The Cuffing Season: 25 Stylish Outfits With Cuffed Jeans

By Kaia Saunders / December 7, 2016
Three outfits with cuffed jeans

We love the casual yet trendy look of cuffed jeans. Whether it’s the sleek sophistication of elegantly cuffed skinny jeans or the more relaxed boyfriend style, one thing’s for sure: this season is all about cuff jeans.

Look to the runways of Paris, New York and Milan and you’re sure to find models sporting this definitive trend for fall. In fact, with denim being so versatile, this is one fashion style that is made for just about every season.

But probably the best part about this trend is that, when it comes to cuffing jeans, the sky is the limit. You’re free to style them however you see fit; the only barrier is the heights of your creativity. To keep things fresh and modern, though, here are a few style pointers to bear in mind:

  • When cuffing jeans, rather stick to skinny, straight leg or boyfriend jeans. Flared and bootleg jeans, because of their bell-bottomed shape, can make your legs look larger than they actually are.
  • The length of your cuff jeans is all-important. Aim for the area closest to your ankles – cuff them too high and it may look like you’re wearing pedal pushers from the 1950s.
  • Don’t cuff the hems of your jeans too much. The most stylish width is between one and two inches. When in doubt, go for a smaller cuff over a very wide one.
  • One golden rule: remember your body proportions when choosing jeans. If your cuffed jeans are baggy, choose a fitted top. And vice versa – skinny cuffed jeans look great with a loose, flowing top.
  • We’ve rounded up some fashion inspiration on how to cuff jeans of all shapes and styles – from cuffed skinny jeans to advice on how to cuff boyfriend jeans. Choose your favorite style and get cuffing!

Cuffs and Neutrals

1) Beige Beauty

Woman in cuffed skinny jeans and beige top with a bicycle next to a lake

Snakeskin sandals add some edge to this outfit of layered neutrals (photo: lalavo.com)

Here is a modern look with a touch of old luxury. The simple elegance of classic beige and gold accessories gets a trendy upgrade by wearing cuffed skinny jeans. Edgy snakeskin strapped sandals add to the relaxed and easy sophistication – the perfect lesson in how to cuff jeans beautifully.

2) Winter White

Woman wearing cuffed jeans and a white shirt with nude shoes and a brown handbag

The pure elegance of classic blue and white is given a modern twist with edgy cuffed jeans (photo: thedarlingdetail.com)

White is always a winner with denim, and even more so when it comes to cuff jeans. These straight leg jeans are given a single wide cuff below the ankle – a great way to draw attention to gorgeous heels in a classic yet simple way. The look is completed with minimal jewelry, reflective gold aviator sunglasses and a tan carry-all tote bag.

3) Wrapped Up in Wool

Woman in cuffed skinny jeans and wool sweater with nude strappy sandals

Cooler temperatures call for thick, luxurious fabrics like this chunky woolen jersey (photo: omgoutfitideas.com)

Play with different textures and fabrics to create an eclectic, modern look that shows off your curves. These distressed skinny jeans are ripped in subtle places along the legs as well as right on the cuff. This brings the eye right down the legs, ending in unexpectedly sexy strappy nude heels.

The emphasis on the legs means that the upper half of the body can be luxuriously wrapped in thick winter wool. This outfit is great for long-legged girls with a smaller bust, looking to add some weight on top.

4) Grey Hound

Woman in cuffed skinny jeans and grey turtleneck sweater with grey stilettos on the street

Cover up from head to toe in layers of denim, striped linen and wool (photo: brooklynblonde.com)

This cuff is barely noticeable but oh what a difference it makes. Think of it as another layer added to this multi-dimensional ensemble. With these skinny jeans ripped dramatically on the knee, the slight single cuff brings some structure while also focusing the eye downwards to the feet. A striped button-down shirt peeps out beneath a grey oversized turtleneck sweater – a must-have look for the cooler months.

