how to wear heels casually with everyday outfits

Have you ever looked longingly at a pair of heels that you knew would look so good with your outfit but questioned whether they were “too dressy” or “too formal” for the occasion? Or do you just long to wear heels more often but you don’t know how to incorporate them into your style without looking too formal. I want to help you learn how to wear heels casually and more often, with a few tips on how to wear them everyday if you really want to.

I am quite tall already (5’8”) and I’m used to wearing heels only at special occasions and nights out, so I set out to overcome my hesitation to wear heels more casually and learn to be comfortable wearing them more often and for more informal occasions. It’s done wonders for my confidence, my own sense of style and has helped me to look more polished and put together on the regular. 

Is it weird to wear heels casually?

Generally, heels are considered a dressy shoe worn at formal occasions to look more professional, feminine, sexy or glamorous. This is why it may look strange to wear certain types of heels in casual situations. But wearing heels casually is neither weird nor normal because it depends on multiple factors. 

The most common reason women hesitate to wear heels casually is because it looks too professional, sexy or glamorous in the wrong setting. While it’s important to learn to wear anything you want with confidence, I think it’s equally important to learn how to judge the situation and be tasteful with your style.

how to wear heels casually nude stiletto heel on grass
how to wear heels casually wedge heels summer picnic heels for grass

For example, wearing a 3 inch stiletto heel to a picnic in the park with friends could be considered weird because it will be extremely hard to walk on grass making you uncomfortable and therefore your friends uncomfortable as well. In this situation, a wedge heel would be more balanced because the wider surface area will make it much more easy to walk on grass and the cork or straw materials that wedge heels are usually made of would give a really nice summery aesthetic to suit the occasion.

How to wear heels casually

As a general rule the higher and thinner the actual heel of the shoe is, the more it’s associated with formal footwear for situations where women want to look more feminine, sexy or glamorous. 

A good way to avoid feeling overdressed when wearing heels is to opt for either a high block heel or a low stiletto heel (ie. kitten heel). Finding a balance between heel height and heel type (eg. stiletto, block, wedge) is a good initial rule to help you wear heels casually in any given situation.

how to wear heels casually high block heels casual outfit
how to wear heels casually low stiletto think kitten heel casual outfit

To a lesser extent, shoe type (eg. open or closed toe) and shoe texture (eg. patent leather or cork) can help you to find shoes that are more suited to casual occasions. Closed pointy toed shoes are considered more formal than open toe sandals but they can work depending on the rest of your outfit. 

The sheen of patent leather can usually give a very professional look but you can counteract this by choosing a more subtle colors like nude or beige. You could also opt for more casual looking textured shoes like suede, matt leather, cork or wood. With these more general guidelines out of the way, let’s look at how you can actually wear a pair of proper heels casually.

Skin tone colors

how to wear heels casually subtle colors nude beige neutral high heel outfit
how to wear heels casually subtle colors brown neutral high heel outfit black stylish woman

Skin tone or neutral color heels are a great way to soften the formal look of heels because they blend in so smoothly. This works best if you’re wearing cropped pants or a skirt that shoes a bit of leg because you want to see a bit of that skin color for this to work well. Another great thing about this is that it can work with open sandal heels and more formal pointy stilettos as well.

Make it the feature

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how to wear heels casually statement leopard print heels casual sweater outfit

You don’t necessarily have to hide your heels or camouflage them when you want to wear them casually either. You could choose to make a statement of them by keeping your outfit really relaxed and simple but choosing a nice bright color or and interesting print to make it the feature of your outfits. This is a very cool way to show some of your personality and make your causal heeled outfit look intentional and fun.

Keep it simple but classy

how to wear heels casually keep outfit simple but classy white shirt
how to wear heels casually keep outfit simple but classy high heel outfit black turtleneck

Black pointy stilettos are perhaps the hardest shoe to dress casually because they are so associated with professional wear. The way to make this shoe work casually is to keep a bit of that professional vibe throughout the rest of the outfit but make it very relaxed and simplified. This helps to create a look that’s classy and polished but not “dressy” or formal. Try to incorporate some more relaxed textures as well like denim for example to tone down the corporate vibe. 

