If you’re looking for a balance of casual and comfortable, this post is for you. I’m styling a few different outfits for winter with jeans and sneakers. All of the outfits are layered and warm and will keep your ankles covered. To show a little bit of variety I styled straight, flare and cropped flare jeans with sneakers.
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Winter Outfits with Sneakers
My Sizing: I’m 4’10”, and my bust, waist, and hip measurements are 32″, 24″, and 36″. My inseam is 25″ (the measurement from the inside of my leg to my ankle bone). The clothes shown are unaltered and show how they fit me right from the store. I list my sizing beside each item to help you compare when shopping online. When referencing my true size, that is often the smallest option available at a brand or petite xxs/00/24. I wear a size 5 shoe.
With Flare Jeans
Flare jeans are a great option with sneakers. They’re the only style that adds a good amount of balance – so much so that you can wear these with a slim sneaker like I did here as well as chunkier athletic sneakers. The jeans I’m wearing here are the ’96 Flare Jeans from J.Crew. They also come in a few other washes and styles. This medium wash has pockets on the front and slash pockets on the back. I have them in two different washes and found them both to run large, so I went down a size to 23 petite. The website notes these jeans as having a 29-30″ inseam, but I found mine to have a 28-29″ inseam in petite. This length works well for me with sneakers and a low 2″ heel. To note, I have also noticed that these jeans stretch out with wear and shrink some in the wash (so skip drying if you don’t want them to shrink).
In both outfits I went with the same outfit combination: jeans, sweater, and a long coat.
Jeans Petite 23 sized down | Similar Sweater XXS | Similar Coat Petite 00 (same fit, my coat is from last year, same brand) | Socks | Sneakers | Scarf | Bag | Layering T-Shirt XS | Earrings
Coat Petite XXS | Jeans Petite 23 sized down | Sweater XS signature cashmere in rich burgundy | Scarf | Socks | Layering T-Shirt XS | Sneakers | Bag | Earrings
Straight Jeans
To stay warm in the winter, I like to pair high top sneakers with straight jeans. As it warms up, they look great with a little bit of ankle showing and pair well with slim and chunky sneakers. But, for my winter look I tuck the sneakers under the jeans and I pair them will tall, warm socks. I wore this exact outfit at Disney last week (it was cold at night). It’s simple and comfortable – sometimes the only thing you need to make an outfit look pulled together is a great fit and a nice mix of colors. The coat and the jeans are both from Quince. I’m wearing the coat in XS and it fits me well overall. If you’d like to see a full review of the jeans, check out this post.
Layering T-Shirt XS | Coat XS | Jeans 24 x 26″ | Sweatshirt Petite XS | Bag | Socks | Earrings | Sneakers
Cropped Flare Jeans
I wear cropped flare jeans with sneakers, the same way I wear straight jeans with sneakers. In the winter I go for a high top style I can tuck under the jeans so I choose a pair of jeans that comes close to the top of my foot. In the spring and summer, I often choose a pair that is a little bit shorter, more like ankle length. These jeans are stretchy and comfortable and also pair well with chelsea boots. They do, however, have a very high-rise (they come above my belly button), so they’re not a pair that my short torso friends will appreciate.
Sweater XXS | Coat Petite 00 | Jeans Petite 00 | Layering T-Shirt XS | Socks | Sneakers | Bag | Scarf | Earrings
After my series of workwear through January I have been getting a lot more requests for casual outfits. So, no worries, casual is just around the corner. I’ll be shifting my focus to preparing for spring and transitional weather in upcoming posts. So if there is something you’re hoping to see be sure to send me a message via email or IG DM!
-Brooke
