns take that traditional country club madras and your grandfather’s Sansabelts and throw a handful of future at them. Urban bravehearts hoping to steer clear of geezerville should aim for flat fronts and slim, even slightly cropped legs. And it goes without saying (but we will just in case): pair solid tops with checks, please.

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Paul Smith London ‘Kensington’BOSS HUGO BOSS ‘Sharp’ | Junya Watanabe ‘Patchwork’

SHOP: More Fall/Winter Trends | All Designer Pants

Our guest editor Thig Nat (right)—a polished professional by day, hip-hop musician and talented photographer by night—possesses an innate sense of style that shines through on the microphone as much as it does in his personal appearance.

Keep reading for a look inside Thig’s creative process as his band, The Physics, heads back into the studio—and to see his favorite fall items that work as hard as they play.

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The thing about the monk strap is that it’s a very statement-y classic. On the continuum of classics from subtle to strong, it hits the right end of the spectrum, and rings a couple of bells and whistles while it’s there. Smart, sophisticated bells and whistles, though. Think, free jazz bells and whistles. Think, well, Thelonious Monk.

We typically stay away from blanket statements, but in today’s jogger pants-with-a-sport-coat economy, you really can’t go wrong with this style: put it with a sharp, slightly short trouser or throw it under some cuffed premium denim. For your consideration: three of our favorite specimens.

To Boot New York ‘Burns’ | Prada ‘Spazzolato’ | Northern Cobbler Double

SHOP: Monk-Strap and Double Monk-Strap Loafers
SHOP: Our Favorite Fall Shoes

Are you acquainted with our Complete Looks page? It’s where we post head-to-toe kits assembled by the pro stylists at our photo studio, and give you links to easily shop each item shown.

As you can see above, there’s a lot to choose from. To help you narrow the field, we asked Chad Christensen—lead men’s stylist at our Seattle photo studio and the man who builds said looks—to answer a perennial office conundrum: how to look better than the guy in the next cube.

Keep reading to see Chad’s three key items for fall—which will serve you well from work to weekend.

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