Slay Winter with 29 Early Winter Fashion Outfits

Brace yourselves, fashion lovers! Early winter doesn’t have to mean sacrificing style for warmth. We’ve curated 29 killer outfits that prove you can look utterly fabulous while staying cozy, no matter how chilly it gets. Get ready to upgrade your wardrobe with these effortlessly chic looks!

1. The “I Woke Up Like This” Oversized Sweater & Leather Look

This outfit screams cool-girl chic without even trying. It’s the perfect blend of cozy comfort and edgy style, making it ideal for those days when you want to look put-together but feel like you’re wrapped in a blanket.

Outfit Pieces:

Oversized chunky knit sweater (think cream, charcoal, or forest green)
Faux leather leggings or slim-fit leather pants
Chunky-soled ankle boots
Crossbody bag

Styling Tips:

Balance the volume of the sweater with the sleekness of the leather leggings. A half-tuck of the sweater front can define your waist without losing that relaxed vibe.

This look is your go-to for casual coffee dates, shopping sprees, or even a relaxed evening out with friends. Add a simple gold chain necklace for a touch of sparkle.

2. The Elevated Puffer Vest & Knit Dress Combo

Who says puffers can’t be chic? This outfit takes your favorite comfy knit dress and elevates it with a stylish puffer vest. It’s practical, warm, and surprisingly sophisticated.

Outfit Pieces:

Long-sleeve knit midi dress (ribbed texture works wonders!)
Quilted puffer vest (in a contrasting or complementary color)
Knee-high boots or sleek ankle boots
Beanie hat (optional, but highly recommended for extra warmth)

Styling Tips:

Choose a knit dress that skims your figure without being too tight. The vest adds an extra layer of warmth and visual interest, breaking up the silhouette of the dress.

Perfect for brisk walks, weekend errands, or even a casual lunch. Swap the beanie for a silk scarf tied around your neck for a different vibe.

3. The Classic Camel Coat & Denim Duo

A camel coat is a timeless early winter essential, and pairing it with denim is pure genius. This outfit is sophisticated yet effortless, making it a true wardrobe staple.

Outfit Pieces:

Classic camel wool coat
Straight-leg blue jeans
White crisp button-down shirt or a fine-knit sweater
Leather loafers or pointed-toe ankle boots

Styling Tips:

Ensure your jeans are well-fitting and the coat hits at a flattering length, typically mid-thigh or knee-length. Roll up the cuffs of your shirt slightly if wearing under a sweater for a peek of crisp white.

This look is perfect for work meetings, smart-casual events, or just feeling polished on a daily basis. Add a statement belt over the coat for an hourglass silhouette.

4. The “Business Casual, But Make It Cozy” Skirt Outfit

Who said office wear has to be boring? This look blends professional polish with undeniable warmth, making it perfect for those chilly commutes.

Outfit Pieces:

Pleated midi skirt (wool or a heavier fabric)
Fine-gauge turtleneck sweater
Tall shaft boots (that disappear under the skirt hem)
Structured tote bag

Styling Tips:

Tuck the turtleneck neatly into the skirt to define your waist. The boots should be sleek enough not to add bulk under the skirt, creating a long, elegant line.

Ideal for the office, client lunches, or any semi-formal early winter event. Layer a tailored blazer over this for extra warmth and professionalism.

5. The Weekend Warrior Flannel & Leggings Look

When comfort is king, but you still want to look cute for your weekend adventures, this is your go-to. It’s relaxed, warm, and totally Instagram-worthy.

Outfit Pieces:

Oversized flannel shirt (classic plaid or a solid color)
High-waisted black leggings
Sneakers (chunky white or classic black)
Baseball cap (optional, for that extra casual vibe)

Styling Tips:

Wear the flannel open over a simple tee or tank, or button it up and tie it at the waist for a different silhouette. Leggings should be thick and squat-proof, FYI!

Perfect for running errands, grabbing brunch, or a casual day out. Throw on a denim jacket if it gets extra chilly.

