How to Wow This Winter in Woolen Skirts and Dresses

By Kaia Saunders / February 6, 2017
Pretty blonde in grey woolen skirt and grey turtleneck sweater

The winter season typically means layers of warm, cozy fabrics, covering us from head to toe. This year, though, it’s all about baring some leg in the trendiest, most stylish woolen skirts and dresses.

From printed plaid designs and A-line miniskirts to fitted pencil styles and pleated midi skirts, the tone of the season is feminine and fabulous. We’ve collected some of the most fashionable woolen skirts and dresses in every shape and style to inspire you to explore this chic winter trend.

Wearing Woolen Skirt for Warmth and Style

1) Gorgeously Gray

Pretty blonde in grey woolen skirt and grey turtleneck sweater

An ensemble of matching grey separates is a lesson in elegance (photo: looktastic.com)

This look is pure class. A lush woolen turtleneck sweater is paired elegantly with a sleek woolen pencil skirt in matching gray.

Wearing two items in the same color makes the whole body appear to be slimmer, not to mention a cinched-in waist for more defined feminine curves. This ensemble is the ideal choice for work days that lead into fancy cocktail parties at night. To amplify the chic effect, opt for pretty suede stiletto heels in the same shade of gray.

2) Pretty Preppy

Stylish blonde in woolen skirt and dark brown suede brogue boots

A pleated woolen skirt as your preppy style (photo: devonrachel.com)

When the sun is out and days are bright, why not celebrate the cheerful weather in a preppy little woolen skirt? The cheeky pleated detail adds to the charming style of this winter fashion essential. Complement the contemporary look with a two-tone woolen sweater and cute brown suede lace-up booties. Round-rimmed tortoiseshell sunglasses and a beige fold over clutch purse complete the look.

3) Layered in Lambswool

Cute brunette in grey woolen skirt and light grey woolen sweater

A lambswool sweater is paired prettily with a pleated woolen mini skirt (photo: stylecaster.com)

Think you can’t indulge in the woolen skirt trend during the chilly winter months? Think again. This ensemble shows us how it’s done, with a pleated woolen mini skirt paired perfectly with black opaque tights and platform strappy sandals. Adding to the cozy, comfortable style is a crew neck sweater in light gray lamb’s wool. This ensemble is cute and ladylike, polished off sweetly with a large black leather handbag.

4) School Run

Brunette woman in black woolen pencil skirt and coral cardigan

A sleek pencil skirt adds sophistication to this office ensemble (photo: schonefrau.com)

Channel your inner schoolteacher with this sweet ladylike ensemble. A sleek black woolen pencil skirt streamlines the figure beautifully. On the top half, we find a beige ruffle top worn underneath a coral-colored cardigan. Comfortable camel sandals polish off the elegant effect.

5) Street Smart

Edgy woman in charcoal woolen mini skirt with black leather jacket

A fit-and-flare woolen skirt gets an edgy twist with a touch of leather (photo: whowhatwear.co.uk)

Here is a look that oozes edge and sex appeal. The combination of a fit-and-flare mini skirt together with a grungy leather jacket is cool and contemporary. A basic white T-shirt keeps things classic while black pointy stiletto heels add some sophistication to this modern city look.

6) Cute prints

Woman in woollen skirt with prints
Woman in woollen skirt with prints (photo: bagatyou.com)

If quirky and eclectic is more your style, a printed woolen skirt was designed just for you.

7) Simpler is Better

Stylish brunette in mustard woolen skirt and grey woolen sweater

Opt for a bright woolen skirt when need style and comfort (photo: whowhatwear.co.uk)

Everyday living calls for versatile clothing that is stylish yet comfortable. A wrap skirt in mustard-colored wool fits the bill perfectly. The perfect addition is a simple fitted gray woolen sweater. Tying it all together elegantly are a pair of structured black sunglasses and a chic sling handbag.

8) Minimalistic Mode

Elegant blonde in midi grey wrap woolen skirt and white fitted T-shirt

A woolen pencil wrap skirt needs only a simple white T-shirt for ultimate style (photo: cichic.com)

Keep it slim, trim and tailored in a beautiful midi pencil wrap skirt in dark gray wool.

This look is polished and ladylike, ideal for a day spent at the office when your style needs to be stylish yet functional. Pair it simply with a fitted white T-shirt and black jacket. Strappy black stiletto sandals complete the look with the accessories kept chic and minimalistic.

