55 Cool Ways To Style Rolled Up Jeans – The Casual Style’s Favorite

Rolled up jeans provide a casual yet stylish look that’s both trendy and timeless. There are many different ways to style them. But for a much cooler look, you’ll need the right styles that have become a favorite even in the celebrity world. Ranging from the cool ripped style to the casual college wear, there’s a whole lot of options to experiment with. Without further ado, let me introduce you 55 different ideas that will give you that cool look.

# 1 Ripped Style

Add some drama to your casual look with a ripped blue jeans. Pair it with a white t-shirt and army green jacket for that sexy finish.

# 2 Ripped Slim Fit

Get that sexy tapered look with a ripped blue jeans that provides that cool slim fit. Wear the jeans with a white shirt matched with white sneakers. Add a grey sweater and top the whole outfit in a navy cap.

# 3 Side Rip

Settle for a jeans that sports intense rip on one side with a little patchy distress on the other side. Stick in a red handkerchief in the pocket and pair with a beige t-shirt. Finish it in style with a hooded green jacket.

# 4 Black and White Combo

Go for a black jeans that provides a cool casual fit. Pair it with a leather jacket and a white t-shirt. Roll up the jeans to expose the black socks that look good in the white sneakers.

# 5 Ripped College Style

Stand out in a double knee-rip jeans that comes in blue. Pair it with a charcoal grey t-shirt and finish in a two-tone college jacket.

# 6 Ripped Tight Fit

Look cool in a grey jeans that’s ripped on one side. Let it sit tight on the legs and give it the perfect combination of a black t-shirt. Top it in a cool zippered jacket that sports a nice blend of white and black colors.

# 7 White and Blue Combo

Make heads turn in a blue jeans that sports less intense rip. Ditch the socks and wear white sneakers to the feet. Settle for a white pin-dot shirt that’s rolled up to the elbows for that upgraded casual look.

# 8 Autumn Outfit

Embrace the day in a cadet jeans that sport a slim-fit design with a cool rips. Match it with camouflage green boots to the feet and a grey t-shirt. Settle for a green jacket that sports accents of black and grey.

# 9 Cool Fray

Make it frayed on the roll with a cool ripped design to match. Let it stand out by pairing with a three-piece jacket that provides a cool modern fit. Add a black pocket square and finish in a white vest.

# 10 Faded Style

Wear blue jeans that sport that cool faded look. Wear it tight on the legs and top with a beige jacket that’s got lots of pockets to serve you while on the move. Put on Chelsea boots to the feet and complete everything in black bracelets.

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# 11 Travel Style

Go for a cool ripped jeans that sports a faded blue color. Pair it with a Tommy Jeans t-shirt and take your luggage along for that perfect traveler style. This outfit looks great when finished with Adidas shoes to the feet.

# 12 Going Simple

Settle for a slight roll up in a dark blue jeans. Give it the perfect complement of a charcoal grey sweater that sports pulled-up sleeves to expose that cool brown bracelet with metallic accents.

# 13 Casual Upgrade

Upgrade your casual style a little bit more with a blue jeans that’s made to sit tight on the legs. Add a black leather belt to it and wear that snow white shirt to add some sparkle to your outfit. Finish in style with a black slim-fit jacket and a pair of dark sunglasses.

# 14 Simple Street Style

Rock the streets in a tight fitting jeans that sports that cool blue pigment color. Wear it with a pin-stripe t-shirt that’s topped with a black hooded sweater and a sky blue jean jacket.

# 15 Perfect Roll-Up

Go for a cool roll-up, both to your ripped blue jeans and to the sleeves of your snow white shirt. Match with a brown belt and light brown leather luggage for that perfect traveler style.

# 16 Basic Street Style

Make it ripped with that cool blue color to match. Add some drama by sporting that faded look. Match the jeans in a grey long-sleeve sweater and a classic timepiece to the wrist. Take along your black leather jacket to create a perfect complement.

# 17 On-Point Wear

Go for ripped denim pants secured with a blue fabric belt. Add a long sleeve snow white shirt and a timepiece to the wrist. Settle for a blue stripped waistcoat and flip over your grey jacket for that cool finish.

# 18 Black and Charcoal Grey Combo

Settle for black ripped pants. Ditch the socks and put on a charcoal grey t-shirt. Embrace the cold weather in style by finishing off with a black weather jacket that sports that sexy quilted design.

# 19 Winter Wear

Brave the cold weather in slim-fit pants sporting that pigmented blue color. Add tough brown leather boots to the feet. Get some warmth in a green woolen jacket with a beige shawl wrapped around the neck. Add a green t-shirt on the inside for that cool finish.

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# 20 Fresh Denim Outfit

Go fresh in a ripped denim jeans paired with a denim jacket. Roll up the sleeves of the jacket and match with a white t-shirt. Finish with a pair of rubber shoes to the feet.

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# 21 Professional Style

Create some professional looks with a dark blue slim-fit jean pants. Sport that faded look at the front for that creative contrast. Pair it with a checkered shirt that comes in black and white.

# 22 Upgraded Street Style

Go for an upgraded style in a ripped jean pants. Let it stand out on the tattooed skin. Pair with a white t-shirt that sports a cool “V” neckline. Finish with sport shoes on the feet and remember to ditch the socks.

