8 Ways to Wear Your Fall Boots With Spring Dresses

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.

As a gal with a little more meat and muscle on her bones, this has always been a problem for me. It’s infuriating, but it feels even more isolating. I can’t always wear the same styles that smaller women do, and even if I do find similar boot designs fashioned for wide calves, they look noticeably cheap or simply don’t check all the boxes in terms of my desired look.

I grew tired of saving all the “perfect” tall boot outfit inspo pics to my Pinterest board only to find that the boots in question had way too small of calf sizes, so I did what I always do when I shop for size-specific pieces: I took to Reddit.

I primarily consulted r/femalefashionadvice, r/plussize, and r/ausfemalefashion to see what people like me are saying about wide calf boots. The frustrations with finding good-looking, comfy tall boots was pretty similar across all three subreddits. As one passionate user put it:

“Even at a size 6, I have never been able to just buy any old pair of boots and have them fit. It is interesting to me how we've made great progress the past several years in regards to body inclusivity, yet somehow there seems to be a huge lack of sizing in regards to tall boots… It makes me so sad to see these beautiful boots everyone else gets to wear, slouchy, over the knee, western inspired, leopard/snake print, etc. Nothing like that comes in wide calf.”

Luckily, Redditors across all three threads suggested a handful of brands that actually offer cute wide calf boots with extended sizing. I had never heard of a few of them, but after scrolling through their sites, it felt like I struck gold.

The top-recommended brands for wide calf boots:

• Penningtons
• Børn
• DuoBoots
• Franco Sarto
• Sam Edelman
• Billini

Franco Sarto Bowman Wide Calf Knee High Boots

You're meaning to tell me these chic boots can really accomodate my calves?! The deep red color already had me sold, but that 15.75-inch calf circumference made this style so much better. They also come in a smooth brown color and a foxy faux-snake pattern, if those speak to your personal style more.

Børn Hayden Extended Calf Boots

The suede leather construction of these boots honestly rivals that of the beloved Campus boot, but their fit is much more roomy, boasting a 16.5-inch calf circumference. These zippered boots also have a playful lace-up detail on the back that's utterly unique.

Penningtons Extra Wide Width Black Tall Heeled Boots with Harness Straps

The calf circumference on these bad boys starts at around 17 inches for shoe size 6, and tops out around 19 inches for shoe size 12. I can't get enough of these moto-style boots and I love that they have the signature harness with silver hardware around the base that other similar boots do.

DuoBoots Saffron Knee High Boots

The fact that you can choose the calf sizing yourself when purchasing these Western-esque boots is ahh-mazing. The options start at 13 inches and go up to 20 inches to hold your beautiful legs without any fuss.

Billini Granger Extended Curve Boots

From all the wide calf boot brands suggested on the Reddit threads I scrolled through, Billini has to be my favorite. They state that these adorable camel-colored boots can fit calf sizes from about 18.11 to 21.42 inches, and while they do have an elastic panel on the sides to stretch even further, I think it's discreet enough that it doesn't distract from the overall look. Score!

Baretraps Thalia Wide Calf Boots

A very similar style to my wishlist Sam Edelman boots, this black pair actually has a 16.5-inch calf circumference that'll fit my legs to a tee. The block heel is the perfect shape and height, plus the toe isn't overly pointed (I don't necessarily care for pointy toes).

Sam Edelman James Wide Calf Western Boots

Finding cowboy boots with wide calves can be a big challenge – but no more! These reddish-brown boots have a 16-inch calf circumference so you can confidently rock any and all Western looks.

Billini Oshea Curve Boots

Immediately yes. These broader-fit boots are everything you need to make a statement with your shoes. They're definitely going on my wishlist! The calf circumferences for this style start at 16 inches and go up to 19 inches based on your shoe size.

Vince Camuto Seshon Extra Wide Calf Boots

With a 18-inch calf circumference, you won't have to worry about squeezing into these tall boots. I adore the timeless squared toe and wide block heel on these!

