How to Style a Crop Top for Any Occasion

Female wearing a red crop top with sunglasses is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to As an Amazon Associate we earn from qualifying purchases. See our disclosure here.

Last Updated on June 30, 2021

Think back to the quintessential red carpet clothing of the 90s…are you seeing visions of wonderfully-taught tummies peeping out beneath crop tops?

Perhaps you’re seeing Britney Spears, Drew Barrymore or Destiny’s Child in all-out denim, matching leather, or defiantly-casual cropped sweaters?

What a time to be alive. 

You can guess where I’m going with this…the crop top is back in a big way! However, the fashion “rules” have somewhat changed since the heyday, so here’s our take on how to style a crop top in the 21st century.

No matter your size, shape, age, or profession, there is a modern crop top look out there for you. 

High-Waisted, Wide-Leg Pants…30’s meets 90s 

High-waisted, wide-leg trousers are timeless and flattering on almost all body types, making women into badass fashion icons since the 1930s. A crop top with high-waisted pants is an iconic look, as it shows a small sliver of bare skin while maintaining the edge and bravery of the crop. 

What’s more, by seeing the entire trouser from high waistband to hem, the legs are given the appearance of being long and model-worthy. An off-the-shoulder, long-sleeved crop top in a fitted, stretchy fabric is a complete win, giving extra privacy and warmth in winter months. 

This is a fabulous option for people who are a little apprehensive about trying crop top looks as it gives extra coverage to the tummy. Make it double vintage by pairing with a pair of T-bar heels, a beret, and pearl earrings. The perfect way to return to old-Hollywood glamour while embracing our beloved 90s trends. 

Overalls With a Peep of Skin 

Let’s get super 90s and embrace the overall, preferably with low-cut sides. Wear a cropped tee underneath, so the curve of the waist peeps through.

For anyone out there who doesn’t quite have the same torso as they did in the 90s (I hear ya, girl!), overalls provide comfy coverage while showing off the best part of your midsection. In saying that, if you want to wear a mesh knit halter crop and low-cut jeans, you go for it! 

A-Line Mini and Leggings 

Time to channel Baby Spice, the queen of cute! An A-line mini, preferably mid or high waisted with a cropped tee or fitted sweatshirt looks feminine and flirty while giving enough coverage to feel comfortable at work (or generally as a 30-something adult). 

The mini skirt brings a wickedly retro 1960s vibe to the 90s crop, (we love to clash decades!). Play around with color and texture to suit your design preferences.

Style tip
Picture a black velvet mini with a pink or purple cropped tee or sweater, and black leggings (for Winter). Throw on worn-in ankle boots, or Docs for classic grunge, or kitten heels for a sweet moment during the Summer party season.

Read: Grunge Fashion Accessories That Will Turn Heads

Cargo Pants and Sneakers 

Since we love to hark back around here, let’s hark back to the good old days of the super-baggy cargo pants. Go for the classic Khaki green, baggy cargo pant sitting mid-rise just above the hip, and pair with a fresh white cropped tee and sneakers. 

For a modern take, keep the sneakers sleek and streamlined as opposed to chunky. This is an excellent travel outfit as it’s cozy, non-restrictive, and walk-friendly. 

Bodycon skirt with an oversized denim jacket 

If you’re feeling game, one-up your crop top with a body-con skirt to show off your stellar hips. Picture a floral bodycon skirt with a fitted cropped sweater in a contrasting tone, with gold-accented accessories and slicked, J-Lo-worthy hair. 

You could even opt for a matching skirt and top set (an excuse to hit the shop for a new outfit? You’re welcome!).

Contrast the super-tight style with an oversized blue denim jacket, or even a subtle-striped tailored blazer for more streamlined style preferences. Time to post a bunch of social media photos cause you’re a living work of 90s-themed art. 

Office-friendly crop top looks

I’m sure you’ll agree that an all-out, navel-baring crop top look isn’t exactly accepted in most office environments, even today. However, there’s absolutely a place for it! It’s all about how much skin is on show, and what’s happening around said skin. 

Style tip
Imagine a pantsuit with high-waisted pants and a long-line blazer left unfastened and open, in navy or black. Under the blazer is an ivory or white cropped tee or tank, revealing only a couple of inches of skin between navel and ribs. The blazer tapers the exposure for extra coverage and professionalism. Who could complain? And if they do…remind them “ahem, it’s the 2020s, my midriff isn’t harming you, sir”.