One of the questions I get asked most often (especially at this time of year) runs along the lines of, “How do you stay both warm & stylish in the winter?”
I hear you. I hear you big time. I’m always freezing, & when I’m cold I am cranky. So how to avoid looking like the Michelin Man in the winter? It’s easier than you might think! I’m here to help you look & feel your absolute best this winter.

First of all, you have to make sure you have the proper tools. You wouldn’t start to knit without needles, you wouldn’t fix your plumbing without a wrench, so you shouldn’t try to dress for super-cold weather without the right pieces of clothing in your arsenal.
Long-sleeved T-shirts. The ultimate layering tool. Get them in any colour & every colour which looks good on you. Get them a little long in the body & sleeves to peek out at the hem & cuffs for a hit of colour. Get them a little tight (you’ll not be wearing them by themselves anyway) to avoid adding additional bulk to your body.
Tights &/or leggings. Think of them as the long-sleeved T-shirt for your lower half. Choose colour accordingly.
Tall boots. Not just snow boots, but tall boots that wrap around your legs for a little extra warmy-warmy in your office or otherwise.
Long underwear. For those super-icy days. Silk are best, but I’ve had my L.L. Bean pair for seventeen years & they’re still going strong! (Of course, I don’t wear them very often…)
Legwarmers. Even just to fill in the gap between the top of your boot & the bottom of your skirt for the walk to the bus & back, you’ll be amazed at how warm they can be.
Lined skirts. It’s amazing what warmth a lining can bring to a simple skirt. Also, slickery linings prevent your skirt from sticking to your above-mentioned tights & leggings & crawling up around your bum under your coat.
Sweater dresses. Is it a sweater? Is it a dress? Does it matter if you’re warm?
Wool suits, trousers, & skirts. Wool, if you’re not allergic, is absolutely worth the higher price tag.
Vests. Can be styled in interesting ways, as long as they don’t scream GRANDMA or HIKING.
Scarves & wraps. A great way to add an extra dimension of colour & texture, plus bonus warmth. A scarf in the neckline of a dress shirt keeps your neck cozy, while a wrap over your dress, held with a great brooch, is a great way to add visual interest.
(Faux) fur accessories. More than just coats, you can find all kinds of muffs & wraps for old Hollywood glamour.

Having all the right tools doesn’t necessarily mean you know how to use them for ultimate warmth & style. There are tricks there too!
Wear tall boots with pants. There’s no rule saying tall boots go only with skirts. Throw them on under your pants with a pair of tights on & your calves will thank you.
Camisoles are your friend. Wear a close-fitting camisole (from your summer closet) under everything. If what you’re wearing has a low neckline, a camisole will provide a little bit of modesty if that’s how you roll, plus some bonus colour to tie things together.
High-necked garments need visual interest (most of the time). Pile on cool-looking chains, a large statement necklace, or a fantastic scarf. That being said, there’s an understated chic to a black turtleneck worn unadorned & with the hair up in a messy bun. Very Audrey Hepburn.
Break up monochromatic outfits. Use belts & shawls in interesting ways. Try belting a black sweater dress, then wearing a rectangular scarf across your body, tucked into the belt.
Make an effort to incorporate colour & shine. This time of year is dark & dreary enough, isn’t it? Worn layered, your colourful summer pieces can work in winter. Use a bright floral sleeveless dress as a skirt under a sweater. Or put on sparkly rhinestones. Anything that brings light to your outfit will be appreciated by all who see you.
Do you have any special tricks that you use to stay toasty-warm? Do you just suffer for your style? Do you say to hell with style in winter? Let me know in the comments or let’s talk on Twitter!