Blazing Beauty

5) Fitted Fashion

Woman in cuffed boyfriend jeans together with a black fitted blazer and black stiletto heels

Keep it cuffed yet elegant with slouchy cuffed jeans and a tailored black blazer (photo: indulgy.com)

If you’re looking for a style lesson on how to cuff jeans in the most elegant way possible, this right here is your answer. This outfit shows off a slightly baggy-fitting boyfriend style but, cuffed right on the ankle and combined with pointy Christian Louboutin stiletto heels, the effect is sleek and very glamorous.

Worn with a fitted black blazer also casually cuffed at the elbow, this ensemble is casual, trendy and super elegant.

6) Brogue Basics

Woman in the park wearing blue cuffed boyfriend jeans with brown brogue shoes and a black military style jacket

Preppy brogue shoes take the spotlight when paired with edgy cuffed boyfriend jeans (photo: seventhandgrind.wordpress.com)

Easy does it when learning how to cuff boyfriend jeans. This ripped distressed style is given a haphazard, uneven cuff right on the ankle – the perfect choice to show off these men-style brown brogues. To shine a further spotlight on the prep school style, throw on layers of neutral-colored T-shirts rounded off with a structured military-style jacket and a large leather tote bag.

7) Chic in the City

Woman on the streets of the city in blue cuffed skinny jeans with a loose silk shirt and white blazer

Choose soft, floaty fabrics to bring class and femininity to your distressed skinny jeans (photo: nadyana.com)

These cuffed skinny jeans do wonders to add style and sophistication to this ensemble. Combine the sheer beauty of a white silk blouse and white blazer with blue denim and tan accessories for a chic and elegant city persona. With this look, a neat, solid cuff creates a classy effect.

8) Radiantly Red

Jamie Chung in blue cuffed boyfriend jeans together with a statement white T-shirt and red blazer

A flash of red creates an instant style statement next to ripped cuffed jeans (photo: whowhatwear.co.uk)

Jamie Chung’s ensemble is a master class in how to cuff boyfriend jeans. Her choice is a pair of straight cut denims with distressed ripped detailing, ending in carefully shaped wide cuffs. A simple white statement T-shirt ups the cool factor, not to mention an unexpected flash of red in her blazer.

Coats and Cover Ups

9) Layered and Cuffed

A woman in blue skinny jeans cuffed at the ankles with white trainers and a long beige coat

Simplicity is the order of the day when layering multiple neutral fabrics (photo: www.closetfulofclothes.com)

This look is all about layers in carefully selected neutral shades. These slim fitting straight leg jeans are cuffed one time only – a nod to the easy simplicity of the jeans-and-sneakers look. A longer length white T-shirt is concealed by a navy blue sweater, all pulled together with a cover-all beige coat.

10) Neat and Tidy

Woman wearing blue skinny jeans with a white T-shirt, long black cardigan and black strappy shoes

Classic accessories shine against the monochrome background of black and white (photo: victoriatornegren.se)

Monochrome colors come alive in this sleek, streamlined ensemble. These cuffed skinny jeans from Asos are fitted to perfection, including neatly folded cuffs just above the ankle. Dainty black strappy heels become the star of the show, accentuated beautifully by a longer length black cardigan.

Round off the look with chic black sunglasses and Chanel’s classic quilted lambskin Westminster Pearl flap bag.

11) Comfortably Chic

Woman wearing ripped and cuffed skinny jeans with a white T-shirt and long grey cardigan, together with beige ankle booties

Ripped jeans add to the laissez-faire attitude of this comfortable daytime look (photo: lolajeannine.com)

If comfort is your main aim, you can’t go wrong with this relaxed weekend look. The star of the show?

Cuffed skinny jeans casually ripped along the thigh and knee area. To keep that crisp, carefree look, go for a pair of beige suede booties – the ideal accessory for this neutral-inspired ensemble. A soft brushed cotton T-shirt is knotted at the waist and worn under a snug ankle-length grey cardigan.

