20 Ultra-Preppy Looks to Beat Those Winter Blues

1. The Violette Short-Sleeve Tinsel Sweater by Maeve

With 'tinsel' literally in this sweater's name, you'll be making a shiny statement wherever you wear this piece. It also comes in silver, gold, navy blue, and brown to suit your personal holiday style.

2. The A&F Madeline Crew Sweater

This femme 'fit boasts a bow that's reminiscent of holiday gifts and all things merry. It only helps that this sweater is super soft to the touch!

3. Out From Under Catching Feelings Fairisle Print Cropped Pullover

This sweet holiday sweater has an adorable reindeer design along the front, so it's instantly going to fit in for any holiday party. You can also snag the pair of matching shorts to complete the coziness if you'd rather stay in.

4. BDG Stella Star Graphic Oversized Pullover Sweater

With this sweater, you'll literally be a star. The color palette challenges holiday tradition in the best way, though you could totally make it a better fit for a party with a black mini skirt, tights, and metallic boots.

5. Maeve Faux-Fur Collar Cropped Cardigan Sweater

Oh, so fancy! This cardi's collar is lined with faux fur to make it feel ultra-luxe. Layer it over your best party dress, and voila!

6. ASTR the Label Velvet Bow Cardigan

Bring on more bows, please! This tie-up cardigan secures with two oversized velvet bows that speak to the holiday season flawlessly.

7. Gap Factory Peanuts Relaxed Gap Logo Sweatshirt

Snoopy is truly a holiday icon, especially in his dramatic puffer jacket. Don the famous dog on this cozy sweatshirt – it's so much cuter than an ugly Christmas sweater, plus you'll earn mega compliments (everyone loves Snoop!) wearing it.

8. Free People Festive Frost Sweater

This fuzzy sweater is downright festive, thanks to the traditional stripes across the top half. We love it because it still leans very 'holiday,' but isn't explicitly so, since the color palette isn't just reds and greens.

9. Vinyl Icons Martini Embellished Off The Shoulder Graphic Fleece Sweatshirt

Espresso martinis are a hallmark of the holiday season, and you simply can't change our minds on that. Get playful with your holiday sweater selection with this design that evokes a happy hour at any time of day, especially on a holiday break away from school or work!

10. We The Free Flower Patch Sweater

You'll be able to get a lot of wear out of this sweet red sweater around the holidays! The slouchy fit is ideal for pairing with even more winter layers to stay warm.

11. American Eagle Whoa So Soft Oversized Grinch Holiday Sweater

With Christmas' favorite villain on it, this super-soft sweater will always be in style around the holidays.

1. Slouchy Boots

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Take a page from Charli XCX's style book with some slouchy boots this winter. This shoe trend has roots that go back to the '80s, but you can absolutely rock them with some modern flair.

Banana Republic Factory Vegan Tall Slouch Boots

A sleek black pair of boots like these are easily wearable with everything from maxi skirts and dresses, to jeans and jorts. I like that the slouch here is a bit more understated, though you can definitely find styles that are way more exaggerated. Jennifer Lopez recently rocked a statement trench coat with her slouchy boots, and the look's living in my head rent-free.

Free People Extra Slouch Boots

Remember what I said about exaggerated? This is what I was talkin' about. These suede boots from Free People embrace folds on folds, bringing an interesting bit of texture to this boho-leaning look. The pointed toe and stitch work throughout also give this pair some nice Western flair.

Steve Madden Smith Red Leather Boots

Another fun iteration of slouchy boots you can wear this winter is the foldover boot. Though smoother, you still get quite the unique silhouette! These red boots were simply made to be seen.

2. Tall Moto Boots

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Moto boots are the winter shoe trend to snag if you like your outfits to have a some edge. What sets them apart from a regular ol' boot is typically the hardware visible on the sides and a chunky heel that can withstand wear.

Maguire Lucca Boots

These are extremely reminiscent of the famous Frye Campus boots, especially in color. The harness gives them a good biker edge, though you can also choose to remove it based on your mood. Since most moto boots hit right under the knee, they work just as well with mini dresses as they do wide-leg jeans.

Ash Trinidad Boots

Black pairs with everything, plus the darker color adds a good amount of mystery to any moto-inspired winter look. I'd rock these with some vintage jeans and a warm, chunky sweater. Bonus points for a vampy makeup look.

Steve Madden Ruskin Chestnut Suede Boots

Suede is undoubtedly one of the main stars in this winter's shoe trends, no matter what kind of shoe it's featured on. The more you wear these, the more character the suede takes on. It's a win-win.

3. Pointy Flats

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Let's get straight to the point: pointed toes are in. They're perfectly fierce and feisty – I think they're the ultimate style for happy hours or nights out with the gals. You can shop all kinds of shoes with pointed toes, like boots, booties, and kitten heels, but pointy ballet flats are truly where it's at if your main consideration is comfort.

Linea Paolo Noella Flats

The lace-up bow styling and dotted trim on these flats give 'em the cutest coquette vibe.