Dress them down

how to wear heels casually dress down your heels athletic wear outfit with heel
how to wear heels casually dress down your heels athletic wear outfit with heel selena red tracksuit

Some athletic and lounge wear can work really well with heels. It’s a nice go to casual outfit for running errands or traveling. If you’re trying this look, pay close attention that your outfit still looks presentable and your clothes don’t have any rips, stains or creases. This casual heeled outfit is not about looking messy but rather elevating your casual clothes so that they look intentional and put together.

Hide your heel

how to wear heels casually hide the heel long trouser outfit
how to wear heels casually hide your heels with long flowy skirt outfit

This look is for you if you want a bit of height in your casual outfits but don’t necessarily want to reveal that you’re wearing heels. You can conceal your heel with wide leg pants that have a sleek drop or a long floaty skirt. The idea here is to remove the heels visually from the whole look and just concentrate on the rest of the outfit. It’s a great way to get that elevation and feminine feel while minimizing the formal effect that heels have. 


how to wear heels casually oversized outfit
how to wear heels casually oversized outfit jeans

This can be a very cute and comfortable way to wear heels casually. Similar to the dressing down technique, it’s important to make sure you’re clothes are well kept because this look works best when your clothes look intentionally oversized, not baggy, poorly fitted or messy. With this look you have a lot more flexibility with the types of clothing you can pair with your heels as the oversized technique is an effective way to make formal clothing like blazers and office trousers look more relaxed. 

Is it OK to wear heels with jeans?

how to wear heels casually with denim outfit katie holmes
how to wear heels casually with denim jumpsuit outfit

Jeans of all types are another great way to make heels look more casual. This is because denim as a material itself has a rustic, laid back look to it and if you choose it as the main material for your whole outfit you can get away with more vibrant, eye-catching heels as well as more traditional office style shoe. Denim has the ability to make heel wearing look effortless and there are so many ways to incorporate the material into your outfit so if you like it denim then this is a very versatile way to wear heels casually.

Block & Wedge

how to wear heels casually high wedge casual heels for everyday outfits
how to wear heels casually high block casual heels for everyday outfits

And of course there is the option to focus on wearing heels that actually look more casual. Block heels and wedges are great because you can get away with having quite a high heel because they’re much less formal and “glam” looking than the traditional stiletto type heels. They work so well for summer outfits especially with open toes sandals and wedges made of natural materials like wood, cork and canvas. If you do decide to pick up a few more block type heels for your wardrobe, opt for more traditional styles rather the trendier heels as this will allow you to wear them longer than just a season or two. 

How often should you wear heels?

As I’ve started to incorporate more heels into outfits more often, I’ve been curious about the impact on my feet and back so I asked my podiatrist how often I should be wearing heels and here is what he recommended. Heels can be worn on a daily basis provided you take care to make sure they’re comfortable and you don’t wear them for very long periods of time without breaks.  

How often you should wear heels depends on height, structure, and support. Low heels (1.5 inches or shorter) should be worn up to 4 hours a day, medium heels (1.5 – 3 inches) up to 3 hours a day and high heels (3.5 inches or more) around 1-2 hours a day. 

how to wear heels casually how long should you wear heels heel placement

Heels that are placed right at the back edge of the shoe tend to push all of your weight onto the ball of your foot, so instead try to wear heels that are placed under the center of your heel as this will help to distribute the weight more evenly. 

how to wear heels casually how long should you wear heels weight distribution

Ensure there are no gaps between the arches of your feet and the shoe bed. Instead you can use insoles in these areas or have them stitched directly into your shoe so that your weight is distributed throughout your whole foot.

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Close-toed shoes can provide better support than open-toe but make sure that there is enough space for your toes and the lip of the leather does not press into your knuckles as this is a high friction area. Use silicone pads if necessary.

how to wear heels casually how long should you wear heels ankle straps foot grip

Slide on and slip in heels are quite fatiguing for the foot because you have to hold onto them by the toes. Ankle straps secure the shoe to your foot without the need to hold on so your feet will not tire as easily. 

Can you wear heels casually everyday?

Depending on your lifestyle, you can wear heels casually everyday if you want to, especially if you mix and match the height and type of heel you wear. However, it’s important to pay close attention to your foot health as wearing heels constantly can result in damage to your feet. 