Above the Ankle Cuffs

12) Off the Cuff

Woman in jeans cuffed above the ankle
Jeans cuffed above the ankle (photo: fforyou.com)

The one rule about cuffed jeans is simply that there are no rules. Look at the outfit above. Woman wears dark denim jeans with a lighter cuff right above the ankle. She opts for a striped top beautifully accessorized with graphic print and a bright statement handbag.

13) Gingham Glam

Sarah Jessica Parker wearing skinny cuffed blue jeans together with a blue-and-white gingham shirt and pointy white stiletto shoes

The country staple of gingham fabric is given a city upgrade when paired with cuffed skinny jeans (photo: thefashiontag.com)

These cuffed skinny jeans tick all the style boxes without trying too hard. Here, Sarah Jessica Parker’s stonewashed jeans are cuffed unevenly above the ankle and though it may be less noticeable, looks sensational. A simple gingham plaid button-down shirt is given a chic upgrade with the eye drawn downward to her white stiletto heels.

14) Model Muse

Karlie Kloss wearing blue cuffed jeans together with a black T-shirt and black leather jacket

Black leather and stiletto heels combine to create an edgy chic city ensemble (photo: teenvogue.com)

Spotted on the streets of the Big Apple, model Karlie Kloss is the picture of New York City chic. Wearing subtly fitted boyfriend jeans, the hems are cuffed just above the ankle to show off dainty black pointed stiletto heels. Adding edge to the ensemble is a slim fitting basic black T-shirt and trendy leather jacket.

15) Beguiling Boho

Rosie Huntington-Whitely wearing cuffed boyfriend jeans with a white long back vest and nude strappy sandals

Baggy boyfriend jeans become instantly elegant when paired with nude heels and modern accessories (photo: tstyledme.com)

These cuffed jeans on Rosie Huntington-Whitely have a sexy bohemian feeling to them – that casual, just-rolled-out-of-bed vibe so popular with street style stars. Add to it a cheeky sliver of skin along the midriff and the effect is cool, hip and ultra-trendy. To add height and a touch of class, complete the outfit with nude ankle-strap sandals for a look fit for the stars.

A Pop of Color

16) Color Frenzy

Woman wearing cuffed boyfriend jeans together with a bright green shirt and black strappy sandals

Go quirky and one-of-a-kind with a standout item in an unexpectedly bright color (photo: tstyledme.com)

The way you cuff your jeans can totally determine the tone and style of your outfit. Case in point: these cuffed boyfriend jeans on style blogger Julie Sariñana. Her cuff jeans have single folds arranged in a slapdash manner – perfect for crafting a creative, bohemian feel. Add to this an artistic lime green button-down blouse and the overall effect is carefree and easy-going.

17) It Was All Yellow

Woman in the city wearing ripped blue jeans, a striped T-shirt and a brown leather jacket together with pointy leopard-print heels

A bright yellow wrap scarf adds warmth to this cozy fall outfit (photo: fabfashionfix.com)

Straight leg jeans are great for showing off long limbs. Add cheeky rips on the knees combined with slightly uneven cuffs and the effect is sleek and streamlined, even when combined with Breton stripes on top. Create a dash of color by adding on a bright scarf to go with your color palette; in this case, rich mustard brings out the warmth of a brown leather jacket and leopard-print pointy heels.

18) Cerise Tease

Woman wearing blue cuffed jeans together with a faux fur top and cerise ankle boots

Cuffed jeans get a creative twist with faux fur and eye-catching ankle boots (photo: bloomgirlblog.com)

Make an eye-catching accessory the focal point of your outfit, like these vivid cerise ankle booties. Combine these with skinny jeans cuffed elegantly above the ankle; the lighter shade of these folded over cuffs matching the color of a wrap-style faux-fur top to perfection. This combination is quirky and creative – the ideal choice when you’re keen to make a subtle style statement.

