Preppy Winter Outfits

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Preppy Winter Outfits
How to Dress Preppy in the Winter

As much as I love warm weather, my passion for style encourages me to welcome winter with open arms. If you’re all about preppy style and want to learn more about how you can transition your wardrobe into the cold weather, I’ve got you covered. From cozy sweaters and winter boots to pom pom beanies and puffer jackets, I’ve provided several outfit ideas for different occasions, so that you can look perfectly preppy throughout the winter. 

Preppy Winter Outfits

Canada Goose Shelburne Review

Puffer Jacket With Jeans And High Boots

Canada Goose Shelburne Puffer Jacket / Sorel Boots (Sold out but similar HERE) / Rag & Bone Jeans (sold out but similar HERE) / Free People Scarf  (sold out but similar HERE) / BP. Sweater (Sold out but similar HERE)

This Shelburne Puffer Coat by Canada Goose is a must have for winter weather. It will keep you warm on even the coldest days. But unlike some of the other puffer coats I’ve tried, this one doesn’t make you sweat. Seriously, it’s amazing. Pair it with your favorite tall winter boots to keep your feet cozy in the snow, or easily swap the winter boots for rain boots. 

How to Style a Sweater Blazer - Work to Weekend

Sweater Blazer, Button Up Shirt, Jeans And Ballet Flats

White Ruffleneck Button-Up (Sold out but similar HERE) / Sweater Blazer / Demi-Boot Jeans / Black Reversible Tote Bag / Pearl Stud Earrings / Black Headband (Sold out but similar HERE) / Suede Ballet Flats (Sold out but similar HERE)

The sweater blazer is the piece that makes all the difference here. You can go straight from work to drinks with the girls without needing a wardrobe change. Wear the sweater over a preppy white button down, pull on your favorite pair of jeans, and slip into cute but comfortable ballet flats. A black tote bag, pearl earrings, and a black headband are the perfect accessories for this classy work to weekend outfit. 

How to Wear Dresses in Winter - Cashmere Tie Dress

Cashmere Collared Sweater Dress

Cashmere Collared Sweater Dress (Sold out but similar HERE) / White Topcoat (Sold out but similar HERE) / Tote Bag (Sold out but similar HERE) / Suede Ankle Boots / Pearl Hoop Earrings

What’s not to love about a gorgeous and luxuriously soft sweater dress? It’s the centerpiece of this winter outfit and proves that you can definitely wear dresses in the winter. The white topcoat adds another layer of warmth and elegance. Add a neutral tote bag, suede ankle boots, and pearl hoop earrings for the perfect outfit to wear out to dinner.

How to Wear Dresses in Winter - Black Crew

Black Crewneck Midi Sweater Dress With Sneakers

Black Crewneck Midi Sweater Dress (Sold out but similar HERE) / Suede Moto Jacket (Sold out but similar HERE) / Leather Tote Bag / Bar Stud Earrings / Black Sunglasses (Sold out but similar HERE) / Leather Sneakers

Speaking of wearing dresses in the winter, this is the perfect casual and cute outfit to wear while out and about on the weekend. The black midi sweater dress is long enough for cold temperatures and the suede moto jacket provides the perfect balance of warmth and style. I especially love styling a sweater dress with leather sneakers for a more laid-back look that is still super chic. 

Winter Vacation Outfit Ideas - Slopeside Style

Belted Puffer Jacket, Mock Neck Sweater, And Snow Boots

Fair Isle Mock Neck Sweater (Sold out but similar HERE) / Warm High Waisted Leggings (Sold out but similar HERE) / Belted Puffer Jacket (Low in stock but similar HERE) / Sunglasses (Sold out but similar HERE) / Pom Pom Beanie (Sold out but similar HERE) / Winter Snow Boots (Low in stock but similar HERE)

This is the perfect outfit for a weekend involving ski slopes or frolicking in the snow. Even in the coldest weather, you can still look chic and feel comfortable. Belted puffer jackets are great for staying warm without sacrificing style and I adore this crisp white one. The belt adds shape to your silhouette so you don’t disappear inside the coat. 

Underneath your coat, try a soft, cozy sweater and high waisted leggings. Put on a warm pair of socks and then slip your feet into these incredibly warm winter snow boots. Add a cute pom pom beanie and sunglasses and you’ll almost forget you’re surrounded by snow. 

How to Style Bean Boots

Half-Zip Sweater, Skinny Jeans, Long White Coat, And Bean Boots

Navy Half-Zip Sweater (Sold out but similar HERE) / High-Rise Skinny Jeans (Sold out but similar HERE) / White Coat (Sold out but similar HERE) / Earrings / Camp Socks / Shearling Lined Bean Boots

Bean boots are another cold weather essential. I like to wear skinny jeans with my bean boots because they are easiest to tuck into my socks or boots. For a classic look you can wear just about anywhere, add a half-zip sweater and a long white coat. Gold pearl hoop earrings are the perfect finishing touch. 

