How to Wear Flare Ankle Jeans in the Winter

Yesterday on Substack I shared a sale round-up that included my absolute favorite pair of jeans: The Hustler Ankle Flare in the faded medium wash by Mother. They retail for $278, which I have paid full price for with no hesitation, but right now they are marked down to $139. Somehow, almost every size is still in stock.

I wear these jeans all year long. In the summer I pair them with sandals and sleeveless tops. In the spring and fall I reach for light layers and sneakers. And in the winter they work beautifully with sweaters and coats..

Since they’re a reader favorite and a personal staple, I thought I would take this opportunity to show you a few ways to wear ankle flares in the winter. I get a lot of questions about what shoes work, what outerwear pairs best, and how to make the cropped length feel intentional in colder weather.

Before we get into the outfits, one quick note. Winter looks different depending on where you live. I am on the East Coast and it is currently freezing, but we still get mild days mixed in. So use common sense. If there is a foot of snow on the ground, you are not reaching for ankle flares. But on dry, crisp days, or if you live in a year round mild climate, they are perfect. I wore mine earlier this week with a chunky sweater and boots and the proportions felt just right.

And please do not send me emails yelling about exposed ankles. We all dress for the weather we actually have. You know your climate better than I do, and I am simply giving you options. If you prefer a full-length style, last week I shared how to style a traditional bootcut jean. You can see it here.

How to Wear Flare Ankle Jeans When it’s Cold Out

As always, the items featured below include pieces I know many of you already have and love. Showing them here is my way of making sure the things you purchase through our links continue to add real value to your wardrobe. I also included a few new finds I am genuinely excited about.

Let’s start with our first look all built with the The Hustler Ankle Flare by Mother.

Ivory Layers With a Pop of Leopard

This outfit is a study in soft winter neutrals with one intentional statement. Start with your ankle-length flares as the base and add a creamy ivory sweater for warmth and texture. This one is the CashSoft Shaker-Stitch Turtleneck Sweater from Gap, a cotton blend currently on sale for $39 and available in XXS – XXL in regular, tall and petite.

If you want something a little more elevated, our friends at Quince have a gorgeous Mongolian Cashmere Funnel Neck Sweater for $120.

It is no secret that I love a good coat and have been building a small collection for years. So the idea of matching my coat to the rest of my outfit truly delights me. When the coat feels like part of the outfit instead of something you throw on at the last second, the whole look comes together with so much more intention.

Featured here is the Chevron Pattern Drape Collar Wrap Trench by Sam Edelman. The chevron detail is woven into the fabric, which gives the coat a subtle, elegant texture that instantly lifts the entire look. It adds interest without overwhelming the outfit and makes the monochromatic palette feel thoughtful and elevated.

Then we finish with a few accessories I am genuinely excited about. I just received the Odela Heels Leopard Calf Hair slingbacks from Dolce Vita. They were originally $160 but are currently on sale for $99 and still have a full size range. I love a slingback with an ankle jean, especially when there is a slight flare. The shape of the shoe complements the cropped length and gives the outfit a polished finish. These are a true closet staple.

For the bag, I am highlighting the Tory Burch Perry Mini Grain Leather Tote Bag, which I also featured in yesterday’s Substack sale round up. It is a small crossbody with a structured shape in the perfect cognac shade. It gives the outfit a little contrast and keeps everything grounded. It is currently 30% off at Neiman Marcus.

To finish the look, I added the Et Tois Studs from Electric Picks. They pair a pear-cut crystal with a sleek baguette, creating a subtle bit of shine that works beautifully with the soft layers and textures in the outfit. I love the size of these, they stand out without being overwhelming.

Casual Layers for a Cold Day

This outfit is built around simple pieces most of us already have on hand. Start with your ankle flares and layer a classic white tee under a black sweater.

For the tee, you want something with a high enough neckline that it peeks out from the sweater. You have lots of options here. Featured is the J.Crew Vintage Jersey Classic-Fit Crewneck T-Shirt, on sale for $16.50 with sizes up to a 3X. I also mentioned The Perfect Tee by Nuuds last week, which is another great staple at $52. Again, just giving you options.

Over the tee I added the Cotton-Blend Relaxed Crewneck Sweater from Gap in black. It is oversized enough to give you a casual look and sits comfortably over a tee without being too big. It is on sale for $63 and comes in sizes XXS–XXL in regular, tall, and petite. But any loose-fit sweater will work here.

I added a soft gray scarf for warmth and texture, and I love how the lighter tone breaks up the darker top half. Featured is the Shadow Gray Cashmere Blanket Scarf from Tuckernuck. It is bigger than it looks in the image, and you can actually wrap yourself up in it. It is on the pricey side at $198. You can find versions of this anywhere, and Quince has a Mongolian Cashmere Scarf that is more traditional and under $60.

For accessories, I chose my go-to Boat and Tote from L.L.Bean and a pair of clean white sneakers with black laces from Keds. These were a reader favorite last month, so this is a great way to style them. The tote adds utility without weighing down the look, and the sneakers keep everything easy and comfortable for a day of errands or casual plans. A gold chain from BaubleBar ($48 but you get 20% off at check out) adds a bit of shine and pulls the whole outfit together.

Go ahead and throw on your puffer. Last month everyone loved the Squall Waterproof Insulated 3-in-1 Winter Parka from Lands Ends, which is quickly selling out.

Rich Browns for a Warm Winter Look

This outfit leans into deep, chocolatey browns that feel warm and luxe for winter. Start with your ankle flares and add a textured sweater in a rich espresso shade. This one is the Fireside Sweater in Merino-Cotton from Banana Republic. It retails for $120 but is currently 40% off, and available in XXS–XXL. The color adds depth without overwhelming the jeans and creates an easy base for layering.(Available in several other pretty colors all more reasonably priced when marked down.)

For outerwear, I chose the Manteco Wool Coat with Belt from Mango. This is a wool coat that retails for $299, and you can use code HOLIDAY30 for 30% off, including plus sizes. The contrast between the lighter brown coat and the darker sweater gives the outfit dimension and keeps everything from blending together. The sweater color also matches the buttons on the coat, which makes the whole look feel cohesive.

To keep the palette cohesive, I added suede ankle boots in a matching brown. The higher shaft works well with the cropped flare, closing the gap at the ankle on colder days and giving you a clean line. These are the Jane High Heel Pull-On Sock Boots from The Drop on Amazon. I have them in black and brown and they are fantastic. I reach for them a lot at this time of year and have owned them for two years now.

For the bag, I am excited to try a new-to-me brand called The Horse. This style is the Friday Bag. The Horse creates bags that lean heavily into 90s simplicity. They are clean, unfussy, made with Italian leather, and offered at great price points. This one is $199. It plays off the browns without being too matchy and brings in a subtle hint of color that still feels neutral. Finally, one of the best selling earrings of the year from Monica Vinader rounds out the look. These are a splurge but if you are looking for something unique yet wearable and well made they are worth it.

If you like staying on top of the best sales, I keep all of my quick round ups and limited-time finds over on Substack. It is the easiest place for me to share fast-moving deals in a simple, easy-to-scan format. Prices change and inventory moves quickly, so that is where you will always find the most up-to-date information.