6. The Monochromatic Magic Sweater & Trousers

Effortlessly chic and incredibly flattering, a monochromatic outfit always looks expensive. This early winter version focuses on texture and subtle variations in tone.

Outfit Pieces:

Chunky knit sweater (in a neutral like beige, gray, or cream)
Wide-leg trousers (in a matching or slightly darker shade of your neutral)
Ankle boots (matching the trousers for an elongated look)
Delicate gold jewelry

Styling Tips:

Play with textures! A ribbed sweater with smooth wool trousers adds depth. Ensure the trousers are long enough to just skim the top of your boots.

This outfit is versatile enough for work, dinner, or a stylish weekend outing. Add a long scarf in a complementary print for a pop of personality.

7. The Edgy Knit Dress & Combat Boots

Combine feminine grace with a touch of rebellion. A cozy knit dress gets an instant cool factor when paired with rugged combat boots. Seriously, it’s a vibe.

Outfit Pieces:

Ribbed knit midi dress (fitted or slightly relaxed)
Lace-up combat boots
Leather jacket
Small black backpack or shoulder bag

Styling Tips:

Choose a dress that’s comfortable for layering. The leather jacket adds an extra layer of warmth and edge, tying the whole look together. Don’t be afraid to mix textures!

Great for concerts, casual nights out, or just embracing your inner rockstar. Add some fishnet tights under the dress for an even bolder statement.

8. The Cozy Cardigan & Wide-Leg Jeans

Forget your grandma’s cardigan; this is a modern, stylish take on a classic. It’s the perfect blend of relaxed and put-together, ideal for those transitional early winter days.

Outfit Pieces:

Chunky knit cardigan (oversized and long)
High-waisted wide-leg jeans
Fitted basic tee or tank top
Platform sneakers or block-heel ankle boots

Styling Tips:

Leave the cardigan open to show off your top, or belt it at the waist for a more defined silhouette. Ensure your jeans are long enough to avoid looking cropped with your chosen footwear.

A fantastic option for weekend outings, casual meetups, or working from home in style. Layer a delicate necklace for a subtle sparkle.

9. The Sporty Chic Tracksuit & Tailored Coat

Who says comfort can’t be chic? Elevate your favorite cozy tracksuit by throwing a sophisticated tailored coat over it. It’s the ultimate high-low fashion statement.

Outfit Pieces:

Matching tracksuit set (hoodie and joggers, in a solid neutral)
Long tailored wool coat (black, gray, or camel)
Clean white sneakers
Baseball cap or simple beanie

Styling Tips:

The key here is contrast: the relaxed tracksuit against the sharp lines of the coat. Make sure your tracksuit is well-fitting and not too baggy for a polished look.

Perfect for travel, running errands, or simply looking stylish on a casual day. Add a simple gold hoop earring to complete the look.

10. The Sweater Vest & Collared Shirt Combo

Bring back a retro favorite with a modern twist! The sweater vest layered over a collared shirt is preppy, polished, and perfectly early winter appropriate.

Outfit Pieces:

Oversized sweater vest (cable knit or argyle)
Crisp white button-down shirt
Tailored trousers (straight-leg or wide-leg)
Loafers or block-heel boots

Styling Tips:

Let the collar and cuffs of the shirt peek out from under the vest. For an extra touch, add a delicate necklace over the vest or a tie for a truly academic vibe.

Ideal for work, school, or a smart-casual brunch. This look is super versatile and can be dressed up or down with accessories.

11. The Velvet Dress & Ankle Boots for Night

Early winter evenings call for luxurious textures! A velvet dress is instantly festive and chic, perfect for holiday gatherings or a special night out.

Outfit Pieces:

Velvet midi or mini dress (jewel tone like emerald, sapphire, or deep red)
Sleek black ankle boots (with a block heel)
Faux fur coat or tailored blazer
Clutch bag

Styling Tips:

Let the velvet be the star! Keep accessories minimal and elegant. Tights are a must for warmth if you’re wearing a mini dress.

Perfect for holiday parties, dinner dates, or any event where you want to feel a little extra glamorous. A bold lip color completes this sophisticated ensemble.

