The It-Girl’s Guide to Pairing Boots With Dresses This Fall

The best dress for girls who love a classic fall moment:

Ann Taylor Crew Neck Knit Dress

Classic fall outfits are always going to get us through the cooler season because they're effortless, like this striped knit dress. Using it as a base, you can add a lightweight trench coat for rainy days or a wool number when you need extra warmth. Next up, step into a pair of knee high boots and voilá! You'll have a low-fuss outfit that still looks chic.

The best dress for anyone who's tired of boring sweaters:

By Anthropologie Tulle Twofer Mini Dress

I've already added this dress to my wishlist because it's so pretty. I love anything that looks super feminine or frilly so this is one of those petite dresses I could wear every week if I had the chance. If you're on the hunt for anything that puts your other sweater dresses to shame, I highly recommend you buy this tulle mini dress!

For the girl who loves wearing colorful outfits:

Boden Ribbed Metallic Dress

The edit team at Brit + Co loves colorful pieces, which is why this metallic dress is beckoning to me. Besides the shimmery flecks, the expertly placed shades of hunter green, bubblegum pink, marigold, magenta, maroon, and cerulean blue are gorgeous.

I imagine this is something Ms. Frizzle would wear if she were in the modern world, and I mean that in the best way ever.

The best dress for the girl who loves a fun party moment:

Maeve Tweed Fit & Flare Mini Dress

This is the ultimate party dress for the girl who needs the perfect choice for the holidays. It's giving modern brocade and I'm 100 percent ready for it to appear in my closet. Even if I can't get my hands on it, I sincerely hope you can because you'd look stunning in it.

Just look at the fit & flare fit. It's known for being one of the most flattering designs for all body types and it happens to make us petite girls look like we're floating from one room to the next.

For anyone who knows animal print and fall belong together: 

Miss Selfridge Animal Print Dress

To you, animal print during fall is like wearing florals during spring; you have to have it. I don't blame you because it's basically a neutral print that you can build several outfits around. This dress has a little bit of leopard and cheetah print mixed together for something that feels fresher than what we've seen, meaning it could very well work in your favor.

MANGO Leopard Print Dress

But if you don't care about mixing animal prints, stick with the tried and true leopard pattern us millennials love so much. You seriously can't go wrong, considering this dress happens to get the pattern and color just right (meaning it doesn't look cartoonish). Plus, it's begging you to throw a denim or trench coat over your shoulders.

The best plus size dress for the girl who loves flared hemlines:

Lane Bryant Shimmer Shirred Dress

I'm a firm believer that petite styles aren't reserved for one body type so I couldn't wait to share this cute dress with you! It has that familiar fit & flare fit I mentioned earlier, plus there's a bit of shimmer if you need something that feels holiday-friendly.

Petite LC Lauren Conrad Swing Dress

Let's keep the party going with this all-over sequin dress from Lauren Conrad's collection at Kohl's. This simple swing dress can be paired with black tights and heels that feature a diamante moment.

PrettyLittleThing Bandeau Structured Velvet Dress

Want a petite dress that feels a little more structured? Check out this cute velvet dress! It's designed to cinch your waist while flaring out your hips to create something that doesn't feel like you're reliving that one dress you used to wear to the club.

For the girl who doesn't care about petite 'rules':

The Somerset Maxi Dress

Maxi dresses can be a hit or miss for petite girls, but this dress works exceptionally well. It'll stop right before your ankles instead of dragging the floor, giving you one of the best fall dresses you'll own. I'm biased because I think everyone should have at least one black maxi dress in their closet that's not ribbed or fitted. Though those options serve their purpose, especially on cozy days, I think flared or flowing dresses have an appeal that complements fall.

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."