How to Style a Leather Puffer Jacket with a Striped Turtleneck

Vegan Leather Puffer Jacket, Striped Sweater, Demi-Boot Jeans, And Black Suede Boots

Leather Puffer Jacket (Low in stock similar HERE) / Striped Turtleneck Long-Sleeve Tee / Demi-Boot Jeans / Black Quilted Bag / Gold Bracelet / Pearl Huggie Hoop Earrings / Black Suede Boots

For a look you can wear from day to night, try pairing a vegan leather puffer jacket with a striped sweater and demi-boot jeans. If you thought regular leather jackets were warm, just wait until you try on a leather puffer jacket. It’s a whole new kind of cozy.

Finish the look with classic accessories like a black quilted bag and black suede boots, and you’re ready to hit the town in the middle of winter. 

How to Style a Sweater Dress with Knee-High Boots

Cream Sweater Dress With Houndstooth Wool Blazer And Knee High Black Suede Boots

Cream Sweater Dress / Houndstooth Wool Blazer / Leather Crossbody Bag / Knee-High Suede Black Boots (Low in stock similar HERE) / Silver Bracelet / Cubic Zirconia Stud Earrings

This outfit is perfect for date night. I love the way knee high boots look with this chic sweater dress. And the amazing gray houndstooth wool blazer adds a touch of sophistication to this gorgeous winter look. A leather crossbody bag matches perfectly, as does the silver jewelry. 

4 Valentines Day Outfits

Pink Sweater, Black Jeans, White Wrap Coat, And Winter Boots

Pink Mock Neck Sweater (Sold out but similar HERE) / Black Jeans / White Wrap Coat (Sold out but similar HERE) / Winter Boots / Red Crossbody Bag / Pearl Bow Earrings

This is another one of my favorite preppy winter date night outfits. The pink sweater is especially perfect for a Valentine’s Day dinner. Plus, the Ralph Lauren wrap coat and winter boots ensure you’ll stay warm when you’re walking to and from the car.

How to Style Veja Sneakers for winter

Black Mockneck Sweater, Jeans, Wool Parka, And Leather Sneakers

Sweater (Sold out but similar HERE) / Jeans (Sold out but similar HERE) / Coat (Sold out but similar HERE) / Bag / Mittens / Earrings / Veja Sneakers

This is one of my favorite winter outfits. You might know this already but I absolutely adore Veja sneakers. The Campo leather and suede sneakers have a chunky sole and somehow go great with just about anything. For this classic look, I styled the Veja Campo sneakers with a mock neck black sweater, a pair of demi-boot jeans, and an emerald green wool parka coat. A black crossbody bag, cute mittens, and pearl earrings complete the look. 

Easy cold winter outfits

Turtleneck Sweater, Warm Leggings, Snow Boots, And Puffer Coat

Sweater (Sold out but similar HERE) / Coat (Sold out but similar HERE) / Warm Leggings / Scarf (Sold out but similar HERE) / Hat (Sold out but similar HERE) / Mittens (Sold out but similar HERE) / Boots

Did someone say snow day? This outfit would be perfect for those cold winter days when the snowfall never seems to stop. The adorable, cozy sweater and warm winter leggings are perfect for staying comfortable around the house. Then when it’s time to head out, simply throw on your puffer coat, step into your snow boots, add your snow-day accessories and you’re ready. The snow is no match for you in this outfit. 

fall travel outfit idea

Turtleneck Sweater, Black Leggings, Bean Boots, And Plaid Scarf

Turtleneck Sweater (Sold out but similar HERE) / Leggings / Plaid Scarf / Sherpa Bean Boots / Socks / Bag / Sunglasses

I included this outfit as one of my go-to outfits for traveling because it’s one of the easiest winter or fall outfits to put together. It’s perfect for those cool days when you crave comfort above all else. I especially adore the plaid scarf because it adds another layer of warmth as well as a beautiful pop of color. 

Tips for Dressing Preppy in the Winter

How do you dress preppy in the winter?

Cozy sweaters are essential. 

Turtlenecks, mocknecks, rolled necks, and even sweater dresses; sweaters are arguably the most essential part of preppy winter style. Just be sure to stick with soft, smooth fabrics and avoid sweaters that are especially chunky or “furry.” True preppy style includes timeless knitwear that can be mixed and matched seamlessly.

When in doubt, accessorize with pearls.

It can be easy to forget about accessories when you’ve been adding layers of clothing to keep you warm in frigid temperatures. Whether it’s simple pearl earrings or a chic statement necklace, accessories are often exactly what you need to complete an outfit. 

Make your coat your statement piece.

If you truly want to dress preppy this winter, you should consider thinking of your winter coat as more of a statement piece. You may hang it up the minute you walk inside, but a gorgeous winter coat, whether in classic white or a striking color, is a must-have for preppy winter style. 

Boots elevate any winter outfit (Duck Boots, Bean Boots, Snow Boots, etc.)

A preppy winter wardrobe will have at least one pair of winter boots, and there’s a good chance they are either duck boots or Bean boots. I recommend having at least one other pair of winter boots on hand though. 

For added texture, style, and warmth, layer up.

Layers are important for warmth, but they also add an additional style element to your outfits. Whether you’re layering a sweater over a thermal, a coat over a sweater, or dress over tights, you can’t go wrong with layers.

Preppy Winter Outfits
Share your favorite preppy winter style essentials below!

I love discovering new ways to stay cozy and stylish in the winter. Feel free to share some of your favorite pieces! For more all things fashion and lifestyle, head on over to the blog.

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