What To Wear With Heels: 8 Styling Tips and Outfit Inspiration

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Whoever said heels are for special occasions clearly never wore them with a great pair of jeans. Heels can go with everything, whether you’re grabbing dinner with friends or heading to work, but it can be hard to know how to style them.

In this guide, we’ll show you what to wear with heels for fashionable, versatile, and comfortable daily looks. Read on for eight styling tips that will help you create standout outfits with heels. 

8 helpful tips for casual outfits with heels

These eight tips will help you pair casual clothes with heels:

1. Pair cropped jeans with colored heels

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‍Cropped jeans are perfect for showcasing your favorite heels. Wear brightly colored pumps in hues like red or cobalt blue with light-wash denim for a playful contrast. The shorter length of the denim allows your shoes to steal the show. 

Using our color search filter, you can find colorful heels on ThredUp for less. When you find the perfect pair, complete the look with a tucked-in graphic tee and a structured blazer. A top-handle bag seals the deal. 

2. Combine wedge heels with oversized clothes 

Wedge heels are comfortable and stable—a win-win for everyday wear. Balance their bulk with oversized pieces, like a slouchy sweater or a loose-fitting shirt dress. For example, layer a boxy denim jacket over a neutral dress and add a pair of cork wedge heels. ThredUp’s size filter helps you find oversized styles that flatter your body type without overwhelming your frame.

3. Add high heels to skinny jeans 

High heels with skinny jeans is a classic combination that transitions well from day to night. Opt for neutral-toned stilettos for a polished look or animal print if you prefer something bolder. Roll up the cuffs of the denim to draw more attention to your footwear. 

Add a fitted blouse or a crop top to create a complete outfit. Accessorize with a shoulder bag and, if the weather is cooler, an edgy leather jacket. 

‍Pro tip: Play with different washes of jeans to create everything from monochromatic to colorful looks. 

4. Style denim shorts with block heels 

For warm weather, denim shorts and block heels create a casual but stylish look. Choose mid-length shorts for a contemporary look. Pair the shorts and heels with a loose button-down shirt knotted at the waist, a straw hat, and a tote bag. 

This works with neutral or colorful heels—try a pastel shade if color is your thing. 

5. Pair platform heels with midi skirts 

Platform heels are a foolproof way to dress up a midi skirt. They’re easy to walk in and give you that height you crave. Choose a flowy or pleated midi skirt in a bold pattern or a soft pastel and pair it with complementary neutral-tone platforms. 

This outfit works with a preppy element like a button-down shirt or a simple fitted top tucked in. Add a structured bag for a put-together outfit for anything from casual work meetings to outdoor events. 

6. Wear kitten heels with dresses and skirts

A tailored dress or skirt paired with kitten heels creates an elegant look that’s quick and easy to throw on. If you choose black shoes, you can wear them with any dress you like. Kitten heels are a forever trend, low to the ground and more professional than some higher heels. 

If you’re heading to an important meeting, such as a job interview or work conference, pair kitten heels with a black midi dress and blush blazer. Don’t forget a portfolio bag to tie the outfit. Find your outfit faster with ThredUp’s Size filter, which helps you find items that are sure to fit. 

7. Match slingback pumps with wide-leg pants

Wide-leg pants are an excellent option for dressing heels down. They pair well with slingback pumps, a classic style that belongs in every closet. The sharp look of the shoes perfectly complements the relaxed fit of the pants. 

For an easy outfit, try high-waisted, wide-leg trousers with a tucked-in T-shirt. Add slingbacks in a neutral color like black, and accessorize with a denim jacket and a crossbody bag. 

8. Walk confidently 

Confidence is the secret to making heels work with any outfit. No matter what you’re wearing, walk tall and embrace your personal style to elevate your entire look. Your attitude changes how others perceive your outfit, so practice walking in your heels at home until it feels like second nature, and reach for the most comfortable styles. 

While stilettos and very high heels are fine for some people, many find that wedge, block, and platform heels provide more stability for office days and nights out on the town. 

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Find classy outfits with heels on ThredUp

The right pair of heels can transform any outfit. Whether you’re wearing wedge heels with oversized cardigans or stilettos with skinny jeans, there are endless ways to style your favorite shoes. 

ThredUp makes it easy to refresh your wardrobe with a wide selection of preloved heels at affordable prices. Use our intuitive search filters to find styles that match your vision perfectly, or try our Style Chat feature to shop curated looks inspired by trends, events, and even your favorite celebrity looks. 

‍Explore ThredUp today to find high-quality heels and clothing at up to 90% off typical retail prices. 

FAQs

Can you wear jeans and heels?

It’s not just acceptable to wear jeans and heels—we recommend it! Pairing heels with denim is one of the easiest ways to wear elevated footwear in casual ensembles. Heels work with almost any jeans, from relaxed distressed options to skinny pairs and baggy boyfriend jeans. 

Can you include heels in a capsule wardrobe?

Heels are an excellent addition to a capsule wardrobe. A capsule wardrobe is a curated collection of versatile, timeless pieces you can mix and match to create a variety of outfits. Neutral-toned heels, like black pumps or beige wedges, are classic options that pair well with everything from dresses to trousers. 

Are you supposed to wear socks with high heels?

It depends on the style of the shoe and the outfit you’re wearing them with. If you wear open-toe or strappy heels, skip the socks to keep the look clean. For outfits with closed-toe heels, statement socks or tights create a trendy, fashion-forward vibe you might love. For example, sheer socks with subtle patterns add personality to block heels. Opaque tights work well for monochrome outfits.

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