Hey fellas, winter’s going to be here in, like, two minutes and the reality of our surroundings dictates that you’ll either have to dust off last year’s looks or head out to the shops for a seasonal upgrade. Granted, shopping for clothes doesn’t often rank high on the preferred activity list, but it’s wise to get a jump on rebooting the wardrobe before the wife/girlfriend/companion/mom insists on being your personal shopper. If you’re not sure what to look for, here are a few humble suggestions on what to wear this winter.

(credit: Bloomingdale's)

Black Turtleneck

The body loses a considerable amount of heat from the neck, and this fact alone should be enough to justify owning a turtleneck. Of course, sporting a black turtleneck has the added cache of subtle homage to the garment’s most trusted purveyor, Mr. Steve Jobs. It’s a timeless garment, which helps to justify a higher-end purchase, such as this one from Theory at Bloomingdale’s. Of course, a visit to Bloomie’s means you get to enter a super-cool old Masonic lodge, and that’s worth at least a fiver in my book.

(credit: Macy's)

Cord Jacket

I will admit I like the blazer trend. While it may seem like an obvious device for conveying forced sophistication, I say keep it going. Of course, for some people, the blazer is hardly a newfound layer. I had a friend in college who wore one every day, just because he felt a strange duty to present himself well in public. In a sea of sweats, sneakers and hoodies, he strode regally and buoyantly above it all like a proud extra from a Smiths video. He lives in L.A. now and is likely regarded as a fashionable gent since the everyday blazer has gone mainstream. Midwestern blazers of fashion trails should follow the compass to Macy’s (www.macys.com) and explore their fine collection of men’s corduroy jackets. Some good prices to be found there, too.


One of modern life’s great mysteries is the extreme and rapid disappearance of stylish headgear from the domes of the postwar American male population. Sure, we can chalk it up to late-60s hippiedom, but the extreme and rapid deletion of everyday head fashion in America is overdue for a reversal. Despite the fact that most people would agree that the fedora-clad PIs in mid-century film noir look is pretty cool, no one is actually willing to wear one in public in 2011. Some will never graduate beyond those ear warmer things or skull caps, and that is a cowardly shame. It takes a Daughtry to wear a knit beanie, and a truly bold dude to rock a fedora. Be the latter, please. The brave among us should head to Roosevelt Road to find a new headdress at Sids Clothing & Hats.

(credit: us.topshop.com)

Heavy Knitwear

Once in a great while fashion and practicality meet and bow respectfully to each other. This year, that crossroads is marked with a flag made of heavy knitwear. Maybe it’s the young dudes reconnecting with grandpa, or a sale on Hemingway Kindle downloads. Whatever, these things will rock the holiday fireplace. Just make sure you avoid the weirdly chunky ones. For your proper fitting, head to Topman on Michigan Avenue.

(credit: aldoshoes.com)

Leather Boots

There’s a natural tendency among the snow-averse to avoid wearing animal skins in wintry weather. IMO, that’s a little extreme. With proper care, a good pair of leather boots will long outlast the sidewalk slush and salt. Leather is a natural insulator, the warmth is inherent, and the style is beyond denial. You can wear these things to work without having to keep a pair of Wellies in reserve, and go out after with a red carpet underneath your soles. Get a pair of Palmrose leather boots at Aldo, 115 S. State Street, because the staff is friendly and when you walk out of the shop wearing these you’ll be rightfully fawned over by a coterie of UGG-booted Palmer House tourists.

(credit: shop.nordstrom.com)

Quilted Jacket

While a good wool coat will never go out of style, it doesn’t always win in the practicality department. It’s wise to have a reliable backup, and that’s where the quilted jacket comes in. The average (and all too common) North Face coat serves its utilitarian purpose, this year consider a quilted pattern without a brand name stitched on the shoulder. A solid weekend warmer, the quilted jacket (or vest) complements the casual side and provides a good amount of insulation without a lot of weight. You’ll find a good selection at Nordstrom.

(credit: Father Time Antiques)

Vintage Wristwatches

As the wristwatch is pretty much an anachronism at this point, it’s basically been relegated to fashion accessory status. The industry has understandably fought back by marketing wildly techy wristy thingies that can like read blood pressure and deflect bullets Wonder Woman-style or whatever, but they just look silly. Nothing beats finely-crafted sterling with an aged Swiss insignia. A solid, timeworn wristwatch says: I’ve got one foot firmly entrenched in the hallowed past, despite the ringtone blaring from my coat pocket. Anyway, an old wind-up watch is not just a cool accessory, it’s a sustainable, energy-efficient way to keep time. You’ll find a solid selection of eco-friendly vintage timepieces at Father Time Antiques.

Greg Wahl lives in Chicago and kind of misses shopping with mom.

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