We’ve got a few months of winter left, so I thought I’d share some of my favorite winter outfits for trading now to give you some ideas for building outfits for cold weather. I get asked all the time how to stay stylish while bundled up, so I’ve put together my ultimate guide. And don’t worry I’ve included a shopping guide at the bottom with all my current shopping favorites!
My Winter Outfits Ideas Style Rules
In the winter, I tend to lean more toward neutrals than usual. My winter coats do a lot of the work when it comes to putting outfits together. Since we’re all bundled up, I rely on accessories to make an impact and add personality to each look. I’ve found that investing in quality basics and statement coats has made winter dressing so much easier—it’s all about having those key pieces you can mix and match forever.
Weekend Athleisure
This is my weekend uniform – you’ll see me wearing this combo for coffee runs, grabbing bagels in the neighborhood, or going for walks with friends. Here’s how I put it together:
- Start with your favorite high-quality leggings (I swear by Lululemon Align pants
- Add a cozy, oversized sweater or sweatshirt
- Slip on some comfy walking shoes (I rotate between New Balance and Nike
- Top with a beanie for warmth (and to hide bad hair days.
- Top with a great coat
On super cold days, I’ll swap in a puffer coat for maximum warmth. My current favorite is from Aritzia—their Super Puff is seriously worth the investment. I’ve had mine for three winters now, and it still looks brand new.
Everyday Elegance: Trousers + Sneakers
For everyday winter looks, I always reach for my favorite trousers. While I like to pair them with ballet flats, sneakers are my most worn combo for running around the city. Here’s how I style this look:
- Choose well-cut trousers in neutral colors (black, navy, or camel are my go-to’s)
- Add a fitted turtleneck or chunky sweater
- White sneakers keep it fresh
- Layer with a long wool coat
- Add delicate jewelry to dress up the sneakers
This is perfect for many occasions, from client meetings to weekend brunches. It’s the perfect combination of polished and practical.
Leather Pants: Your Winter Workhorse
My faux leather pants are my winter workhorses! I wear them 3-4 times a week during the cold months. Here’s how I style them for different occasions:
For Day:
- Pair with chunky sneakers
- Add an oversized cashmere sweater
- Layer with a blazer or casual jacket
- Keep accessories minimal
For Night:
- Switch to heeled booties
- Try a silk blouse or fitted turtleneck
- Add statement jewelry
- Top with a sleek coat
The contrast of casual shoes with the elevated leather is so cool for daytime, while the evening styling is totally polished.
How to Mix Neutrals
Winter is when my neutral mixing skills really come out to play. Here’s my formula for neutral mixing 101:
- Start with ivory or cream
- Add camel or tan
- Add black for the definition
- Use gray as a softener
- Mix different textures within the same color family
Some of my favorite neutral combos:
- Cream sweater + camel coat + black boots
- Gray turtleneck + ivory coat + black pants
- All black with camel accessories
- Mixed grays with ivory accents
It’s always cozy and warm but still looks put together. The key is to mix textures – smooth leather with chunky knits and soft wool with textured cashmere.
Riding Boots 101
Nothing beats a good pair of riding boots with a simple wrap coat on super cold days. This combo has been my go-to for years, and here’s how I keep it looking fresh:
- Choose boots with minimal hardware
- Pair with slim jeans or leggings
- Add a long sweater or sweater dress
- Belt your wrap coat to create the shape
- Layer necklaces for interest
Pro tip: weather-proof your leather boots at the beginning of the season. It will greatly extend their lifespan!
The Sweater Dress Formula
Sweater dresses are my go-to for dressier winter events. Here’s my formula for styling them:
For Day:
- Choose a midi length
- Add knee-high boots
- Layer with a long coat
- Add delicate jewelry
- Consider a belt to define the waist
For Night:
- Go for a fitted silhouette
- Style with over-the-knee boots
- Add statement earrings
- Choose a shorter coat to show the dress length
- Consider sheer tights for extra warmth
Quick style tip: If you need more inspiration on how to wear sweater dresses, check out my full guide. There are so many ways to get it wrong, but when done right, they’re amazing!
Plaid is My Jam
A plaid one is the perfect solution when I’m feeling meh about my neutral coats. The Abercrombie Dad Coat comes in great plaid options – I’ve had mine for two seasons now, and it still gets compliments. Here’s how I style it:
For Casual Days:
- Black high-rise jeans (Agolde are my fave)
- Simple white or cream sweater
- Chelsea boots or ankle booties
- Minimal jewelry to let the coat shine
- Add a beanie in the same color
For Work:
- Black trousers
- Fitted turtleneck in a solid color
- Pointed-toe boots
- Structured bag
- Simple gold jewelry
The key to wearing plaid is to keep the rest of your outfit simple and let the coat be the focus. To avoid pattern overload, I usually wear solid colors underneath.
