Pairing Jeans and Heels

The classic pairing of jeans and heels is a perennial uniform all women should have in their wardrobe. Moreover, everyone needs a version of this staple look for each season. What I like most about this marriage is its wiggle room for styling — from tailored to rock ‘n roll to feminine, it’s a timeless look that can be dressed up or down to suit all occasions. Here are 5 failproof pairings to keep this look fresh, versatile and chic from autumn through winter:

  1. Jeans + Knee-high Boots
    Stay cozy and classic this winter with skinny jeans tucked into knee-high boots. Try round-toed, block-heeled leather or suede boots, or an over-the-knee version for a statement look that elongates the leg line. Jeans are best kept skinny and high-waisted to balance proportions, then pair with a tailored and tucked crisp white shirt, accent belt and full-length sweater coat to finish the look.

  2. Jeans + Pumps
    A classic Canadian tuxedo — denim on denim — is one of the chicest looks of all time, especially when matched with a classic pump. Either trouser-leg or skinny jeans work for this look when paired with a well-worn chambray shirt to create a sleek, monochromatic column of denim that lengthens. Make sure pumps are pointy, low cut, sky-high and in a “look at me” pop of color or metallic to skew sophisticated and rock ‘n roll, not cowgirl.

  3. Jeans + Kitten Heels
    The feminine kitten heel polishes any outfit, not to mention its low heel offers 24-hour comfort from day to night. Pair with a classic bootleg jean with a sloppy hem roll or clean, wide statement cuff to keep the look cool and current. If kitten heels are slingback, contrast up top with full coverage in a wooly turtleneck and peacoat. If closed-heeled, show some skin with a v-neck sweater and cropped blazer by day, or silk tank and leather bomber jacket by night. Either way, consider adding fishnet knee-highs to keep the look high-style and not cutesy, romantic or too “sweetheart”.

  4. Jeans + Stiletto Booties
    Stiletto booties are a mainstay winter essential for the stylish set. Sexy, chic and date night-ready, they’re the ultimate rock ‘n roll look when paired with boyfriend jeans, a graphic tee and leather moto jacket. For evening, style in all black but mix it up with textures to keep the look interesting and not flat — croc leather clutch, velvet bodysuit, cable knit chunky scarf, faux fur jacket or an over-sized, quilted parka. Boyfriend jeans should be distressed, slouchy and holey with a sloppy rolled cuff.

  5. Jeans + Statement Heels
    When the outfit is about statement heels, make them the star of the show by wearing a high-waisted, cropped ankle-fray jean in neutral black or white. This look is where you can really go for it and take a risk with the heel — python, leopard, metallic, neon, studs, super-sized bow or sparkly embellishments. Then, draw attention to them by popping the same color or pattern somewhere else — belt, jewelry, scarf or clutch. Keep it simple up top with a cropped muscle tee and blazer, or white skinny tank and draped pashmina. Make sure outer layer is cropped or extra long to keep proportions well balanced and chic.

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Elizabeth Kosich Styling