Christmas Charades

Play charades with a holiday twist! Write down Christmas-themed clues (e.g., decorating a tree, Rudolph, Mariah Carey, building a snowman...) and have teams act them out. Keep it simple for kids, especially ones learning to read, or add some pop culture references (Buddy the Elf, anyone?) for adults-only parties.

Name That Carol!

Play short snippets of Christmas songs and have guests guess the title. To up the challenge, use instrumental versions or hum the tune. For kids, you can turn this into musical chairs with holiday music!

Christmas Trivia

Create trivia questions about Christmas movies, traditions, and songs. Bonus points for the most obscure facts! Here's a few to start:

• Which country started the tradition of putting up a Christmas tree? (Answer: Germany)
• In the song Twelve Days of Christmas, what is given on the 7th day? (Answer: Swans a-swimming)
• Which country celebrates “Feliz Navidad”? (Answer: Spain or Latin American countries)

Guess the Holiday Scent

Use candles, essential oils, or holiday-themed spices like cinnamon, peppermint, or pine. Blindfold guests and have them guess the scent. Throw in some unexpected surprises like egg nog, maple syrup or Scotch tape.

Snowball NBA

If you're lucky enough to have a White Christmas, set up buckets outside labeled with different point values. Guests toss real snowballs, or “snowballs” like white cotton balls or small foam balls if you're playing indoors, into the buckets for points.

The Awkward Gift Wrap Race

Find awkwardly shaped items around the house, like a basketball or stuffed animal, and provide rolls of wrapping paper. The fastest (and neatest) gift wrapper wins!

Ornament Relay

Hand out spoons or chopsticks and teams have to race to get ornaments from one side of the room to another.

Candy Cane Hunt

Similar to an Easter egg hunt, hide candy canes around the house or yard and let guests hunt for them. Wrap a few with dollar bills to up the ante .;)

Holiday "Who Am I?"

Stick Christmas-themed names or characters (e.g., the Grinch, Jude Law, Holiday Armadillo, Charlie Brown) on players' foreheads. Guests ask yes/no questions to guess who they are. It's a great ice breaker for new friends!

Gingerbread Decoration Contest

Anything with a ticking clock adds a certain element of hilarity to it. Give your teams gingerbread houses with icing and decorations. Let the creativity flow, and award prizes for categories like “most festive” or “funniest" or "worst construction."

Here are more Christmas games to play this season:

Jingle Bell Toss: Set up your college-era Solo cups into a bowling pin formation at opposite ends of the table. Each players tries to get large jingle bellsinto the opposite side’s cups. The first player to get a bell in each cup wins.

Human Hungry Hungry Hippo: Pair up, stand in a circle, and hand out plastic candy canes. Toss shatterproof Christmas balls in the middle of the circle. One person stands, holding the feet of the other person on the floor. The person on the floor tries to collect more balls with the candy cane than the other teams for a human version of Hungry Hungry Hippo!

Christmas Pictionary: Like charades, but on paper. Use pop culture references like "Hallmark Holiday Movie" or holiday-themed phrases like "Silent Night" for teammates to guess.

Left-Right Christmas Story Game: Make up a holiday story that includes the words "left" and "right" often. Guests pass a wrapped gift or object left or right as the words are mentioned, and whoever holds it at the end keeps the gift!

Christmas Bingo: Downloadbingo cards with holiday symbols or themes. Mark them off as they’re called out. First to yell “Bingo!” wins.

Reindeer Ring Toss: Use inflatable reindeer antler hats (or make your own) and toss rings to see who can "decorate" the reindeer.

Christmas Cookie Taste Test: Bake or buy a variety of holiday cookies. Blindfold guests and see who can identify the most flavors correctly.

Christmas Movie Emoji Quiz: Create a string of emojis that represent Christmas movies and have guests guess the titles.

Snowman Building Contest: If there’s snow, go outdoors for a snowman-building competition! If indoors, use toilet paper to “wrap” someone as a snowman.

Holiday Scavenger Hunt: Make a list of Christmas-related items like a red ornament, mistletoe, or a stocking and have guests search for them in teams.

Christmas Karaoke: Set up a karaoke machine or app and sing along to holiday classics. Bonus points for best singer or most dramatic performance!