12. The Layered Turtleneck & Slip Dress Dream

Extend the life of your favorite slip dress by layering it over a cozy turtleneck. This ’90s-inspired look is surprisingly warm and incredibly chic for early winter.

Outfit Pieces:

Silk or satin slip dress
Fine-knit turtleneck sweater (black, cream, or a complementary color)
Knee-high boots
Dainty layered necklaces

Styling Tips:

Ensure the turtleneck is thin enough not to create bulk under the dress. The boots should be tall enough to meet the hem of the dress, creating a seamless look.

Great for a stylish dinner, a gallery visit, or a sophisticated night out. Add a tailored coat for extra warmth and polish.

13. The Statement Scarf & Classic Denim

Sometimes, all it takes is one killer accessory to transform an outfit. A bold, statement scarf can elevate simple jeans and a sweater into a fashion moment.

Outfit Pieces:

Chunky knit sweater (solid neutral)
Straight-leg or skinny jeans
Oversized patterned or colorful scarf
Ankle boots or stylish sneakers

Styling Tips:

Tie the scarf in a simple knot or wrap it loosely for maximum impact. Let the scarf be the focal point, keeping other accessories minimal.

This is your go-to for casual outings, weekend adventures, or adding personality to an otherwise simple look. A warm beanie in a complementary color would also be fab.

14. The Corduroy Pants & Shearling Jacket Vibe

Embrace retro textures with this cozy yet stylish early winter combo. Corduroy offers warmth and a cool vintage feel, perfectly complemented by a plush shearling jacket.

Outfit Pieces:

High-waisted corduroy pants (wide-leg or straight-leg, in a rich color like rust or forest green)
Simple knit sweater or long-sleeve tee
Faux shearling jacket
Chelsea boots

Styling Tips:

Ensure the corduroy pants fit well – not too tight, not too baggy. The shearling jacket adds a touch of rugged charm and serious warmth. Try a French tuck with your sweater.

Perfect for a casual weekend, outdoor market visits, or a relaxed get-together with friends. A simple beanie can complete this laid-back look.

15. The “Power Dressing” Plaid Blazer & Jeans

Take your favorite casual denim up a notch with a sophisticated plaid blazer. This outfit is smart, stylish, and perfect for looking polished without being overdressed.

Outfit Pieces:

Plaid oversized blazer
Dark wash straight-leg jeans
Basic white tee or fine-knit turtleneck
Heeled ankle boots or loafers

Styling Tips:

Roll up the blazer sleeves slightly for a relaxed, effortless look. The blazer should be slightly oversized for that modern, chic vibe. Add a belt to cinch it if you prefer.

Ideal for casual Fridays, smart-casual events, or a stylish brunch. Layer with delicate necklaces to add a feminine touch.

16. The Sweater Dress & Over-the-Knee Boots

This combo is pure early winter magic: cozy, chic, and undeniably sexy. A sweater dress paired with over-the-knee boots creates an elegant and warm silhouette.

Outfit Pieces:

Knit sweater dress (mini or midi length)
Over-the-knee boots (suede or leather)
Tights (if wearing a mini dress)
Long tailored coat or faux fur vest

Styling Tips:

Ensure there’s a small gap between the top of your boots and the hem of your dress for maximum impact. The sweater dress should be comfortable but not overly baggy.

Perfect for dinner dates, holiday parties, or any occasion where you want to feel effortlessly glamorous. Add a statement belt to cinch the waist of the dress.

17. The Utility Jumpsuit & Cozy Knit

A utility jumpsuit is a fantastic one-and-done outfit, and for early winter, layer a chunky knit underneath for warmth and style. It’s practical, trendy, and super cool.

Outfit Pieces:

Utility jumpsuit (cotton or denim, in army green, black, or tan)
Chunky knit turtleneck or crewneck sweater
Chunky sneakers or combat boots
Beanie hat

Styling Tips:

Leave the top few buttons of the jumpsuit undone to show off the sweater. Roll up the cuffs of the jumpsuit to expose your footwear. Cinch the waist with a belt!

