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

There are few things in this world that bring out as much sheer anticipation and pure unadulterated joy as the all-mighty advent calendar. At this moment, somewhere in this world, two siblings are blissfully bickering over who gets to fling open today’s tiny door. If a piece of waxy chocolate can illicit that much excitement, imagine the happiness a glittery holiday manicure would bring. When I saw this mini nail polish advent calendar by the British brand Ciaté, I immediately thought what a perfect gift it would make for a friend (or me). Along with 17 of Ciaté’s best-selling shades, the set includes four caviar blends and three exclusive glitter shades for $58 (a $168 value). Buy it online at Nordstrom. Because what’s better than one present? Twenty-four presents, that’s what.

$58 at Nordstrom, 55 E. Grand Ave., 312-464-1515; or nordstrom.com

When does it make sense to fork over nearly four large on a pair of sunglasses you’re probably going to leave on the counter at Starbucks? Never, probably. And yet, there I was, flipping open the case to my new tortoise-framed Selima Optique Chad shades like that Indiana Jones character whose face melted after peering into the ark of the covenant. Why those particular sun-specs? Two words: Ryan Gosling. He wore the hell out of the frames in the movie Crazy, Stupid, Love, while telling a rumpled Steve Carell to “be better than the Gap” (slap!). I wanted to be better than the Gap. I wanted to look like Gosling (One out of two ain’t bad. Hint: Sorry Gap). OK, $385 hurt. But believe me, they really are works of art. Unless you find them on eBay, however, brace yourself for a wait. It took me a month on Selima’s list to get the call that they would deign to sell me the things. Was it worth it, Mr. Smith, you may ask? Call me Ryan.

$385 at selimaoptique.com

Sure, you’ve got the remainder of Hanukkah and Christmas to get through—but that doesn’t mean it’s too early to start planning that all-important New Year’s Eve ensemble. Attention, glitterati: You’ve waited all year for this, so rock that sequined frock with no inhibitions. For those of us looking to keep the pizzazz understated, might I suggest Kate Spade’s pretty, party-ready coin purse? It’s sized just right for stashing cab fare, lipgloss, and a handful of confetti, and it has a keyholder, too.

$50 at Kate Spade New York, 56 Oak St., 312-654-8853; or katespade.com

When the fashion flock abandoned classic square silk scarves years ago in favor of the long, voluminous rectangular variety, lovers of the former waited patiently for the style pendulum to swing back. If my recent reconnaissance work on the streets of New York City is any indication, that swing has begun. The perfect choice right now may be this 36-by-36-inch Hermès carré. No circa-1980s overembellished horseyness here—simply a graphic Op-Art-y chain print that delivers just the right punch of modern-meets-old lady. And the thick silk twill? Heavenly. Nab this scarf in red/orange, swirl it nonchalantly around your neck, and you’re good all winter.

$410 at Hermès, 25 E. Oak St., 312-787-8175; or usa.hermes.com

When I spied bright-colored laces threaded through the dress shoe displays at Nordstrom, my first thought was what a playful—and cheap—way to add a pop of pizzazz. Even better, a simple switch of lace color changed the entire look of the shoe. Suddenly, one pair became five. Can you really rock orange laces on brown brogues without being pegged as the office dandy? Absolutely. Made of organic cotton dyed with natural pigments.

$19.95 for a seven-pack, at Nordstrom, 55 E. Grand Ave., 312-464-1515 (shown with Cole Haan Air Colton Wingtip Oxfords, $198, at Nordstrom)

I recently stumbled upon Leif, an impeccably curated online shop brimming with baubles, wearables, and home accessories. Warning: It’s the kind of site that may lead to browsing away a good chunk of your morning if you’re not careful (oops). This quirky leather-and-mineral cuff made by Austin-based Sarah Murphy immediately caught my eye. Who said you can’t afford a jumbo rock? Though my jewelry collection tends toward granny-chic, for this piece, I’m willing to experiment with geologist-chic.

$72 at leifshop.com

While touring the shiny new Burberry flagship on Michigan Avenue, I’m told the Chicago outpost is the first in the country to carry the brand’s beauty line. Wait a minute. Burberry makes makeup? Indeed, and like the iconic trench coat, the offerings are simple, neutral, and classic—exactly what makeup should be for everyday purposes. “What’s your bestseller?” I ask. The hands-down, zero hesitation answer: Fresh Glow. A fluid, illuminating moisturizer, Fresh Glow has an ultra-fine shimmer to give skin a radiant—yet believable—brilliance. Mixed with foundation or applied straight to cheeks and brow bones, it’s like microdermabrasion in a bottle.

$48 at Burberry, 633 N. Michigan Ave., 312-786-2500; or nordstrom.com

With the holidays right around the corner, we’re all craving some flash and sparkle to brighten up our nights on the town. I love the contrast of the classic rhinestone and the electric punk threads woven through this Joomi Lim necklace. It will instantly elevate any outfit a notch in dressy-ness. Even if you get lazy and throw on a black dress, this piece will keep things interesting. Just add silver shoes and you’re ready to dance the night away.

$390 at Ikram, 15 E. Huron St., 312-587-1000; or joomilim.com