Sometimes it’s the details that make the difference between meh and must-have. Case in point: Burberry’s wool-blend twill jacket. It’s a bomber shape (hard to get more classic than that), but designer Christopher Bailey has played with proportion just enough to make it feel completely fresh. Add subtle zigzag stitching on the placket and black edging on a field of navy and you’ve got a winner in my book. Of course, there’s no way this thing can cut a Chicago winter (it’s technically outerwear), but who cares? I’d sport it as an indoor jacket over a crisp white shirt and black skinny pants—and smugly tell anyone who wants to crank down the thermostat to go right ahead.

$795 at Burberry, 633 N. Michigan Ave., 312-787-2500; or burberry.com

After years of battling between the need to stay warm or look chic, I finally made an investment in a good shearling coat.  No longer am I shivering in cocktail attire on frigid Chicago nights or scared of my mummy-like reflection walking down Michigan Avenue when the temps are below zero. Last week I saw this beauty of a shearling jacket and was blown away at the quality and fabulous cut being offered at AllSaints Spitalfields, which the fashion set often refers to as “high street” (and which my co-blogger Bryan Smith also has a thing for).  It is still quite an investment, but the combination of warmth, coziness and stylishness are all worth it in my book.

$1,450 at AllSaints Spitalfields, 700 N. Michigan Ave., 312-283-0400; or allsaints.com

As much as I enjoy browsing at Topman on Michigan Avenue, there is rarely anything there for me. Loathe as I am to admit it, I no longer have the heroin-chic, skin-and-bones physique to rock their super-skinny bright-blue pants. Not to mention, I’m a little too, ahem, old for that look. But one thing I consistently find there that keeps me coming back: shoes. Brogues, loafers, plimsolls, sneakers—they have them all, and often for a song. I have built quite a collection of $50 to $80 Topman shoes because I’ve been willing to wait and willing to pop in on a regular basis for a price status check. Every pair has looked great and worn remarkably well. Currently, I have my eye on the Peter 2 Boots. They aren’t on sale yet. But when they are, I’ll be ready to pounce.

$170 at Topman, 830 N. Michigan Ave.  312-280-6834; or topman.com

You know that scene in Hitchcock’s Rear Window when Grace Kelly coolly clicks open her boxy Mark Cross handbag and a silk negligee foams out of it? I’ve been obsessed with that bag ever since I saw the movie in my early 20s. So earlier this year, when an updated version of this exact same Mark Cross bag appeared at Barneys, I began strategizing-slash-rationalizing the purchase of one of my own. Like the one Grace toted, this minimalist black calf-leather beauty holds far more than its relatively modest size (6.5 by 8.25 by 4.25 inches) might indicate—but unlike hers, it comes with a removable shoulder strap. (Which I intend to ditch immediately. Why mess with perfection?)

$1,995 at Barneys New York, 15 East Oak St., 312-587-1700; or barneys.com

Anyone who knows me can tell you that I am a serious Isabel Marant fan.  My obsession started one summer in the late ’90s when I came upon the label at Barneys in New York while I was interning there as college student. I bought a perfectly slouchy black wool skirt with a beautiful big leather button that’s still in my closet now. When I saw this sweater the other day, it brought me back to that moment years ago. Marant has a knack for taking a classic French look (in this case, the chunky cream cable-knit) and giving it a sexy and modern twist (see the asymmetric hem). It will look great with slim-legged pants or a body-hugging skirt and tights. And, of course, it is warm and snug to boot!

$700 at netaporter.com

There are pea coats and there are pea coats. There’s the classic, Navy surplus, Old Spice commercial version, of course. Then there are the oceans full of modern interpretations, with as many styles as a bowl of freshly shucked pods. Until this season, I’ve gone old-school, as if I just stepped off a long sea voyage. Then I came across the Kaledin pea coat at AllSaints Spitalfields on Michigan Avenue and my wallet flapped open like a tuna in a skiff. Crafted from fine Italian wool and lined in Italian twill, it also has a concealed fly-button fastening, peak lapels and real horn buttons. It is slim-fitting, but not so skinny that I have to do P90X to sail away in style.

$435 at AllSaints Spitalfields, 700 N. Michigan Ave., 312-283-0400; or allsaints.com

Ever since it opened this past summer in River North, the blow-dry bar Blowtique has been doling out ’dos with three-day staying power to many a happy customer. Now the salon offers a Blow-Out Survival Kit—a perfect gift for mom, sister-in-law, boss, or bridesmaid. After all, the gift of a good hair day is appreciated by all. The kit includes a terry-lined shower cap, a purse-size dry texturizing spray by Oribe, and a handful of alligator clips.

$35 at Blowtique, 1 E. Huron St., 312-280-2400; or blowtique.com

One of my friends always helps me justify purchases by estimating said item’s CPW (Cost Per Wear) ratio, which is found by taking the total cost of the item and dividing it by the estimated number of days you’ll wear it. I never actually do the math, but I frequently use the idea to convince myself that jeans are actually quite inexpensive. The same holds true for this ultrasoft, wool/cashmere beauty I spied at Penelope’s in Wicker Park. Ninety-eight bucks is well-spent when it goes toward a piece versatile enough to add color to the oh-so-blah black parka, look luxe with a button-down at the office, and morph into a cozy blanket while curling up with a mug of hot cocoa. So, as far as I’m concerned, this baby is basically free.

$98 at Penelope’s, 1913 W. Division St., 773.395.2351; or shoppenelopes.com

In theory, sweater dresses are great winter staples: So easy! So cozy! But they’re also prone to bagging out sloppily over the course of the day—or, conversely, clinging unattractively below the waist after an especially robust meal. This one was carefully designed to avoid such infractions. The fit-and-flare style banishes dreaded lower-anatomy cling; the silk/angora blend is neither too wispy nor too heavy; and the classic stripes mean it will remain in style for a long, long time.

$495 at Tory Burch, 45 E. Oak St., 312-280-0010; or toryburch.com

It’s getting harder and harder to find runway-worthy shoes at reasonable prices. Four figures seems to be the norm these days, but I refuse to give in to the ridiculousness. Fortunately, Gianvito Rossi is making shoes I want at a (relatively) reasonable price. These suede beauties with their slender heels and flattering cut make my legs look thin and elegant, and their minimalist shape is super-sexy. The best part? I’ll be able to wear them year-round: in the winter with black tights; in the summer, with bare legs and a white sleeveless dress. Now that is a good investment.

$635 at Barneys, 15 E. Oak St., 312-587-1700; or barneys.com