Great for creative workdays, casual outings, or just looking effortlessly cool. Add a simple gold chain for a touch of bling.

18. The “Pop of Color” Sweater & Dark Jeans

Early winter doesn’t have to be all neutrals! Inject some joy into your wardrobe with a vibrant pop of color sweater. It’s an instant mood booster, trust me.

Outfit Pieces:

Brightly colored chunky knit sweater (think fuchsia, cobalt blue, or emerald green)
Dark wash skinny or straight-leg jeans
Black ankle boots
Simple stud earrings

Styling Tips:

Let the sweater be the star! Keep the rest of the outfit simple and neutral to let that color shine. A half-tuck of the sweater front works wonders.

Perfect for brightening up any casual day, from running errands to meeting friends for coffee. Add a matching lip color for extra impact.

19. The Leather Skirt & Chunky Cardigan

Combine the edgy appeal of a leather skirt with the cozy comfort of a chunky cardigan for a balanced and stylish early winter look. It’s versatile and chic.

Outfit Pieces:

Faux leather mini or midi skirt (A-line or pencil style)
Chunky knit cardigan (oversized, worn buttoned or open)
Tights (opaque black)
Ankle boots or knee-high boots

Styling Tips:

If wearing a mini skirt, opaque tights are a must for warmth and style. Cinch the cardigan with a belt over the skirt for a more defined waist.

Ideal for a casual dinner, a night out, or even a stylish workday. Add a simple camisole or fine-knit top underneath the cardigan.

20. The Quilted Jacket & Denim Skirt

A practical yet stylish combo for those milder early winter days. The quilted jacket offers warmth without bulk, while a denim skirt keeps things casual and cool.

Outfit Pieces:

Quilted jacket (short or medium length, in olive green or navy)
Denim midi skirt
Striped long-sleeve top
Chelsea boots or stylish sneakers

Styling Tips:

Tuck the striped top into the skirt to define your waist. The quilted jacket adds a country-chic vibe that’s perfect for casual outings.

Great for weekend adventures, casual brunches, or a stroll through town. Add a simple crossbody bag for practicality.

21. The “All Black Everything” But With Texture

An all-black outfit is always chic, but for early winter, play with textures to make it truly stand out. It’s sophisticated, slimming, and incredibly versatile.

Outfit Pieces:

Black chunky knit sweater
Black faux leather pants or coated jeans
Black suede ankle boots
Black tailored wool coat

Styling Tips:

Mix matte and shiny textures for depth – think a matte knit with glossy leather. Different shades of black can also add subtle interest. A half-tuck of the sweater works wonders.

Perfect for literally any occasion, from a casual day to a chic evening out. Add a silver or gold statement necklace to break up the monochrome.

22. The Vest & Hoodie Layering Trick

For ultimate warmth and a sporty casual vibe, layer a vest over a hoodie. This outfit is practical for outdoor activities but still looks stylish enough for everyday wear.

Outfit Pieces:

Puffer vest (in a bold color or classic black)
Oversized hoodie (in a contrasting or complementary color)
Joggers or comfortable jeans
Sneakers

Styling Tips:

Ensure the hoodie isn’t too bulky under the vest. The vest should fit comfortably over the hoodie without feeling restrictive. Pull the hoodie strings for a casual touch.

Ideal for brisk walks, running errands, or just lounging in style. A baseball cap can complete this laid-back look.

23. The Long Cardigan & Mini Dress

Keep your favorite mini dress in rotation by pairing it with a super long, cozy cardigan. It adds warmth and creates an interesting layered silhouette.

Outfit Pieces:

Long-sleeve mini dress (knit or a thicker fabric)
Extra-long knit cardigan (duster length)
Opaque black tights
Ankle boots or knee-high boots

Styling Tips:

The cardigan should be significantly longer than the dress for a dramatic effect. Keep the cardigan open to show off the dress underneath. Belt it for a different look.

Great for casual gatherings, a stylish day out, or even a relaxed evening. Add a chunky scarf for extra warmth and texture.

