How To Wear Your Crop Tops In The Fall

As basic as it sounds, I must admit: I love a good crop top. And, unlike many of my more weather-obliging friends, I find a way to sneak a few crop tops into my ensembles every season. Seriously, I can (& have) venture outside during the dead of winter in some of my favorite crop top outfits. Because in this world, there are two things that never break down to the cold temps: penguins, and… fashionistas, duh.


Okay, there are a lot of things that won’t break down to colder temperatures, but how many of them can slay all day while bearing their midriffs in a teeny top?

A Quick Look at the History of Crop Tops


I’m not going to lie, these tops are originally crafted for warmer temps. While these tops are more of a modern trend in Western culture, they actually originated hundreds of years ago in the Far East. The scorching weather called for less clothes and more skin, which is why women would wear saris with short tops underneath. These tops were called “cholis,” and to this day women within the Far East area still wear this traditional clothing.


Although the concept of bare bellies was introduced to Western culture at the 1893 World’s Fair in Chicago via Indian belly dancers, it was not an embraced look until the 1940‘s. This era is one of the most impactful decades in fashion, introducing a whole whirlwind of styles and ideas we still wear today — including the Westernized crop top. Women began to embrace the idea of showing off some more skin, but there were definitely some more conservative mindsets who disagreed. For example, in 1945 a woman in Central Park was fined $2 for wearing a halter crop top.


But as the decades went on, society’s appreciation for the tiny top grew larger. By the 1980’s, a crop top was considered an essential for every woman’s closet, and even some men were rocking the cropped shirt style. And now, it’s one of the most popular pieces for women, and is available in a variety of styles.

The Modern Crop Top


While many reserve this short shirt for the warmer months, I follow the cropped path year-round. From the signature short sleeved top to more seasonal stylings like cold shoulders and long sleeves, there are endless ways to add this chic piece to your daily fall ensembles. It’s a cute, flirty way to spice up your outfits for the season, so why not rock one of these in the brisk weather?


Of course, there comes the concern of feeling chilly, but fun layers are key to staying warm in the colder months. Leather jackets, knit scarves, and cozy cardigans are just a few of the hundreds of outerwear picks at your disposal.


But, I know creating an editorial-ready outfit is much easier said than done, so let me do the work for you. These are some of the best crop top outfits that I’ll be donning all fall (and winter!) long — and you should be wearing them, too.


In a styling crisis? Been there, done that. Try out some of these cute crop top outfits to refresh your fall styling game.


The Easy Route: A Long Sleeve Crop TopHow To Wear Your Crop Tops In The Fall 2

A simple way to style a crop top for the winter season is to grab a long sleeved top, and let it do the rest of the work. This mustard yellow hue is perfect for fitting into the autumn aesthetic, and I adore this top when it’s paired with fitted black pants.


Pleat Crop Top



Compression Slim Leg Pants, Size 10 - Black



Lauren Studded Ballet Flat, Size 10.5US / 40.5EU - White



Queen Margaret Embellished Ostrich Shoulder Bag - Ivory


The Classic: A Black Crop Top

How To Wear Your Crop Tops In The Fall 3

A posh black crop top is fitting for any season. And it’s pretty easy to style, too: simply wear your favorite vibrant cardigan and high waisted denim to create the perfect fall ensemble. Pair your look with some classic black heels to give this casual look a major upgrade.


Macie Crop Top

$98 $45


High Rise Ankle Crop jeans



Cashmere cardigan



Bb Pump


The Lazy Day: The Crop Sweatshirt

How To Wear Your Crop Tops In The Fall 5

For those casual lazy days, a cropped sweatshirt is a must-have. It’s great for those times when comfort triumphs all, but you still want to have just a bit of polished style added to your look. For a cool contemporary look, pair this sweatshirt with a cool leather skirt, sneakers, and some fun earrings.


Logo Cotton-Blend Crop Hoodie



Button Front Leather Skirt, Size 4 US / 36 FR - Black



Triple S Logo-embroidered Leather, Nubuck And Mesh Sneakers - White



Link Earrings


Staying on Aesthetic: The Cropped Flannel

How To Wear Your Crop Tops In The Fall 6

If you’re looking for the perfect crop top to go pumpkin picking in while you sip on your venti PSL, then this is your answer. Embrace the fall aesthetic in it’s fullness with this top, and pair it with some distressed jeans, UGG boots, and a cool crossbody bag to create the ultimate autumn look.


Plaid Flannel Crop Hoodie




$99 $33


Bailey Tall Boot with Bow, Kid Sizes 13T-4Y



Ghianda Braided Chain Shoulder Bag


The Cold Shoulder: Off The Shoulder Crop Top

How To Wear Your Crop Tops In The Fall 7

Cold shoulder tops are a classic for the fall season, so don’t be afraid to go a little cropped in your style with this autumn essential. Pairing them with some fun wide leg pants, open-toed heels, and an eye-catching necklace will do just the trick for creating a flawless fall look.


Off-The-Shoulder Rib-Knit Crop Top

$158 $68


Lora Wide Leg Utility Pants

$375 $251.25


Alicia Block Heel Sandal, Size 6 M - Black




$119 $66

The Professional: Cropped Blouse

How To Wear Your Crop Tops In The Fall 8

Some people say there’s a time and a place for a crop top, and I say that anytime is fitting for a crop top. This cropped blouse from Helmut Lang is physical proof that you can easily turn this usually NSFW style into an office-appropriate look.The slightly longer cropped cut allows you to still stay concealed, but has a slightly edgier attitude that will spice things up at your cubicle. 


Cotton Crop Shirt

$295 $104.97


Straight Tapered Slouchy Pants

$258 $129


Dylan Square Toe Pump, Size 9.5 M - Black



Cabata Calfskin Leather Tote - Black


The Casual Look: Graphic Crop Top

How To Wear Your Crop Tops In The Fall 9

A fun graphic top is all you need this fall season to kick your style into high gear. It can be as simple as this cherry top, or you can wear one of your favorite cropped band tees for a grungier look. Pair them with a cozy pair of leggings, a cool backpack, and some fun jewelry to create a laid-back autumn look. Bonus points if you top it all off with chic outerwear like a leather or denim jacket.


Cherry Pop Crop Top

$98 $68.6


Drive Legging



Adidas Original National Backpack - Red




$369 $276

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