How To Wear Crop Tops in Fall & Winter

Approaching autumn & winter, I have almost no concerns other than it won’t get here fast enough. I’m already ramping up my fall inspiration on Tumblr and just got my first pair of “it’s gonna be cold” boots last week.

…But I did say almost. With the rise of crop tops last year and the fact that they finally caught my interest this year, am I supposed to just hide them deep in my closet until next summer, shamed and shunned by the cold months? This is something I definitely did not think through before acquiring two that I absolutely love and want to wear allthetime. I’m not ready to stop wearing them, but I am ready to not be freezing and tummy-baring in the middle of November. The budget shopper in me is ashamed that I did not think this through.

So the only way to save face at this point is to find a way to wear them in fall & winter without spending too much money, or ideally using things I already have.

After stumbling upon the answer, it seemed obvious: wear your crop tops over a dress.

fae in gold crop top dress

Source: Fae in Gold

My favorite way to wear crop tops is with high waisted midi skirts, so why not just continue that high waist right up to the shoulders? Add crop top over the top, and you have a cute, covered, and still figure-boasting way to wear all those things you spent your money on this summer.

As long as your dress is slim at the waist, you should be able to play with just about any shape. Since my crop tops are particularly loose and thus can look a bit wide, I am on the lookout for bodycon dresses, preferably in the midi-skirt range.

boohoo bodycon midi dress

Boohoo Jen Square Neck Bodycon Dress, $15.99*

That way, the crop top can kind of sit atop an already-defined silhouette and I don’t have to worry about looking like I’m wearing Dad’s t-shirt.

Another silhouette that I’m falling in love with includes princess-like, voluminous maxi skirts and crop tops. 

street tonic crop top maxi dress


This might be a summertime carryover for those of who are are ahead of the game, but the idea that I could hide some leggings or microfiber fleece tights underneath a maxi dress or skirt makes me feel ready to get cozy.

Again, I think the only “””rule””” is to keep your waist defined, but after that it’s all fun & games. I am leaning towards a nipped-waist maxi skirt made with tons of fabric.

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mon cherries crop top maxi skirt

Source: Mon Cherries

Most recently, Olivia Palermo kind of nailed this look at her own wedding, where she wore a voluminous tulle and chiffon skirt with a cropped, fitted sweater. I don’t really follow celebrity fashion much, but I was definitely Googling for more pics once I caught a glimpse of the rear view. Her top wasn’t cropped, but it still mastered the extreme fit & flare shape perfectly. (& those shoes!!)

dorothy perkins pleated georgette maxi skirt

Dorothy Perkins Pleated Georgette Maxi Skirt, $57

Finding a high, structured waist on one of these poofy skirts seems to be a little bit harder to find than your average maxi skirt, but there are some gems here and there! I’m willing to wait for the perfect one.

I just got a new crop top in the mail from ThredUP and it has a photographic print of a goose on it!!!!!1 I am beyond excited and once I procure a perfect, basic, black midi dress, you will all see it. Many times. too many rimes.

How are you going to use your crop tops in the cold months?

  • Emily Ahlbum

    I just recently found the courage to rock a crop out and I never thought of doing it this way! Super cute and I cannot wait to try!

    • YES, awesome! Go us! :) The dress underneath also makes me feel a little bit more covered and therefore less self-conscious, so it’s a win-win.