Black & Gray
Another winter combo I love? Black and gray together. There’s something so elegant about this pairing that feels especially wintery. Here’s how I make it interesting:
Mix Your Textures:
- Cashmere gray sweater
- Black leather pants
- Suede boots
- Wool coat
- Add interest with different fabric finishes
Play with Proportions:
- Oversized gray knit
- Slim black pants
- Chunky boots
- Fitted coat
- Layer delicate necklaces for dimension
Cozy-Meets-Polished
I love contrast – like pairing a casual sherpa coat with dressier boots. The mix of textures and styles keeps it interesting. Here’s how I balance the look:
Casual Elements:
- Teddy coat or sherpa jacket
- Comfy jeans
- Simple white tee or thin sweater
- Casual crossbody bag
Polished Additions:
- Heeled boots or loafers
- Structured bag
- Gold jewelry
- Silk scarf
Minis for Winter
Don’t pack away your mini skirts! I love wearing mine with cozy knits and riding boots. Perfect for days when I have meetings but evening plans, too. The key is layering:
Essential Components:
- Mini skirt (wool or leather works best)
- Thick knit sweater
- High boots (riding or over-the-knee)
- Quality tights (I swear by Wolford)
- Optional: thin thermal shorts underneath
Styling Tips:
- Balance proportions with a chunky knit on top
- Boots hit just below or above the knee
- Layer with a long coat for extra warmth
- Thick tights in black or the same color
- Thermal layers on extra cold days
Midi Skirt Moment
If you prefer longer lengths, try a tea-length midi skirt in a thick knit. It’s such a winter winner. Here’s how to make it work:
For Maximum Style:
- Midi knit in a neutral color
- With a fitted sweater or bodysuit
- Ankle boots or knee-high boots
- A coat that hits below the skirt
- Belt at the waist for definition
Texture Combinations:
- Ribbed knit skirt
- Smooth merino wool sweater
- Leather boots
- Wool coat
- Mix textures
Dark Florals
While florals feel springy, choosing darker versions and topping them with a wool blazer makes them winter-worthy. Here’s my approach:
Choosing the Right Florals:
- Dark backgrounds (navy, black, deep green)
- Small to medium-scale prints work best
- Heavy fabrics like silk twill or crepe
- Avoid bright or tropical
Styling for Winter:
- Layer with a wool blazer
- Opaque tights
- Substantial boots
- Minimal accessories
- Turtleneck underneath for extra warmth
Practical But Cool: Boot Edition
My favorite lug sole boots have been a total lifesaver for wet winter days – they’re completely waterproof! I wear them with jeans that hit right at the boot top for the best proportions. Some tips:
Casual Cool:
- Straight-leg jeans
- Oversized sweater
- Lug sole boots (I love my Marc Fisher pair)
- Puffer coat
- Crossbody bag for hands-free
Elevated Edge:
- Black jeans
- Fitted turtleneck
- Same lug boots
- Wool coat
- Gold jewelry to dress it up
Striped Sweater Strategy
Want to add some visual interest to a winter outfit, especially under a coat? A striped sweater never goes wrong. I’m obsessed with La Ligne’s versions. Here’s how I style them:
Classic:
- Striped crew neck or turtleneck
- High-waisted jeans
- Ankle boots
- Camel coat
- Simple gold jewelry
Modern Mix:
- Oversized striped knit
- Leather pants
- White sneakers
- Statement coat
- Layer necklaces
French Chic
When it’s warm enough, I love mixing navy and black – leather pants with loafers and a navy jacket. It feels so French and timeless. Here’s my formula:
The Perfect Palette:
- Navy wool coat or blazer
- Black leather pants or trousers
- Loafers or ballet flats
- White or cream top
- Delicate gold jewelry
Additional styling:
- Clean lines and classic silhouettes
- No flashy hardware
- Quality fabrics
- Silk scarf for extra French-ness
- Red lip for polish
Winter Accessory Essentials
To make all these outfits work
- Good tights in different deniers
- Neutral colored scarves
- Leather gloves (tech-friendly and regular)
- Beanies and berets
- Structured bags that go with coats
- Water-resistant boots
- Warm socks (never underestimate good socks!)
Winter Care
To keep your winter pieces looking good:
- Get a fabric shaver for knits
- Waterproof leather boots at the beginning of the season
- Dry clean coats before storing
- Use shoe trees in boots
- Store sweaters folded, not hung
- Keep a lint roller nearby
- Consider cedar blocks for storage
