How to wear denim shorts: 15 Style Panel tips for braving this often-feared basic

How to Wear Denim Shorts Style Panel
How to Wear Denim Shorts Style Panel

Much like the classic LBD and the plain white T, denim shorts rank high on the list of timeless trends. Feared by some, loved by many, the versatility of this wardrobe staple makes this classic style a must-have for summer.

On the streets, we’ve seen trendsetters brace the warmer temperatures in denim shorts of all shapes and colours. From music-goers at Coachella to Toronto’s stylish park devotees it seems there ain’t nothing like a pair of Daisy Dukes to stay cool and fashion-forward under the hot summer sun. The warm weather trend has long been a hit with fashion darling Alexa Chung, whose ability to dress her cutoffs up with heels and a structured jacket and down with a classic plaid shirt, shows us just how flexible these breezy blues can be.

In the fashion world, denim shorts were thrown onto the high-end scene in 2010 when models clad in itty-bitty versions of the style strutted down the runway at Balmain, turning a head or two along the way. Following our Spring 2013 style guide, shorts are back on-trend with denim versions making several runway appearances on the Spring 2013 runways. Dsquared² showed us how to wear denim shorts at their spring show, with runway models pairing their cutoffs with layers of gold chains. DKNY dressed Cara Delevingne in loose, boyfriend-style denim shorts on its Spring 2013 runway, offering a more conservative take on the typically pint-sized style.

Not sold yet? We’ve turned to our style panel for advice on how to wear denim shorts this summer.

I’m a Little’s Alexandra Nikolajev is a professed jean short addict, who recommends DIY-ing your denim thrift shop finds for cost-effective shorts tailored to your body type. Dainty Girl’s Nicole Wilson finds most denim cutoffs too short. In answering the question how to wear denim shorts, Wilson’s rule of thumb is too avoid all styles where the pocket lining is longer than the shorts. In terms of colour and print Short PresentsKayla Short loves the printed denim trend citing bold prints as a great way to add oomph to your denim shorts.

How to Wear Denim Shorts Alexandra Nikolajev

Alexandra Nikolajev, 27
Toronto | I’m a Little

I am a jean short addict. While I’ve purchased countless pairs in the past, I’ve recently become addicted to DIY-ing my denim with thrift shop finds. It’s cost-effective and simple + fast to complete, plus you can tailor the fit and length to your body. I love the ripped denim look of this white pair I crafted and simply paired it with with a seasonally trendy chambray shirt and a crisp white pair of runners for a clean summer look. If DIY is not your thing then I always recommend buying high-waisted denim to give the instant appearance of longer legs and I typically buy my denim a size or two bigger as I prefer them loose-fitting. Jean shorts are a summer staple so I definitely recommend you get in on the trend!

How to Wear Denim Shorts Whitney Cosgrave

Whitney Cosgrave, 25
Los Angeles Via Vancouver | See Shop Eat Do

The jean short can definitely be a tricky thing to wear. I’ve found that for me, the best style is not too low, not too short, and typically cuffed rather than a frayed edge. I love to pair mine with classic pieces to keep my look from being too casual, and so that they are dressed up enough to transition easily from day to night.

Whitney’s Wearing: Sunglasses, Made Eyewear. Denim shorts, Ann Taylor Loft.

How to Wear Denim Shorts Cee Fardoe

Cee Fardoe, 27
Paris Via Vancouver | Coco and Vera

A good pair of denim shorts is hard to find. I know – I hung onto my beloved pair from seventh grade, purchased in the kids’ section at Zellers, for almost ten years because I couldn’t find a suitable replacement. No matter how many pairs I tried on, none seemed to work for me; some were too tight, some were too long, some were way too short. I think anyone can pull off denim shorts; there is a pair out there to suit you no matter your shape and size. But you’re much less likely to find the pair if you don’t know what you’re looking for. Before you go out on a mission to find denim shorts, do a little research; summer issues of magazines are full of denim shorts in every cut and colour. Even a quick flip through one or two issues will give you a much better idea of what kind of denim shorts you like – and which ones you’d be better off just leaving on the rack! Personally, I finally found my perfect pair, mid-length and loose through the waist and thigh, at American Eagle. Denim shorts are a bit more casual than my normal everyday outfits, so I like to pair them with a pretty tee and heels for a bit of added elegance.

Cee’s Wearing: T-Shirt, Twist & Tango. Shorts, American Eagle. Heels, ASOS. Necklace, Delphine Pariente. Sunglasses, Ray-Ban.

How to Wear Denim Shorts Stephanie Koch

Stephanie Koch, 27
Kelowna Via Calgary | Inherited Jeans

This summer I am loving the printed short; prints on silk for a dressier look, and printed denim for an update on the classic combo of jeans and a t-shirt. I like to soften up these camo shorts with a pastel top and delicate jewellery, for a simple summer outfit that’s cute, and practical for hot weather.

