The Hottest Cold-Weather Outfit Ideas to Wear With Flats

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!

Taylor looks totally adorable, posing in her opening set body suit while sitting on a black chair in the cleaning cart. While understanding how the "August" singer got around in the cart would have been enough for me, there's plenty more inside to unpack, too. Here's everything I noticed in the cart:

• A floral cat illustration: Such classic cat-lover behavior.
• Printed out "Animals of the Day" flyer featuring Olivia, Meredith, and Benjamin: She's such a proud cat mom!
• A painting of a waterside town: Fans pointed out all over social media that this is potentially Cardiff, one of her many stops on the tour.
• More hanging and taped-up decor: I'm dying to know what else Taylor wants to see before she hits the stage!
• A little gold and red trinket on a ledge: Is Taylor a trinket girl?!
• A little fan in the corner: And thank goodness, because you know that girl puts in hard work on that stage!