Jeffrey Campbell Lilly Buckle Slingback Flats

For an edgier take, these slingback flats boast some real eye-catching buckles. Pair them with some baggy jeans, a basic tee, and a chore jacket to totally nail all of this year's fashion trends.

Jeffrey Campbell Pistil Pointed Toe Flats

These flats are iconic not only in shape, but in color, too. Brighten up the drab winter season with this playful burst of yellow! I promise you won't regret it.

4. Platform Mocaasins

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You have the Clarks Wallabees to thank for the resurgence of moccasins this season. I personally adore them for their standout silhouette, and it's only a bonus that they're uber-comfortable for the cold temps! Moccasins come in many different styles across the brands we love, listed below.

Clarks Wallabee Boots

These booties are perfect for laid-back winter outings. Pop on a pair of jeans and your go-to cold weather layers, and you're ready to conquer anything – in style.

SeaVees Hayward Platforms

The contrast between these shoes' upper and lower halves is so cute to me. They were purposefully designed to be part-sneaker, part-loafer, so you can easily dress them up or down based on the day.

UGG Women's Disquette Alpine Slippers

Though more of a slipper, these UGGs still retain a ton of classic moccasin details. The laces and stitching are a dead giveaway, plus you get to enjoy the comfort of a slipper (thanks to the lining) without them wearing out super quick (just look at that thick outsole)!

5. Burgundy Loafers

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Burgundy (AKA dark cherry red) proved to be one of 2024's hottest colors across all sectors of fashion. Thus, it's no surprise that it's been creeping its way towards footwear! Burgundy is quite the sophisticated color, finding its match with an equally sophisticated shoe style: loafers.

Mia Amore Hali Penny Loafers

Though more polished, you can still wear loafers casually with jeans and graphic tees. I think they look best when you have a basic sock on, too.

Dr. Martens Adrian Snaffle Pebble Grain Leather Kiltie Loafers

The burgundy color trend also gives you the perfect opportunity to work in a pop of color to your wardrobe without going too bold, if you're not really ready to invest in brights (or if they're just simply not your thing).

Steve Madden Madison Burgundy Box Leather Loafers

You can literally put some prep in your step with these classic leather loafers.

6. Fur-Lined

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Peeps of fur (or preferably, faux fur) are this winter's final prominent shoe trend, mostly thanks to the UGG brand's signature faux sheepskin lining. These styles are undeniably cozy and functional for providing all the warmth your feet need this season.

UGG Classic Chillapeak Boots

Boosted with furry texture and height from the platform soles, these UGGs are perfect for wearing aprés ski or just on those bone-chilling cold days in the city.

Tommy Hilfiger Lined Lace-Up Snow Boots

These lined boots were specifically made to stand up to snow, but still look so stylish. I love the crossing laces and suede paneling on the sides that make them feel more a tad more upscale!

UGG New Heights Genuine Shearling Cuffable Boots

You can wear these rolled up or cuffed down to show off more of the soft shearling lining. I love that these UGGs push past the brand's typical look with a funky curved footbed and chunky sole.

Talking to Vanity Fair for her newest film Lee, Kate Winslet revealed one project she wishes fans asked about more is Iris. The 2001 film stars Kate as a young Iris Murdoch against Judi Dench's older counterpart. And for Kate, nothing was more terrifying than working with such a wonderful actress.

"People don’t really ask me about Iris. It’s such a delicate film," she says. "It was the first thing I had done after having my daughter. Going to work with a baby, I’m playing Iris Murdoch, looking to Judi Dench’s older Iris Murdoch — I was sh—ting myself."

Considering how nervous I get when I meet my heroes, I can only imagine what it was like to meet Dame Judi Dench. Talk about a dream! Another film Kate loves is Revolutionary Road, and not just because she got to reunite with Leonardo DiCaprio.

"The thing that people say is, 'You got to work with Leo again.' Then they go off on the whole Leo tangent, which I totally understand," she says of the film, which follows an ambitious couple who find themselves trapped in the reality of 1950s suburbia. "But Revolutionary Road — f—king hell, it just knocked us all sideways. Unbelievably difficult material. I was very proud of that film and what Leo and I were able to create as Frank and April. It was so brutal."

The process for getting Lee into the world sounds equally brutal, considering Kate started working on it over a decade ago. As producer, Kate tells Vanity Fair she doesn't mind the fact she's done more for the film than if she only had an acting credit. "That has felt very necessary for this film. But it’s also just really important to me," she says. "It’s important to me that people know that it’s out there and might feel compelled to go and see it."

Because it turns out, commercial success or stardom on its own doesn't actually help your movie get made! "It doesn’t matter who you are," she says. "No one’s going to go, 'Oh, I’ll just back that pony because she was in Titanic.' It doesn’t happen that way, and I never expected that. That’s really important to say."

"I've gotten older and I’ve learned more and felt more confident in myself about whether or not I could actually do it," she adds. "It’s not something I would’ve done had I not felt so passionately about the subject, and Lee was just—she wouldn’t let me go."