You physically can’t trot around in skyscraper heels 24/7, so flat shoes are a necessity—especially the ladylike kind that you can wear on the street, with a dress, on a lovely spring day. But if your feet are on the large side, choosing flats that flatter can be a challenge. A pointy toe is out (it adds length), as is patent leather (shine = volume). To the rescue: The calfskin cap-toe ballerina pictured here. Its light flesh tone matches the pasty legs of a typical Chicagoan (of Irish heritage, anyway) emerging from her winter cocoon, and the rounded black cap toe visually shortens the foot. While Chanel makes the classic version, I prefer the Prada, which has a somewhat sturdier feel—and somewhat kinder price. It’s the best friend a bigfoot ever had.

$550 at Neiman Marcus, 737 N. Michigan Ave., 312-642-5900

With New York Fashion Week here, I had to build my arsenal of chic ensembles that would allow me to tromp around from show to show without getting frostbite.  I absolutely hate being cold, and although the weather forecasts don’t look too bad, walking outside most of the day in 40 degree weather can be bone chilling.  Leather pants and leggings are an essential staple in combating the cold, and here is a refreshingly slouchy silhouette in a gorgeous blue-grey hue that will keep me looking cool while helping me stay warm.

$1,345 at helmutlang.com or Saks.com
 

Years ago, my flat iron and I were an inseparable duo. I would mash my naturally wavy (nice way of saying frizzy) strands through the metal plates of my Chi every day. Religiously. My hair was straight and sleek, but dear lord was it damaged. I’ve found the key to eliminating the flat iron from my life is with an at-home blow out using a boar bristle round brush. Specifically, the 2 1/2-inch Marilyn Tuxedo Pro Brush, a hairdresser favorite. The bristles have the perfect amount of grip to add body and smooth out strands, plus the ceramic core heats up to lock in curl.

$23 at ulta.com
 

Designer shirts are nice and, yes, a couple of custom-made shirts are a must in a gentleman’s closet. But there’s always a place for a soft, beefy, well-constructed oxford, either to wear with a blazer or layer with a sweater. That’s particularly so with the weather returning to more Chicago-like snow and chill. Enter the Oxford Flannel shirt in light gray by Individualized Shirts. Not only is it made of two-ply worsted cotton, it is made in the U.S., and sold at Inland Clothing, which is committed to goods produced “by workers who enjoy U.S. wages, labor protections, and working conditions.” Yes, the shirt costs a little more, but the quality and ethos makes it well worth it.
 

$134 at inlandclothing.com

If Kelly Kapowski of the early ’90s sitcom Saved by the Bell walked into Wicker Park’s Una Mae’s, I’m betting she’d beeline to this perky lace top. For better or worse, cropped is back, and it’s just as stylish today as it was during Kelly’s years at Bayside High. That said, an exposed back zipper and cuffed sleeves add a dash of sex appeal and make this top more Girls.

$54 at Una Mae's, 1528 N. Milwaukee Ave., 773-276-7002
 

I have become a big fan of Etsy (etsy.com) as a place to find independent artisans around the country and beyond who are doing interesting work. While you do have to wade through quite a few, shall we say, non-classic choices, a recent spin through the handmade jewelry section turned up the strong, simple work of Laurie Luttrell. She lives north of the border (in Muskoka, the lucky duck) and can make this striking bezel-set ring in any size and finish you like—how great is that? Even greater is the price, especially given that this is fine jewelry and that it will never go out of style. A Valentine's Day gift to yourself, perhaps?

$50 at etsy.com/shop/luttrellstudio

Bag shopping can be fraught with complexity. There are so many factors to consider: color, size, shape, strap length, price. And the fact that, ideally, it should work with most of your wardrobe. I also shy away from totes that are ubiquitous, logo-ridden or weigh more than a healthy newborn baby. Given my long list of criteria, it’s infrequent that I come across a bag that I’d want to include in my small collection of Chosen Ones. But I love everything about this beauty from Acne—the contrasting neutral shades, the sturdy leather, and the stiff fringe that is both masculine and feminine. Plus, the versatile cross body strap will do well over winter coats or spring dresses.

$410 at stevenalan.com

When it comes to my wardrobe, I’m a high-low girl. Splurge on some items; scavenge for the others. My makeup bag is the same—Yves Saint Laurent lipstick; Cover Girl mascara. But when I heard people singing the praises of a $3 makeup brush, even I was skeptical. Cheap brushes have uncomfortably stiff bristles that shed incessantly. I stand behind that statement, but found the exception to this rule: the Studio Powder Brush by e.l.f. It’s designed to be used with both wet and dry products, and it’s particularly phenomenal with foundation. I use it to blend mine, and its super soft bristles create an airbrushed finish. All for three measly bucks.

$3 at eyeslipsface.com

When is a gray suit not a gray suit? When it’s the beautiful gunmetal blue/gray “James Sharp” knockout I saw recently at Hugo Boss. The star of this Italian shorn wool ensemble is a traditional two-button jacket that has a five-button vest, with black vents on either side and contrasting under-collar and jacket lining. “Since last year, two things have been blowing off the shelves,” sales consultant, Quintin Torres told me. “Double-breasted and three-piece suits.” What makes this piece different, besides Boss’s impeccable fit and cut, is its blue/gray hue. It stopped me, and, despite the fact that I have three gray suits, with this unusual number, I could certainly see making it four.

$945 at Hugo Boss, Shops at Northbridge, 520 N. Michigan Ave., 312-321-0700
 

Last week’s extreme winterishness had me craving all sorts of things. While most are edible (and laden with butter), I’ve also been craving some color in my life—you know, hue therapy. Hello, spunky little wristwatches from Minneapolis-based Taki Watches! Sleek leather bands offset by a cheerily colored face—they’re like a shot of vitamin D on a dreary January day.

$80 at Hazel, 1902 W. Montrose Ave., 773-769-2227