
I am a dress girl through and through, and I hate to retire my dresses just because it gets cold outside. So I’ve been on a mission to figure out how to wear dresses in winter. I mean obviously, tights and boots are a key component, but I really hate being cold, so I need a few more tricks. I walk to the Subway in the morning (it’s not far but still, in super cold weather, it can feel brutal). And living and working in the city means I am constantly running around in the cold during the winter and doing a lot of walking to get cabs or ubers or go to events or meetings or appointments, so I need some hacks for how to wear dresses in winter that go beyond keeping your legs and toes covered, ya know?
Some tips for how to wear dresses in winter:
- Wear tights or leggings under your dresses
- Go for wool or fleece-lined tights and leggings over sheer (unless it’s a fancy event) to keep legs warm.
- Opt for longer dresses that allow you to wear leggings under and help add an extra layer of coverage.
- Wear closed toe boots. I like tall boots because they offer an extra layer and work well with both short and longer dresses and tend to be more flattering because, unlike, ankle boots, they don’t cut off your legs.
This dress is so not my style and yet I had to have it. Does that ever happen to you? I think it speaks to the boho Pisces side of my personality that occasionally comes out? Andrew calls it my Thanksgiving pilgrim dress, lol. Kinda of true. I appreciate the colors though in the doldrums of winter, and the fact that I can wear thermal leggings underneath in the dead of winter, which are so much warmer than tights. Right now, it’s just too damn cold to wear dresses and tights, so this is a good solution for days where I want to dress up a little. The nice thing about this one is I feel like it could work in springtime too with the right sandals and maybe a denim jacket, but boots and a furry scarf make it perfect for winter.






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