5 Jeans with Heels Outfits for All Occasions 

That pair of blue jeans in your closet may be the most dependable item of clothing you own, but they’re far from basic. From wide-leg to skinny (not to mention your ripped jeans and bedazzled options), there are plenty of ways to elevate this staple. One of our favorites? 

Throw on a pair of heels.

Whether you choose slingbacks or cork heels, the footwear you step into can set the tone for the rest of your denim-inspired look. To start your styling adventure, you’ll first need to discover all the possibilities this fashion fusion has to offer.

Let’s explore 5 different ways you can style your jeans with heels outfits. 

#1 Make it All About the Ankle Strap

Feminine and playful, heels with ankle straps go perfectly with cropped, wide-leg jeans, and those occasions when you want to feel flirty and carefree, like a picnic in the park. 

Why the crop, you ask? Well, when you’ve got strappy heels, you’ll want to show them off. Cropped, wide-leg jeans place all the emphasis on your ankle. For an extra elongating look, try a pair of jeans with a high-rise waist. 

If the ankle strap on your heel is colored, try tying the color into the rest of your outfit. For example, if you have a pink ankle strap, a pink shirt or a contrasting color can make this detail pop, leaving you with a cute outfit pulled together by a nice pair of heels.

From Day to Night

There’s more than one way to style this lively look. If you’re going to a casual afternoon event, these additional style elements will fit the setting:

  • A fluttery, cropped blouse 
  • A pair of dangly, statement earrings
  • Hair down and relaxed

If it's date night at your favorite restaurant, dress up your look with:

  • A sequined or sparkly top
  • A leather jacket
  • A topknot

#2 Easy Sophistication

If you’re looking for a combination suitable for the office and other professional settings, try pairing Majorca Cutout Sandals with cigarette jeans. A perfect compromise between skinny jeans and straight-cuts, cigarette jeans are fitted through the knee, then fall straight to the ankle. 

To complete this sophisticated pairing, try:

  • A button-down blouse or oxford shirt
  • A blazer or cropped cotton jacket
  • A bold pattern or bright color

From Day to Night

You can easily take the cigarette jean and cut-out heel combination out to the bar or a live music event after work. To spice up your outfit, try these transformations:

  • Add a swipe of red lipstick
  • Swap your work bag for a quilted leather mini-purse or clutch
  • Throw on a belted overcoat or trench for another layer

#3 Try Fresh and Modern Cutouts

There’s nothing more versatile than a pair of cutout heels and a pair of skinny jeans. For all-day comfort, pick a pair of skinny jeans with stretch. 

Instead of a block color or a neutral, experiment with cutout heels that feature a fresh pattern, such as an abstracted take on animal print. This attention-grabbing style will be sure to turn heads. 

To complement the bold shapes created by your cutout heels, accessorize with some geometric jewelry.

From Day to Night

Whether you’re taking a trip to the modern art museum or rocking out at a concert, you can style this combination to match. 

For a night of music and dancing, add:

  • A silky tank top with lace detail
  • Sparkly, shoulder-brushing earrings

For a more artsy vibe, pair your jeans and heels with:

  • A slouchy beanie
  • A knit cardigan

#4 Choose Chunky Heels for a Retro Appeal

When you think of vintage fashion, chunky-soled shoes might be one of the first options to come to mind. To pay homage to previous decades, try pairing your jeans with chunky cork heels that feature a prominent ankle buckle. 

Some possible denim pairings include:

  • High-waisted jeans with an acid wash for an 80s nod
  • Jeans with a pleated front for a 90s throwback

Break out your own vintage denim—or look through your mom’s dresser—for the perfect pair of jeans to complement chunky, cork-soled heels. 

From Day to Night

To dress up this retro style, you need only look back a few decades. For a comfy-casual outfit, pair your denim with a 70s-inspired crochet shirt or poncho. For a laid-back evening out, evoke the 90s with an understated and form-fitting black top under an oversized flannel.

#5 Free Up Your Toes 

Need an effortless, step-in-and-go style? The peep-toe mule heel is the answer. This shoe offers a streamlined silhouette while letting your toes breathe. With no straps or buckles to slow you down, you’ll feel extra free to try out every kind of denim with your jeans outfit idea.

Some possible jeans to pair with your mule heels include:

  • A pair of bell-bottom or flare jeans
  • Some mid-rise straight jeans
  • A pair of loose, distressed boyfriend jeans

From Day to Night

Thanks to their versatile style, mule heels offer plenty of opportunities to dress them up or down. For a more bohemian feel that can suit anything from a lunch with friends to a casual work meeting, try:

  • A pair of denim with frayed hems
  • A loose, flowy kimono or silk wrap
  • A few bangles on your wrists

For a more professional setting, or for an evening that demands a bit more polish, you can easily dress up your mules with:

  • A ruffled wrap top
  • A tan trench coat
  • A black tote bag

Style from the Heel Up with TOMS

One of the best ways to approach an outfit is to start with one element and let it guide your following choices. Our suggestion? Start with your heels, and let them spark inspiration for everything from your denim to your accessories.

TOMS has a variety of women’s heels to suit any ensemble. Whether you opt for slingbacks or a chunky sole, you can elevate your jeans and your style with the perfect pair of heels.

For heels that inspire style day or night, shop TOMS.

Reviewed By Andrew David Stewart

Andrew David Stewart is the Manager of Digital Marketing at TOMS and has been working in the digital marketing and social media world for 6 years. Andrew is a lover of nature and the outdoors, and is passionate about telling stories through digital media.


Cosmopolitan. 20 Types of Jeans You Need to Live Your Best Life. https://www.cosmopolitan.com/style-beauty/fashion/g26429319/types-of-jeans/

Fashion Magazine. How to Wear Cigarette Jeans: 13 Best Outfit Ideas. https://fmag.com/how-to-wear-cigarette-jeans/