24. The Fair Isle Sweater & Classic Trousers

Embrace the festive spirit with a beautiful Fair Isle sweater. Pair it with tailored trousers for a polished yet cozy early winter look that’s perfect for any casual holiday event.

Outfit Pieces:

Fair Isle knit sweater
Tailored wool trousers (black, gray, or navy)
Chelsea boots or loafers
Simple stud earrings

Styling Tips:

Let the intricate pattern of the Fair Isle sweater be the star. Tuck it in or wear it untucked, depending on the length and your preference. The trousers should be well-fitting.

Perfect for family gatherings, holiday brunches, or a cozy day out. Layer a simple long-sleeve tee underneath for extra warmth.

25. The Trench Coat & Hoodie Surprise

Yes, you can wear a trench coat in early winter! Layer it over a hoodie for an unexpected twist that’s both stylish and practical. It’s a high-low fashion moment.

Outfit Pieces:

Classic trench coat
Hoodie (gray or black works best)
Straight-leg jeans
Chunky sneakers

Styling Tips:

Pop the hood out over the trench coat collar for a cool, casual vibe. Roll up the trench sleeves slightly to reveal the hoodie cuffs. This look is all about unexpected layering.

Ideal for city exploring, casual workdays, or adding an edge to your everyday style. Add a pair of dark sunglasses for ultimate coolness.

26. The Sweater & Pleated Skirt Combo

A match made in early winter heaven! A cozy sweater paired with a flowing pleated skirt is elegant, comfortable, and perfect for a variety of occasions.

Outfit Pieces:

Chunky knit sweater (tucked in or half-tucked)
Satin or wool pleated midi skirt
Heeled ankle boots
Statement earrings

Styling Tips:

Tuck the sweater into the skirt to emphasize your waist and the skirt’s flow. Choose a skirt in a rich color or subtle print to add interest. The boots should be sleek.

Great for dinner, a holiday gathering, or a stylish day at the office. Layer a tailored coat over it for extra warmth.

27. The Shacket & Black Jeans for Effortless Cool

The shacket (shirt jacket) is your early winter layering hero. Pair it with black jeans for an effortlessly cool and comfortable look that’s perfect for everyday wear.

Outfit Pieces:

Oversized shacket (wool blend or heavy flannel)
Fitted basic tee or thin knit top
Black skinny or straight-leg jeans
Combat boots or chunky sneakers

Styling Tips:

Wear the shacket open over your top for a relaxed vibe. Roll up the sleeves slightly for a casual touch. The key is an oversized, relaxed fit for the shacket.

Perfect for casual outings, running errands, or a relaxed weekend. Add a simple beanie for extra warmth and style.

28. The Turtleneck & Pinafore Dress Revival

Bring back the playful charm of a pinafore dress by layering it over a warm turtleneck. It’s a cute, preppy, and surprisingly sophisticated early winter option.

Outfit Pieces:

Wool or corduroy pinafore dress
Fine-knit turtleneck sweater
Opaque black tights
Loafers or block-heel ankle boots

Styling Tips:

Ensure the turtleneck is sleek enough not to create bulk under the dress. The tights are essential for warmth and to complete the polished look.

Ideal for a creative workday, a casual meet-up, or a stylish weekend outing. Add a long pendant necklace to draw the eye down.

29. The Cozy Leggings & Long Shirt & Vest Trio

For those days when ultimate comfort is non-negotiable but you still want to look presentable, this layered trio is your best friend. It’s warm, soft, and totally chic.

Outfit Pieces:

Thick, high-waisted leggings
Long button-down shirt (oversized, worn open or partially buttoned)
Puffer vest or fleece vest
Sneakers or UGG-style boots

Styling Tips:

Layer the long shirt over a simple tee, then add the vest for warmth. The length of the shirt should cover your bum for a flattering look with leggings. Seriously, this combo is amazing.

Perfect for travel, lounging at home, or running quick errands. A beanie and a large tote bag complete this effortlessly comfortable ensemble.

There you have it, 29 ways to absolutely slay early winter fashion! Don’t let the dropping temperatures cramp your style. Go forth, experiment, and make these chilly days your most fashionable yet!