Stephanie’s Wearing: Shorts, Billabong. T-shirt, Wilfred. Sandals, Michael by Michael Kors. Sunglasses, Joe Fresh. Waist Bag, Hipsters for Sisters.

How to Wear Denim Shorts Lyndsey Forest

Lyndsey Forest, 23
Edmonton | Over My Styled Body

Your summer wardrobe just wouldn’t be complete without a pair of denim shorts! They are such a great staple to have because you can dress them up or keep them casual, whatever you’re in the mood for! So when you’re looking to invest in a pair I would suggest going for a high waisted fit as it is flattering on every body type. The high waist helps hold everything in place and keeps your backside looking pretty fabulous! Now I’d say that’s a winning summer combo.

Lyndsey’s Wearing: Shorts, Forever 21. Belt, H&M. Top, J.Crew. Clutch, J.Crew. Bracelets, J.Crew. Heels, Just Fab. Sunglasses, J.Crew.

How to Wear Denim Shorts Nicole Wilson

Nicole Wilson, 29
Toronto | Dainty Girl

Outside of housework or walking the dog, I haven’t really worn jean shorts since high school. It’s not that I don’t like them, I just feel really self-conscious in them! After Jessica Simpson donned her Daisy Dukes in 2005, denim cut-offs became way too short for any self-respecting woman – if the pocket lining is longer than the shorts, you won’t catch me wearing them! For this Style Panel challenge, I found a pair that is short, without the bleavage (bum cleavage).

I love these polka dot cut-offs because they don’t look like your typical pair of jean shorts. They sit low on the hip, the denim is soft and they fit loosely in the leg for comfort. The length and relaxed shape of the blouse alleviates the self-conscious factor for me. I think every outfit needs balance and since I’m showing a lot of leg, I wouldn’t pair these jean shorts with a crop top or a low cut blouse.

I’ll admit it, the hoards of teens and tweens in bleavage-baring shorts totally turned me off jean shorts for a while, but I’m glad I added these to my summer wardrobe and I promise to keep it dainty!

Nicole’s Wearing: Shorts, GAP. Blouse, M for Mendocino. Bag, Sneha Varma. Necklace, House of Harlow. Bracelet, Ann Taylor. Shoes and Sunglasses, Aldo.

How to Wear Denim Shorts Kayla Short

Kayla Short, 26
Halifax | Short Presents

Upon first glance these tropical printed shorts might not look appropriate for a denim challenge. However, don’t let their crazy print fool you, because these shorts are definitely denim.

Printed denim, as you may have noticed, was a huge trend for spring. The bold were rewarded this year when it came to pant bottoms; from leopard print jeans to full on floral, there was a plethora of options for adding a little oomph to your outfit. Capitalizing on the crazy pant trend, it has now spilled on over into summer wear as well, offering more fun and character to an otherwise practical item. These statement-making bottoms are the perfect way to spruce up a basic tee or your favourite Oxford (as seen here). Simply pile on a couple of accessories and you are good to go.

These shorts from Old Navy combine practicality, comfort and a little tropical print to boot, and therefore, they are a win in my books. For an instant sartorial face-lift, opt for printed denim shorts.

Kayla’s Wearing: Printed Shorts, Old Navy. Blouse, Suzy Sheer. Denim Tote, Old Navy. Necklace, Olive + Piper. Wedges, Mudd via Kohls.

How to Wear Denim Shorts Cara McLeay

Cara McLeay, 28
Vancouver | A Fashion Love Affair

Cut off denim is my go-to in the summer months… as much as I love a good summer dress, jean shorts can be worn for more activities, and can be dressed up easily to go from day to night with a simple pair of pumps

Cara’s Wearing: Top, J.Crew. Shorts, American Eagle. Heels, Zara. Clutch, Rebecca Minkoff.

How to Wear Denim Shorts Amber Desilets

Amber Desilets, 30
London | Canadian Fashionista

I do believe everyone can wear shorts, its just about finding that perfect fit for your body type. Since I’m a little shorter than average, I tend to go with a shorter short as it gives the illusion of longer legs, I then throw on a pair of heels for a little extra height to complete my look. My favourite way to style denim shorts in the summer is to pair it with a pop of colour in my shirt, add a blazer so I’m not showing too much skin all at once and then a pair it will a killer pair of heels. This is a great way to rock your jean shorts this summer without looking like a teeny bopper and it also takes you from day to night in one easy swoop.

Amber’s Wearing: Top, Le Chateau. Blazer, H&M. Sunglasses, Oakley Backhand. Necklace, Cocoa Jewelry. Belt, Smart Set. Shorts, American Eagle. Shoes, Aldo.