9) Stylish in Salmon

Stylish brunette in grey tweed woolen skirt and coral blazer

Mix and match your favorite items for a blend of sporty and sophisticated (photo: withlovefromkat.com)

Create your own authentic winter style by pairing your favorite cold-weather items into one unique ensemble. Here we see blogger Kat Tanita take a sporty gray tweed woolen skirt and match it with a soft silk navy blue blouse. To add a sophisticated edge, she opts for a salmon-colored coat plus a beige Prada handbag and stacks of gold jewelry.

10) Midriff Magic

Blonde woman in grey woolen pencil skirt and matching woolen crop top

Is it a dress? Or is it a skirt? It’s all in how you style this top-and-skirt combo (photo: wachabuy.com)

This top-and-skirt combo could easily pass for a dress. It all comes down to the way in which you style it. In this ensemble, we see a light gray woolen pencil skirt worn high on the midriff. With only a sliver of skin on show, a matching woolen crop top coordinates the look beautifully. White statement heels add a sophisticated touch, as do a black Chanel handbag and brown woolen coat draped casually off the shoulder.

11) Plaid Princess

Pretty blonde in plaid woolen skirt and grey woolen sweater

A plaid woolen A-line skirt brings all the drama to this leggy look (photo: laceandlocks.com)

Elegant yet preppy is the effect when a light gray woolen sweater meets a brightly patterned skirt. This fitted A-line mini skirt is made of blue and purple patterned wool. In contrast, the top consists of finely woven light gray wool. The chosen accessories are kept neutral, like camel-colored strappy peep-toe heels and a brown sling handbag plus a metallic silver necklace.

12) Basically Beautiful

Chic blonde in black turtleneck top and grey wrap woolen skirt

Stylish grey plaid plays perfectly over a basis of solid black (photo: eslamoda.com)

To create a chic, modern aesthetic, you can never go wrong with classic black matched with light gray. This look, for example, consists of these two neutral shades blended to perfection. A black turtleneck sweater and thigh-high black leather boots serve as a stylish basic canvas. Contrasting beautifully against this color is a woolen wrap skirt covered in a large plaid pattern. A structured gray tote bag completes the elegant city motif.

13) Burgundy Bliss

Chic redhead in burgundy midi woolen skirt and black blouse

Beautiful burgundy adds a nostalgic feel to this A-line woolen skirt (photo: tumblr.com)

Give a refined, old-fashioned touch to the woolen skirt trend. This look is elegant, classy and ladylike, thanks to an A-line pleated midi skirt in beautiful burgundy-colored wool. A thin dark brown leather belt sits prettily around the waist while a short-sleeved black blouse is simple and classic on the top. Black socks with black lace-up boots add to the nostalgic feel.

14) Pretty in Pleats

Chic woman in midi pleated woolen skirt and blush woolen sweater

Keep it elegant in light grey woolen pleats (photo: closetfulofclothes.com)

Unsure of how to style a midi pleated skirt? The trick is to keep the rest of your outfit as simple as possible. The longer length of this woolen skirt combined with the pleated detailing are all the pizzazz you need to create a striking look. Pair it with a simple top in a soft draped fabric before polishing off the look with brown suede sandals. A brown leather purse is a nice simple way to incorporate more color into the ensemble.

15) Polka Dot Pizzazz

Stylish blonde in woolen mini skirt and polka dot blouse

Go a little dotty! (photo: fashiongum.com)

Here we have an ensemble that is designed to show off the quirky side of your personality. This look combines two of this season’s hottest trends: polka dots and pleated skirts. A black-and-white button-up blouse is tucked into the waistband of a pleated navy blue woolen mini skirt. To add extra spunk to the unique pairing, throw on some 60s-inspired T-bar platform stiletto sandals.

16) Pastel Perfection

Cute brunette in grey turtleneck woolen sweater and grey woolen skirt

Combine your favorite shades of grey into one casually chic ensemble (photo: somethingnavy.com)

Pastel shades will always add a certain vintage glamour to your outfit, as can be seen in this chic winter ensemble. An oversized turtleneck sweater is paired with a woolen mini skirt in a darker shade. The boots are in an even darker color of gray suede while a Chanel handbag in metallic silver is worn casually over the shoulder. This look is chic yet still casual and perfect for informal winter days.

17) Penciled In

Elegant woman in grey pencil woolen skirt and black vest
Subtle lace-up detailing adds some edge to this woolen pencil skirt (photo: hapatime.com)

When the weather brightens up a bit and you’re willing to show some skin, dust off those ankle-strap stiletto sandals for an elegant yet understated winter-inspired look. This sleek pencil skirt is made of ribbed gray wool with a lace-up slit along the side. In contrast, we find a simple black vest which picks up the color of a structured black leather handbag and slimming black stiletto heels.