19) Plaid Poise

Woman wearing cuffed blue jeans with a plaid shirt and brown strappy sandals

Make statement heels the focal point of a simple jeans-and-shirt fall outfit (photo: sazan.me)

If there’s a sexy pair of statement heels that you’re dying to show off, you can’t go wrong with cuffed skinny jeans folded neatly right as the strap hits the ankle. No need to accessorize too heavily either – throw on an easy button-down plaid shirt with a simple sling handbag and you’re good to go.

Denim Top to Toe

20) Dungaree Diva

Woman wearing blue denim dungarees with a white vest and black Mary Jane shoes

The 90s dungaree is back on trend thanks to edgy cuffed hems (photo: galknows.com)

Maybe it’s a throwback to the girl groups of the 90s but denim overalls are making a big comeback this season. Breathe new life into your trusty style staple of yesteryear by rolling up your cuffs like a true street style star.

Here we see wider-leg distressed boyfriend overalls folded in a loose, casual style. Showing a bit of skin on the ankle adds a sexy spin while, instead of the usual Converse sneakers we’re accustomed to seeing, dainty Many Jane shoes create an unexpected girly touch.

21) Denim Deluxe

Woman on the city streets wearing black ripped denim jeans and blue denim shirt with black strappy sandals

Layers of denim combine into one relaxed but classy street look (photo: victoriatornegren.se)

This look is all about sleek denim in different cuts and colors. What sets this ensemble apart though is the darker denim jeans, creating a cuff in the same color as the main fabric.

Cuffed in a single fold just above the ankle, this draws the eye down towards black strappy sandals. While the bottom half of the body is kept straight and slim-fitting, the top can be loose-flowing and voluminous, so adding an unusual silhouette that’s modern and bang on trend.

Casually Cuffed

22) Off Duty Denim

Woman in blue cuffed skinny jeans together with a grey T-shirt and black leather jacket

Simple and understated separates combine into a laidback sporty ensemble (photo: femalejungle.com)

Street style can be elegant while casual at the same time, as seen in this modern look centered around dark-wash denims. In an outfit combining neutral separates, we see cuffed skinny jeans paired with black patent leather slip-on shoes. A slightly longer grey T-shirt matched with a black zip-detailed jacket complete this slick, laid-back ensemble.

23) Saturday Style

Woman in the city wearing cuffed boyfriend jeans with Converse sneakers, a white T-shirt and patterned bomber jacket

The season’s coolest bomber jacket becomes fun and playful when worn with cuffed jeans and Converse (photo: aelida.com)

This off-duty ensemble is perfect for a casual Saturday where comfort and cool are high on the agenda. Loose-fitting boyfriend jeans are cuffed evenly on both legs, paired with easy grey Converse trainers. Up top, we find a slouchy T-shirt tucked in under a bomber jacket patterned in black and white print.

24) Peekaboo Fashion

Woman on the sidewalk wearing ripped blue skinny cuffed jeans with a white T-shirt and nude pointy heels

Cute and playful on top meets sleek and polished down below (photo: amandoblogs.com)

Elegant meets casual in this ensemble. Slim-fitting skinny jeans are perfectly cuffed slightly above the ankle, with nude pointy heels further elongating the legs and adding height. To get that sleek, polished effect in your cuff jeans, lightly iron the cuffs to flatten them and streamline the entire look. A cheeky white T-shirt and funky patterned clutch purse add a touch of fun and whimsy to the ensemble.

25) Casual Chic

Selena Gomez wearing ripped boyfriend jeans together with a black T-shirt, black fitted blazer and black pointy stiletto heels

Boyfriend jeans get the Hollywood treatment as Selena Gomez hits the streets in stiletto heels (photo: blog.styleestate.com)

These jeans on Selena Gomez show us exactly how to cuff large, baggy styles of jeans. Here the hems of her jeans are cuffed ever so casually in big messy folds. This gives her hips and tiny waist more shape and definition. Then there’s the position of the cuff – falling right above her slim ankles, the wide legged cuff gives a sexy glimpse of skin, ending beautifully in pointy stiletto heels.