How to Style Cropped Bootcut Jeans: Fashion Tips

Because skinny jeans aren’t the only jeans out there.

This post may contain affiliate links, which means we may receive a commission if you purchase through our links. Please read our full disclosure here.

Madewell cropped bootcut jeans with frayed hem - how to style cropped bootcut jeans

Welcome to the latest edition of Ask CF! Every two weeks, we select a reader fashion question and answer it here on the site. Do you have a specific fashion question for us? Scroll to the bottom of this post to learn how to send it our way!

Ask CF Question

Dear CF,
I’m a bit bottom heavy and find flared or bootcut jeans to be the most flattering. But among all these skinny jeans I’m at a loss to transform these into an outfit that doesn’t scream hippie or frumpy. Help!
Thanks :)-Lost in the Flare

Our Response

Dear Lost in the Flare,

While bootcut and flared jeans may have been viewed as unstylish in the past, this season, fashion’s most influential trendsetters are wearing every style of jeans but skinnies. That’s not to say that there’s anything wrong with them–it’s just that people have been branching out more and seeing, as you have, that skinny jeans aren’t the only option out there.

Having said that, although bootcut and flared jeans might be a little bit harder to find at “trendier” shops these days, there are still a myriad of ways to style them that won’t make you look dumpy or like you just stepped out of the ’70s.

{Related Post: The Cutest Flared Jeans Outfits We’re Wearing Right Now}

So, keep on scrolling to see the outfits that I have put together for you.

Outfit #1 – Isola Cropped Bootcut Jeans & a Crop Top

Isola Cropped Bootcut Jeans & a Crop Top - how to style cropped bootcut jeans

Product List

The Isola cropped bootcut jeans from Citizens of Humanity feature a flattering mid-rise with a close fit through the leg and subtle bootcut flare. This cropped fit hits right above the ankle, making them a versatile bottom paired with heels or boots.

The Tawny ruffled broderie-anglaise crop top from Alice+Olivia features a smocked panel, square neck, short sleeves, and cropped length. The ruffled detailing and broderie anglaise fabric give it a feminine, romantic style.

Also Read: How to Wear a Crop Top (+ 4 On-Trend Outfits You’ll Love)

Outfit #2 – Chic Jeans, Luxurious Blazer & Classic Striped Tee

Chic Jeans, Luxurious Blazer & Classic Striped Tee - how to style cropped bootcut jeans

Product List

The medium blue cotton bootcut cropped jeans from Tu es mon Tresor feature classic five pockets, a concealed front fastening, belt loops, and a cropped bootcut leg.

This light yellow blazer from Nanushka is a tailoring classic with single-breasted fastening and tortoiseshell-effect buttons. It exhibits the brand’s vision of pared-back glamour through a clean design and luxurious fabric.

Modeled after traditional Breton styles, this Jil Sander T-shirt is crafted from ribbed cotton jersey and decorated with classic stripes. It is punctuated by the label’s signature patch at the nape, making it a wardrobe staple.

Also Read: Easy Outfit Formulas: Striped Top + Floral Skirt

Outfit #3 Preppy Twist

Preppy Twist - how to style cropped bootcut jeans

Product List

This denim-on-denim outfit forms a great combination for a casual yet polished daytime look. J.Crew’s 9″ demi-boot crop jeans in Brommell wash pair perfectly with their Louisa lady jacket in denim for a coordinated ensemble.

The vintage rib shelf-bra tank top provides a comfortable layer underneath the jacket. To complete the outfit, the Winona penny loafers in spazzolato leather add a preppy touch. 

The pearl ball necklace brings just the right amount of feminine flair to finish off the look. With sustainably sourced materials, eco-friendly fibers, and fair trade production, each piece considers ethical and environmental impacts.

Together, they create an effortlessly stylish outfit that is comfortable and versatile for everyday wear.

Outfit #4 Rock a Sophisticated Look with a Twist

Product List

You mention in your letter that you don’t want to look frumpy or like a hippie, and, as far as I am concerned, this outfit is the antithesis of that; in fact, this sophisticated look is something I would recommend wearing on a night out with friends, or even on a date.

A dusty rose tie-front blouse layered over a silky camisole lends a luxurious feel to a simple pair of flared jeans.

Dainty jewelry, including classy small gold hoops, a delicate bracelet, and a sparkly necklace, provides a modern and elegant way to take your look to the next level. The edgier croc-embossed clutch adds an element of fun to the look.

Finish with some sturdy block-heeled sandals to ground the look.

I hope that these looks have demonstrated that wearing flared or bootcut jeans can be just as chic as wearing skinny jeans! Thank you for your question.

Do you have a fashion question? Send it to us!

Is there something in your closet that you want to wear but have no idea how to style? Do you need advice on what to wear to an upcoming event? Do you have a specific fashion conundrum?

If you have a fashion-related question that you would like to see answered in this column, simply email it to [email protected], and one day you might see your question answered right here on the site!

What do you think?

Do you prefer bootcut or flared jeans over skinny jeans?  How do you like to style your non-skinny jeans?  Where is your favorite place to buy non-skinny jeans?  Let me know in the comments!

If you liked this article about how to style cropped bootcut jeans, then you might want to check out these other picks below – 

1 thought on “How to Style Cropped Bootcut Jeans: Fashion Tips”

    I think for me the key is to have an entire outfit planning, so the jeans look intentional. These aren’t jeans-and-a-tshirt jeans; they’re fashion statement jeans.


Leave a Comment