The irony of looking sleek in the winter is piling on layers of clothing and not, as one would naturally assume, taking them off. “You don’t have the luxury of showing a lot of skin in the winter,” says Deborah Ferguson, a celebrity and fashion stylist based in New York. So if you’re going to be wearing a lot of layers this season, the trick is to pair them together smartly— think stylish, not bulky. And on that note, Ferguson shares her expert style tips to break down the art of layering this winter.

1. Get back to (winter fashion) basics
. Think of your basic investment pieces as ways to build up your look—when shopping, you should love each piece individually and as part of a larger overall outfit. “Go for a cashmere oversized boyfriend sweater,” says Ferguson. “It’s a good staple and on-trend this season.” Try as a cardigan or pullover, and pair over a denim button-up blouse (another key staple this season). Then if you’re heading out after the office, you can add a pair of killer earrings or a statement necklace for a night-ready ensemble.

HIGH-LOW DRESSING: 7 ways to make your outfit look expensive

An on-trend basic to try this winter is a classic shift dress. “It’s flattering to all sizes but still very directional,” says Ferguson. “It looks beautiful at any time of day. Pair with heels in the evening to add beautiful chicness to the look.” For successful holiday transitional dressing, keep your favourite statement necklaces on hand for post-work outfit changes. “In New York, we always have heels and jewellery in our bags!” says Ferguson.

2. Mix different fabrics and colours.
Consider playing with various textures and fabrications in one outfit. “A silk blouse is beautiful and will keep you warm in the winter,” she says (try an Equipment Signature Silk shirt in a fabulous red or aubergine colour). A lightweight silk-knit shirt in a classic tone is perfect for layering under a sequined blazer for a holiday party.

3. Add a cozy sweater.
Consider a cashmere-silk blend, which will keep you warm without risk of overheating (and makes for a great transitional item into next spring). “Invest in pieces that you will be comfortable in,” says Ferguson. “If you’re on the run, you want to be able to wear pieces without worrying about them.”

The 20 best WINTER 2014 coats

4. Add an oversized coat. This season’s key outerwear item—a fabulous shearling coat—happens to work perfectly over top of your outfit of layered basics. XXL coats in varying lengths and patterns were seen on the fall runways at Céline and Stella McCartney, with beautiful designs available from Acne Studios and Sandro at a more affordable price point.

5. Play around with different lengths. “I love it paired with a pencil skirt that falls to the mid calf,” says Ferguson. “And knee-high boots.” (Also great as stylish leather leg warmers.) And the oversized coat makes for interesting structural pairings—try with a skinny jean or trouser and heels for a chic statement.

6. Invest in winter fashion footwear. Tailor your footwear and leggings to the direction of your ensemble. A skirtsuit looks best when paired with feminine heels and fishnet tights (or bare skin, if you plan on spending most of the night indoors). For a more directly edgy look, go for a chunky heeled ankle boot and a thick wool sock.

How to really wear OVER-THE-KNEE BOOTS

7. And tights. “Thick, opaque Wolford tights last forever,” says Ferguson. Wear with pumps or ankle boots under a knee-length pencil skirt this season.

8. Accessorize with scarves.
Think of your scarf as a beautiful accent piece that tops off the rest of your winter fashion ensemble. “A faux-fur Fendi scarf is edgy and keeps you warms,” says Ferguson. Chunky knit cashmere scarves and neck wraps act as an interesting accessory, because once you remove your jacket, you have nice, warm piece that rests on your neck at a dinner party or restaurant. “Shop in a way that when you wear something, it becomes something else,” she says.

READ MORE:
Fall coats under $250 you can’t live without

5 ways to wear Fall 2014’s hottest fashion trends right now

10 super cozy fall sweaters
The hottest Fall 2014 shearling coats