Just Like That, This "Ugly" Jean-and-Shoe Combo Became Famous


(Image credit: Szymon Brzóska/The Style Stalker)

Knee-high boots could be considered one of the more polarizing shoe trends out there. But while the extra-feeling nature may teeter on the intimidating side (compared to basic booties), celebs and fashion people continue to prove that knee-highs are where it's at this season. While the "traditional" way to style them would be over skinny jeans or with midi dresses, we've been actually spotting A-listers go for a more offbeat—dare we say "ugly"—styling direction…

Yep, you can't thumb through Instagram or scroll through street style snaps without seeing knee-highs worn over baggier jeans. It's definitely more unconventional and seemingly less "streamlined" with the denim bunching out of the top of the boots, but with the rise in popularity of ironic fashion and the industry's disregard for antiquated fashion rules, this vibe totally works. To showcase the famous F/W 19 look, we rounded up a range of women in this forward outfit choice. And naturally, we shopped out the best jeans and boots out there as well.


(Image credit: @songofstyle)

Style tip: Don't be afraid of colored knee-high boots. They'll pop flawlessly against light-wash jeans.


(Image credit: @nnennaechem)

Style tip: Leather on leather is where it's at this season. Try a leather top with jeans and coordinating boots.


(Image credit: Szymon Brzóska/The Style Stalker)

Style tip: Embrace the monochromatic vibe with a black on black-on-black situation.


(Image credit: @gosiaboy)

Style tip: White knee-high boots shine against dark-wash jeans and a black jacket.


(Image credit: Szymon Brzóska/The Style Stalker)

Style tip: Burgundy boots bring an elevated spin to a dark jeans–and-blouse 'fit.


(Image credit: Szymon Brzóska/The Style Stalker)

Style tip: Animal print is still going strong this fall. Test out the trend with your boots, paired with straight-leg jeans and a blazer.


(Image credit: Szymon Brzóska/The Style Stalker)

Style tip: Consider this your new go-to uniform with the white button-down, light straight jeans, and white knee-high boots.


(Image credit: Szymon Brzóska/The Style Stalker)

Style tip: While many of the knee-highs we spot are heeled, flat styles also feel very cool with white jeans.

Next, check out the best basic black boot outfits to try this fall.

Bobby Schuessler
Market Director

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent over seven years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retialers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises. He has also worked across a variety of other media brands and fashion retailers like Refinery29, PureWow, Men's Health, and Gilt covering commerce, trend reporting, women's and men's fashion, home, and lifestyle.