# 23 White Lee – Blue Jeans

Settle for a ripped blue jean pants sporting that faded look at the front. Top it in a white Lee t-shirt and add wear a classic timepiece to the wrist.

# 24 Clean Casual Outfit

Go clean in blue jean pants paired with a black t-shirt. Settle for a silver necklace with a bracelet on the wrist. Finish in style with a cool pair of sunglasses. What you get is a tough yet sexy look that will make you stand out from the crowd.

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# 25 The Cool Tatter

Keep it clean and simple with a sky blue jean pants. Pair it with a tattered shirt that comes in a cool electric blue color. Go for black shoes and ditch the socks to upgrade your casual style a step further.

# 26 Preppy Casual

Go for a neat casual style that complements your sleek haircut. Settle for blue jean pants with some sneakers on the feet. Go for a slight fade at the front and give it the perfect match of a brown sweater. Add a buttoned-up white shirt on the inside to make everything look neat and fresh. This is an outfit that looks a bit more on the classic side.

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# 27 Perfect Street Style Combo

Go for multiple colors to complement your ripped blue jean pants. Go for some white sneakers that sport black stripes and ditch the socks. Add a wide neck black t-shirt and top everything in a hat. Take along a brown leather luggage for that sweet street style look that’s simply dope and on point.

# 28 Creative Ripped Style

Ditch the conventional rip style and go for a creative rip in your blue jean pants. Give it that patterned look and match with a black sweater and black hat. Add some sparkle into this outfit with a glowing timepiece on the wrist to make everything stand out.

# 29 Grey and White Street Style

Look cool in a grey jean pants that sports that sexy ripped design. Top it with a snow white shirt and a charcoal grey sweater. Give it more edge by finishing with a grey trench coat that gives you something to warm up to in the cold weather.

# 30 Sexy Designer Outfit

Go casual in a ripped jean pants that sports that worn out look. Take this cool look a notch higher by combining with a wide neck designer t-shirt that sports a multi-colored look.

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# 31 Fashion Swag

Settle for grey color in a tight fitting jean pants. Let it sport a uniform color without any fades. Match it in style with a white logo-imprinted Levis t-shirt that sports a shallow “V” neck. Go buttonless in a checkered red and black shirt ensuring to roll up the sleeves for a more casual look. Finish by going sock-less in black sneakers.

# 32 Jean Pants with Boots

Sport a tough look with a cool pair of black leather boots to the feet. Let the cuffed part of your sky blue jean pants rest over the top of the boots. Sport in some faded look in the jeans to create that cool bleached effect. Complete the outfit in a beige jacket and a checkered white and red shirt.

# 33 Evening-Out Wear

Look cool and stay comfortable in the cold evening weather. Do this with a pair of dark blue jeans that hugs tight on the skin. Settle for some warmth with a dark grey trench coat and grey neck scarf. Match your blue pants with a sky blue shirt.

# 34 Cool Weekend Wear

Get a perfect outfit that make’s for a great weekend. The trick is to go dark and do it in style. Settle for dark blue jean pants and match with a straight-neck navy sweater. Go for some extra warmth with a black trench coat and a white lapel pin that blends with the sparkling watch on the wrist.

# 35 Bleached Street Style

Go for a faded pair of blue jeans that create the illusion of a bleached fabric. Get the bleached look that perfect match of snow white sneakers and a white t-shirt. Put on a dark blue coat and a brown knitted scarf to help you brave the cold weather.

# 36 Capped Style

Sport that slight fade in your blue pants sporting that casual fit with tapered legs. Pair the pants with a red t-shirt that sits snugly on the neck. Add a beige jacket that sports black collars and black cuffs. Top this cool casual style in a navy cap.

# 37 Trendy Street Style

Go for a new trendy look that will make heads turn as you walk the streets. Go for blue ripped pants that sport cool patch fades. Make it trendy with a pin-dot blue and white t-shirt sporting rolled up sleeves to the elbow. Go partly button-less and add some sneakers on the feet. Finish in a classic watch and bracelet.

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# 38 Gentleman Style

Settle for a dapper ripped design making it tapered on the legs. Let it sport that faded look that matches with a white designer t-shirt. Go for multi-colored bracelets to add some fun to your outfit. Give it some extra style with a modern luggage case that looks simply dapper.

# 39 Adventurous Wear

Love to go for some adventurous exploration? A tough outfit might just be what you’re looking for. And there’s nothing tougher than a pair of denim pants. Make it stand out in a dark blue shade that sports that uniform pigment. Add to its toughness with a brown leather belt. Give this tough combo the perfect match of a light blue shirt that’s left partly unbuttoned. Go for a slight roll up on the long sleeves finished with a scarf to the head. Take your camera gear along and be ready to take some shot.

# 40 Dark Wear

Go dark and do it in style. Settle for dark jean pants that sport straight legs. Let the pants sit flush with a black shirt that’s topped with a black jacket. Add a black cap on the head for that cool match. Take your camera with you and get the ultimate photographic experience in your camouflaged outfit.

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Rolled up jeans are a perfect way of going casual in style. It’s an outfit that adds some toughness to your looks without being too sophisticated. Even though it’s a popular style for the young generation, older people have the chance to also join in the flow. Try it to keep everything tough, simple and casual.

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55 Cool Ways To Style Rolled Up Jeans – The Casual Style’s Favorite

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