18) Gossip Girl Gorgeous

Preppy woman in brown woolen sweater and pleated woolen mini skirt

Draw inspiration from the preppy teens of Gossip Girl and you’ve got a style winner (photo: moonlight-over-paris.tumblr.com)

Here we find a prep-school take on the fashionable pleated skirt trend. Imagine the characters of Gossip Girl taking on the streets of New York in 2017. All that’s needed is a trendy little woolen pleated skirt co-coordinated with a cable knit woolen sweater in rustic copper. An unexpected touch comes in the form of a collared white button-down shirt peeking out underneath. Complete the look with black opaque tights and stylish round-rimmed black sunglasses.

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How To Look Elegant With Woolen Dress In Winter

19) Luxuriously Layered

Trendy brunette in dark grey woolen dress and long grey coat

A simple grey woolen shift dress serves as a stylish blank canvas (photo: gofeminin.de)

Layering luxurious fabrics is one of the best parts of winter dressing. This outfit uses a simple gray woolen shift dress as a backdrop to show off other style items to perfection. A black pashmina scarf is draped elegantly around the neck while sheer black stockings and knee-high black boots add sophistication down below. Tying it all together is a men-style dark gray coat and gray sling handbag.

20) Brogue Beauty

Trendy woman in grey woolen sweater dress and brown brogue shoes

For winter style on the run, throw on a woolen sweater dress and classic brogues (photo: tumblr.com)

This look takes on the oversized sweater trend and turns it into a bona fide winter winner. When comfort is at the top of your list, there’s nothing as cozy and effortless as a woolen sweater dress. This gray cable knit number is paired casually with olive green knee-high socks and light brown brogues. Accessories are kept simple with black aviator sunglasses and a black leather sling handbag.

21) White Alright

Stylish woman in white off-the-shoulder woolen dress and brown suede boots

Feminine flair shines through in an outfit of pure winter white (photo: styleoholic.com)

Celebrate your femininity even when the weather outside is grim and gloomy. This off-the-shoulder woolen dress is perfect in pure white. Polishing off the chic effect is a pair of brown suede knee-high boots as well as a dark brown sling handbag. Keep the accessories to a minimum, as seen here with only oversized sunglasses perched high on the head.

22) Black Excellence

Stylish brunette in black turtleneck woolen sweater dress and black boots

All black is all right for glamorous winter style (photo: stylesweekly.com)

Nothing says understated glamour quite like an outfit of all black from head to toe. This turtleneck ribbed woolen dress skims the body ever so elegantly, with a black leather belt slung low on the hips. Black sheer tights are worn with knee-high black leather boots while a dainty chain handbag breaks the monochrome color.

23) Bold and Beautiful

Chic blonde in red and black patterned woolen dress and statement heels

Be bold and daring in a patterned woolen dress for maximum style points (photo: tuulavintage.com)

When the occasion calls for a fashion statement, look no further than a midi-length fitted woolen dress. While the body-hugging style keeps you warm and cozy, it’s the bold red-and-black pattern that steals all the attention.

Be sure to choose equally glamorous footwear, like this pair of ankle-strap stiletto heels. This look requires no further accessories, except a basic clutch purse and a simple gold ring.

24) Style Silhouette

Chic brunette in off-the-shoulder grey woolen dress and black clutch purse

The fitted silhouette of this woolen dress creates a style stunner (photo: styleoholic.com)

This look may be the ultimate in glamorous winter style. The woolen fabric is thick and decadent, providing ample warmth on a cold winter’s night. The fit keeps it classy, with the body-hugging silhouette contrasted with a looser, more draped effect on the top. A simple black handbag plus red nails complete the simple, sophisticated ensemble.

25) Pretty Panache

Glamorous woman in white turtleneck midi woolen dress and brown hat

Play the part of Pretty Woman in this elegant ensemble of white and brown (photo: amolusso.com)

Channel your inner Pretty Woman in this stylish ensemble of pure white and brown. A midi-length turtleneck dress like this one is an investment piece which can be worn in countless different ways.

Here, it is paired simply with a stylish wide-rimmed brown hat, nude pointy-toed stiletto heels and a brown-and-white sling handbag – perfect for a day at the races or simply imagining you were there.

26) Urban Cool

Stylish blonde in grey turtleneck woolen dress and black thigh-high boots

High fashion meets urban street style (photo: blogg.damernasvarld.se)

Here is a look that expertly combines high fashion with edgy street style. A gray woolen turtleneck sweater dress is warm and plush under an eye-catching black-and-white plaid coat. The look receives a grungy, edgy effect with the addition of slouchy knee-high black boots plus a shiny black leather handbag.