How to Wear Denim Shorts Jacquelyn Son

Jacquelyn Son, 21
Vancouver | Style Worthwhile

Jean shorts are one of my go-to bottoms to wear in the summer. I love all styles: high-waisted, coloured, printed, etc. But my favourite ones are destroyed cut-offs. They’re fun and easy to match. You can dress them up with a pair of heels and a blazer or casually wear them to the beach in a bikini and sandals.

Jacquelyn’s Wearing: Blazer, Astar’s Womens Clothing. Jean Shorts, American Eagle. Tank, Zara.

How to Wear Denim Shorts Sandy Joe Karpetz

Sandy Joe Karpetz, 25
Edmonton | The Pretty Secrets

Jean shorts are an easy staple to fall back on. Rather than stick to the same old I like to take my denim a step further by customizing vintage pairs of high waisted jeans. Firstly, I cut them down to the perfect short short length and fray the ends. Then, depending on my mood, I make them into bleachies and add a few studs. With crop tops dominating this summer, I like to keep the waistline high on my shorts to balance it out.

Sandy’s Wearing: Top, vintage. Shorts, The Pretty Secrets DIY. Platforms, Zara. Purse, vintage. Sunglasses, Nordstrom.

How to Wear Denim Shorts Leah Gust
Photography by Peter Chatterton

Leah Gust, 31
Toronto | Leah Says

Last summer was my first summer wardrobe in many, many years to include shorts and it wasn’t so bad! Once my legs became reacquainted with the light of day I really got into the look. This summer I’m updating my regular Levis denim cutoffs with the 90s throwback, overalls! Certainly not the most flattering item, they are nonetheless super comfy and help me test the limits of my fashion comfort zone – something I try to do every season. Overall shorts are much easier to wear and style than full overalls because the bare legs add a healthy dose of femininity to an otherwise male work wear look. I’ve worn a simple tank but could also have worn a sleeveless denim shirt with combat boots to really relive the grunge glory days! Unlike regular cutoffs that can be worn year round with the addition of tights, your overall shorts are really only here for the summer so get ’em on and enjoy all the extra pocket space!

Leah’s Wearing: Overalls, vintage from Penny Arcade. Sunglasses, Brick Lane in London. Tank, H&M. Sandals, Office.

How to Wear Denim Shorts Barbara Ann Solomon
Photography by Trevor Negin

Barbara Ann Solomon, 26
Toronto | Barbara Ann’s Style Blog

The most basic summer essential, the denim short, can be worn in so many ways. Just like their longer counterparts, the jean short can be dressed up or kept casual, and the styles seem to change seasonally.

This season, I’ve been pairing my boyfriend-style cut-off Levi’s with crop tops, keeping this look casual. Shorts remind me of my childhood summers at camp, so I layer on the bracelets. The shoes could really make or break this outfit; a pair of flats or thongs might seem too casual, but an easy summer wedge seems perfect for any occasion.

Barbara Ann’s Wearing: Top, Velvet by Graham and Spencer. Shorts, Levi’s. Belt, vintage. Wedges, Browns. Bracelets, gifts. Beaded Bracelets, Club Monaco. Red Cuff, vintage.

How to Wear Denim Shorts Becky Kung

Becky Kung, 30
Calgary | Velvet & Vino

Jeans shorts are everything this season! One of the popular looks is the cut-off short which can be found in all shapes and colors. I especially adore the special accents we are seeing on jean shorts such as leather pockets seen in this pair and also coloured denim jeans.

The key to styling this look is first and foremost about knowing your body shape. If you aren’t comfortable with revealing your full legs I recommend wearing a longer version of jean shorts that extends closer to the knee. Another great option is the high-waist jean shorts, which are also a fun season trend and perfect to disguise any mid-waist problem areas. All these options allow for any body-shape to enjoy the jean short!

Becky’s Wearing: Shorts, Forever 21. Chiffon Blouse, J for Justify. Wedges, Le Chateau. Bracelet, Joe Fresh.

How to Wear Denim Shorts Kassandra Camponi

Kassandra Camponi, 26
Edmonton | Kastles

Jean cut offs have quickly become my obsession this summer. I thrifted a few pairs of jeans & did a little cutting & DIY action to turn them into cut offs. I made sure to cut them so they weren’t too short. They are great for kicking around in at the but also perfect for dressing up. I love the contrast of the rips & tears mixed with my heels & blazer. If stripes & florals are a little too much, start off with a black blazer & a striped tee. It is an outfit that can easily transition from day to night with a shoe & bag switch.

Kassandra’s Wearing: Denim shorts, Levi’s DIY. Top, Joe Fresh. Blazer, Joe Fresh. Necklaces, Bitchin Beads and Forever 21. Heels, Forever 21.