3 Versatile Denim Styles & How To Wear Them

Head-to-toe outfit picks to help you transition your favourite pair of jeans from summer to fall

Street style photos by Anthea Simms

Street style photos by Anthea Simms



Little in a woman’s wardrobe gets more wear than her favourite pair of jeans. A well-fit, flattering pair will carry her across seasons and even years. Totally multi-functional, jeans can effortlessly be incorporated into a casual outfit or act as an anchor to more playful ensembles. Find inspiration in our outfit picks and get the most from your go-to pair of pants as we move from sunny summer to the fall fashion season.

Below are three staple denim styles (the cigarette pant, the boyfriend fit and the classic blue jean) and some creative ideas for keeping your look current:


The Cigarette Pant

Jeans featured in both looks: Current Elliott ankle skinny in jet black, $178,

Summer Outfit

Take advantage of the warm weather while you still can and pair skinnies with light chiffon shirts and sleek sunglasses. We love the idea of wearing slim-fit denim with graphic black and white ensembles. Chunky-sole oxfords and art-inspired handbags will add something special to your end-of-summer look.

Clockwise from top left: Equipment print chiffon sleeveless blouse, $198, Luella cat eye sunglasses, $70, Opening Ceremony grunge shiny oxfords, $390, Kotur Margo Surrealist printed crepe clutch, $495,

Fall Ensemble

Consider playing with contrasting silhouettes and offset oversized wool coats with cigarette style denim. Bring your favourite jeans into autumn by incorporating of-the-moment prints and patterns. Prominent on the fall runway, a magnified plaid print will keep you looking smart and sophisticated.

Clockwise from top left: Ganni mother of pearl check coat, $447, Giles & Brother bracelet, $135, Nine West grey suede booties, $119,


The (Distressed) Boyfriend Fit

Jeans featured in both looks: Rag & Bone Moss mid-rise boyfriend jeans, $285,

Summer Outfit

‘Casual’ and ‘colourful’ are commonly-used adjectives to describe summer wardrobes; keep the season’s bright spirit alive with graphic tees and costume jewellery in eye-catching electric hues. Mixing and matching prints (we’ve chosen some of the floral and animal variety) with slouchy distressed denim is both fresh and fun.

Clockwise from top left: Christopher Kane shirt, $310, Cuchara ‘Fantasia’ necklace, $248, N.Y.L.A. ‘Jenna Reptile’ flatform sandal, $39,

Fall Ensemble

Try something new this fall and consider wearing relaxed denim styles with more refined, dressy, ensembles for a look that’s daring and different.  Go for the unexpected and pair your menswear-inspired denim with a dusty pink overcoat and some pumps. The outfit plays with masculine and feminine polarities—incorporating both polished and distressed details—in a distinctly modern way.

Clockwise from top left: Zara masculine studio overcoat in pastel pink, $299, Forever New small ivory bag, $50, Topshop light pink heels, $79, Jennifer Meyer for J.Crew triangle necklace in crystal, $298,


The Classic Blue Jean

Jeans featured in both looks: Levi’s straight-leg jeans in blue, $110,

Summer Outfit

Pair your favourite jeans with a laid back summer outfit that’s relaxed and easy. Enjoy the fin-d’été in comfy cotton tanks and neutral accessories with a youthful feel (the perfect accompaniment to the tried-and-true blue jean.) Strappy Scandinavian sandals, a minimalist necklace and graphic sunnies will keep you looking stylish.

Clockwise from top left: Karen Walker ‘Number One’ sunglasses, $329, Acne zone generic cotton tank top, $138, Swedish Hasbeens braided sky high, $170, Made Kebiru triangle pendant necklace, $51,

Fall Ensemble

Gold, burnt orange and caramel colours feel right for fall, especially when worn with a pair of lived-in blue jeans. Reflect the season’s colour palette and choose accessories in warm tones (we’re dying for A.P.C.’s rich burgundy art deco jewellery!) Finish off the look with a luxurious trench coat for an autumn-ready get-up that truly works.

Clockwise from top left: Steven Alan wool trench coat, $495, Alexander McQueen satin stained glass print clutch, $510, A.P.C. art deco ring, $85, and bracelet, $295, Aldo leather ankle boots in Bordeaux, $110,