27) Front Row Finesse

Stylish brunette in navy blue woolen dress and black leather boots

Be a vision in navy blue in this midi woolen dress straight off the runway (photo: becauseimaddicted.net)

You’ll be a vision in navy blue wearing this midi-length turtleneck woolen dress. An outfit all in itself, little else is needed to complete this look. Adding ever so subtly to the glamour are a basic clutch purse as well as pointy black leather boots. You’ll be equally at home sitting front row at fashion week as you will be on a hot Saturday night date.

28) Body-skimming Basics

Chic blonde in grey woolen dress and knee-high suede boots

This comfortable body-skimming woolen dress is ideal for all-day wear (photo: bostonproper.com)

Is there anything more classic and sophisticated than a woolen dress in a soft neutral color? This beautiful gray dress hits all the style marks with its turned-up collar and gentle V-neckline. Best of all, the soft fabric is lightly body-skimming making it warm yet comfortable enough to wear throughout the day. The simple look is polished off with knee-high suede boots in dark gray.

29) Military Must-have

Pretty brunette in grey sweater dress and navy blue military coat

A blend of cute and classic as grey wool combines with classic military style (photo: hapatime.com)

Pretty meets sophisticated in this sweet winter ensemble. Mastering the woolen dress aesthetic, blogger Jessica Ricks knows how to combine trends to create a standout look. Her gray woolen dress is perfectly tailored to accentuate her curves leading down into black opaque tights and finally black leather ankle booties. A contemporary touch comes in the form of a navy blue military coat casually hanging off her shoulder plus a black leather Prada handbag.

30) Invest in Style

Chic blonde in navy blue sweater dress, brown belt, and brown heels

This versatile woolen dress is an investment piece to last you a lifetime (photo: memorandum.com)

Versatility is the name of the game with this beautiful navy blue woolen dress. In soft brushed wool, the fabric lightly skims the body which accentuates the feminine curves ever so subtly. It’s the neckline that truly sets it apart, though. Depending on the event, this dress can be styled as an off-the-shoulder number, a one-shoulder piece or a cowl neck creation (as seen above). Accessories should also be kept to a minimum. Here we see a brown belt around the midriff, basic brown stiletto pumps, and a dark brown handbag.

31) All about the Accessories

Trendy woman in cream turtleneck sweater dress, brown hat and olive green boots

Look like an A-list fashionista in cream-colored wool (photo: myshowroomblog.es)

Even if you’re not an A-list style star, who says you can’t still dress like one? This look could be straight from the pages of a fashion magazine and is super easy to achieve yourself. The basis of the outfit is a cable knit woolen sweater dress in cream pulled up at the sleeves. Add olive green over-the-knee boots and you’ve got a sophisticated winter must-try ensemble. The accessories really bring this look alive: round-rimmed dark sunglasses, a wide-brimmed camel-colored hat, and fine gold jewelry.

32) Contemporary Classic

Trendy brunette in navy blue sweater dress and black thigh-high boots

Combine your finest contemporary pieces for a modern look (photo: jessannkirby.com)

This ensemble is designed for trendsetters. Truly embracing the best of contemporary style, this outfit is made up of winter staples paired together in a modern, trendy way. The upper thighs may be on show with this mini woolen sweater dress, but this is balanced out with a high crew neck line as well as long sleeves. We love the quirky, unexpected touch of a collared shirt peeking out underneath, while long suede black boots tie it all together beautifully.

33) Style on Standby

Stylish brunette in grey woolen turtleneck dress and black suede boots

A woolen dress and thigh-high boots as your go-to outfit (photo: thedarlingdetail.com)

Stuck on something to wear in the chilly winter weather? With a pair of boots and a woolen dress, you’re always set to go. This outfit of a gray woolen turtleneck dress paired with thigh-high boots is both trendy and chic. Best of all, you can dress this ensemble up or down, casual or sophisticated – all depending on the accessories you choose to style it with. In this instance, the effect is simple and laidback, ideal for a casual day of shopping or sightseeing.

34) All Black Aesthetic

Chic brunette in black turtleneck woolen dress and black suede boots
A sexy sliver of skin adds magic to this all-black ensemble (photo: blankitinerary.com)

Don’t be scared to go a little dark this season. In fact, it’s the monochrome effect of all black that creates the true magic in this outfit. Of course, this turtleneck sweater dress is chic and trendy. But it’s actually the little patch of skin on the thighs that creates all the contrast in this ensemble. Over-the-knee boots in black suede are a modern touch that truly polishes off the look.

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