Styling Your Dresses and Skirts Through the Cold Months

fall dresses

When your week consisted of 2 wine dates with girlfriends and my first Blues vs. Blackhawks game, I pretty much can’t complain about the week being long. This week was basically one big weekend for me. Oh minus that whole 9-5 job I go to during the day. We’ll just say that doesn’t count.

But holy cow, it’s already Friday and better yet it’s already only a few weeks away from Thanksgiving and with Thanksgiving comes my favorite season: skirts/dresses with tights and boots season. 

Now depending on where you live, there’s a good chance you may already be feeling the cool weather effects of fall. Well unless you live in Chicago and are still living it up like it’s summer! But during a normal November the leaves are changing, the air is crisp, and now you have the perfect excuse to start layering your outfits for some really cute clothing combinations. Your first instinct may be to pack up your dresses because it will be far too cold to continue wearing them, but before you relegate those flowing frocks to the back of your closet, check out a few helpful tips on how to wear your dresses and skirts from now until winter is over.

Floral dress

If you’re looking for a look with a little more edge this fall, throw on a pair of boots, a cardigan, and a sweater over top a floral dress. Create a similar look with a skater skirt and a cable knit sweater, and if in need a little extra warmth add a pair of cute knit socks. While I’m not usually a combat boot girl, but I found a pair I’m in love with the other day and they are definitely on-trend. Plus they can quickly make an ultra-feminine outfit appear a little more grown up, not to mention the much needed contrast and substance a pair of chunky boots would provide during cooler weather. For some under layering dress options, check out the latest post on autumn dresses from Vogue.

closed toe pumps

Closed toe pumps are a great way to add a touch of feminine sophistication to a work-appropriate outfit. Wear these with a sweet and simple high waisted A-line skirt, a long sleeve gingham button down and a pair of opaque tights. When it’s extra chilly out, layer on a double breasted coat and be sure to button up! Another pretty way to glam up a dress or a skirt for the office or a date night is to pick up a few different pairs of pretty textured tights. I may own way too many pairs of these. The options are endless, you can choose from lace, polka dot, hounds tooth, stripes, and everything in between, plus they’ll keep your legs toasty all winter long. Need some inspiration for some great fall dresses? Then check out this page on Lyst.

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Think you can’t wear lace during fall and winter? I thought not too, until I saw this article by Marie Claire and although my lace dresses are quite that elaborate, I’m still determined to mix things up this season and incorporate this frilly fabric. Wear a lace dress with a blazer or leather jacket, black tights and black booties. Or, opt for a sweater dress paired with lace socks that peek out of knee-high boots. You can also add a long sleeve tee under the dress for added warmth on your arms.

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Don’t pack up those dresses and skirts just yet! Now that you’ve gotten the scoop on how to wear these items through the fall and winter months, it should help take the guesswork out of putting together some great looking outfits this season. 

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Any favorite skirt/dress looks you’ve been admiring this season? Maybe a funky pair of tights you’ve had on repeat? Share your go-tos this fall below!

5 thoughts on “Styling Your Dresses and Skirts Through the Cold Months

  1. DANAE GARCIA

    Such great tips! I love styling dresses and skirts with ankle boots, I feel they look so chic and comfy!

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