Jessica Crum

A Lifestyle and Fashion Blog

Fashion, Winter ·

How to Wear a Dress in the Winter












Dress: Forever 21 here (similar here) // Duster: Shein here // Boots: Steve Madden here // Earrings: Red Dress sold out (similar here) // Purse: Sole Society here

Is it just me or are you guys ready for warmer weather? As much as I love bundling up in sweaters, sometimes you just want to pull out the dresses. But unfortunately, we still have a little while before it warms up, so today I’m showing you guys how to style a dress in the winter!

Start with a wintery dress. Whether that be one with long sleeves or just follows a winter color-scheme. I tend to stick to more plain colors in the winter. Meaning, I’m not going to choose a neon, flowery dress in January (leave that for spring or summer). I wear a lot more black, grey, navy, maroon and even neutrals like cream and white. I opted for a tight dress here, but you can also choose a flowy, sweater dress like this. The key is to choose a dress that isn’t too long. You want to make sure you can see some leg in between the dress and the top of the boots to create the look of longer legs. I’ll link a few more of my favorite dresses to pair with over-the-knee boots in the widget below:

Next, grab a cute sweater or duster to throw over it to add some warmth. I went a little more dressy in this look with this one, (which you could easily pair with jeans as well), but you can always go the more relaxed look with a sweater. Linking a few of my favorite dusters and sweaters here:

Finally, throw on your over-the-knee boots. If you haven’t invested in a pair yet, the time is now! They are so flattering and make your legs look so much longer. Make sure to find some that are tight around your thighs so they don’t continue to fall off. If you have small thighs, I wouldn’t really recommend the ones I have on. As you can see, they start to fall down no matter how tight you tie them. I’ve gotten a few pairs since then which I LOVE, and linking them (along with other favorites) below:


I just got these and I can’t wait for them to come in! You guys all raved about how much they’re worth the investment.

Did you guys have a good week?! I’m sad the weekend is coming to an end, but excited to get a lot done this week. It’s time to stop making excuses, and make stuff happen!



Photography by Kate Elizabeth Photography

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