How to Style Summer Dresses in Winter

Hi, friends! Welcome back to Stylishly Good Vibes! Wow—what a chaotic few months it has been since my last blog post! I’ll fill you all in about what I’ve been up to when the pieces all fall into place! Either way, just know that I’ll hopefully have more time for the blog!

Today’s post is all about how to style those summer dresses that have been hanging in your closet for the past six months. I don’t know about you, but my wardrobe doesn’t change much from summer to winter. What do I mean by that? I don’t remove anything from my closet as the seasons change—simply because I know I can make just about any piece work whether it’s July or November!

Make Winter Styling More Fun

During the winter months, I quickly tire of wearing pants every day, so styling some of my favorite skirts and dresses is a great way for me to feel inspired. Living in the Midwest definitely has its style quandaries—especially since you don’t know if it is going to be sunny and 60 one day, then a blizzard the next. But regardless, every piece in my wardrobe always gets its time to shine throughout the year!

The Perfect Slip Dress

The slip dress I’m wearing in today’s post is from Caite & Kyla. Their slip dresses are absolute perfection. I always love the graphic patterns they use plus they’re super lightweight and easy to style.

Pattern Play

If you’ve been following along for a while, you know how much I love a pattern play. So when I wanted to style this slip dress for a 30-degree day we had last week, I knew I wanted to pair it with some kind of sweater. Although this sweater doesn’t match perfectly with the dress, it still works. That’s the thing about playing with patterns: you can’t think about it too much. The second you start to overanalyze if something “works,” that’s when you psyche yourself out from wearing it in the first place.

If your eyes gravitate toward a pattern play, just go for it!

This balloon sleeve sweater from Urban Outfitters is always on repeat during the winter months. Pro tip: if you’re in need of high-quality sweaters that won’t break the bank, check out Urban. I have so many sweaters that I bought from there that have truly stood the test of time. The key is to never put them in the dryer. Air dry, always!

Accessorize with Me

As far as accessorizing this look, I opted for this cropped mauve jacket from Free People and a pair of my Dr. Marten Leona boots. Could I have added a belt to this look? Sure! I’m just not the biggest fan of belting dresses. I don’t know why, it’s just one of those things I can’t get behind for my own personal style. Plus—I like when things fit looser, so having the layered look styled this way works for me.

Looking to winterize your summer dresses but not sure where to start? Here are my tips!

  • Style it like I did, throwing a cropped sweater on top.
  • Add a long-sleeve turtleneck underneath the dress.
  • Try a graphic tee underneath and a denim jacket on top.

Well, that’s all I’ve got for you today! I hope that you all have a great few weeks and I’ll be back on the blog soon to share more! 🙂

Until next time!


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