If you plan to wear heels daily, it’s a good idea to see a podiatrist and have regular checks on your feet to make sure everything is fine. It’s important to note that wearing heels casually does not mean you need to wear them everyday or to every casual event that happens. You can gradually incorporate heels into your daily wardrobe  for specific casual occasions where you still want to make an effort and this will help you to find what works best for your lifestyle. 

There are ladies who love their heels and will wear them every single day for different reasons, such as looking professional, or simply their love for heels. It really just boils down to your personal style and works best for you. Here are some tricks that can help you optimise your comfort while wearing heels for long periods of time so that you can start wearing them more often or even daily.

how to wear heels casually everyday foot doctor protect your feet podiatrist

How to wear heels casually everyday?

If you want to start wearing heels casually everyday there are some things you need to take into consideration to help you wear your heels on a daily basis. These tips will help you to be able to wear your heels comfortably throughout the day and prolong the amount of days you can wear them as well. 

It’s always good to take a break from wearing heels and there are plenty of other gorgeous shoes that can still enhance your style without a heel, so please don’t feel like you have to wear them everyday if you would prefer not to. These tips can also help you if you just want to wear heels occasionally as well. 

Related: What to wear if you can’t wear heels.

Perfect your walk

Learning to walk correctly in heels is essential to being able to wear them more often. Heels with ankle straps or anything that fixes the shoe more securely to your foot will also go a long way to prolonging wear time as your foot can become quickly fatigued in slip on shoes that are held on by the toes.

There are three basic principles that can help you walk correctly in heels. Balance is often overlooked but it’s essential to walking well in heels. Improving your core strength or practising yoga postures for balance will really benefit your walk especially if you do this consistently and make it part of your lifestyle. It will help you to find your centre of gravity which is different for everyone and develop strength in your feet and legs which can also help to lengthen how long you can wear your heels for.

how to wear heels casually three important keys to walking in heels for a long time

Next is making sure your weight is mostly distributed through your heels and not just dumped on your toes or the balls of your feet. When you step your heel should hit the ground first with a soft bend in the knee. This helps to maintain a straight posture from your heel to your head rather than feeling pushed forward by the heels, making you bend over your toes. 

The final basic principle is to protect the most vulnerable parts of your foot that are exposed to high friction like the back of the heel, the inside big toe knuckle and the ball of the foot. We all know how hard it is to walk when you have even a tiny pebble in your shoe, so making sure you have no pain is crucial to having a good walk. Transparent gel cushions are discreet and provide a thick buffer for your skin. Gel cushions also provide a bit of suspension to help reduce impact of walking on hard surfaces for your joints.

Never wear a new pair of heels for a long period of time fresh out of the box, it’s vital that you break them in properly so you don’t put your feet through hell. This testing period will also help you to figure out if you need insoles, toe separators or ankle guards to protect your skin and give your feet all the support they need throughout the day. 

how to wear heels casually everyday comfort protect skin

Double down on TLC

A good amount of tender loving care towards your feet is always recommended not only as a thank you for helping you look fabulous but to also prep them for the next time you wear your heels. Foot stretches are excellent for keeping the muscles in your feet flexible and supple and helps your foot health by releasing any tension that has built up throughout the day. 

Another effective method is the “golf ball” massage which is great for stimulating circulation and relaxes tight muscles. For maximum effect you should do at least 10 mins of stretching/rolling after a warm foot soak and follow up with a high quality moisturising cream that can sink into your skin overnight. 

Here’s how I perform a golf ball massage after a foot soak:
  1. Place a golf ball on a yoga mat beside a wall, you can also use a towel, carpet or any other surface that won’t just allow the ball to slip and roll away.
  2. You can sit if you want a lighter massage, but I prefer to stand and use the wall for balance as this allows me to apply more of my body weight for a deeper massage which is more effective. 
  3. Remove shoes and socks and roll the ball under one foot applying moderate pressure.
  4. Roll the ball along the length of your foot from your heel to your toes and then from the outer edges to the inside all the way down along the foot. 
  5. Next focus on the ball of your foot and the base of your toes. You can use circular strokes or a back and forth movement, just find what feels good.
  6. Finally repeat the same strokes around the heel and when you find a sore or tender spot you can work on it a bit more. 
  7. It’s important to do the massage on both feet.
how to wear heels casually everyday tlc foot massage golf ball

Craft Confidence

One of the most important aspects of making heels look casual and effortless, is confidence. This comes with feeling comfortable with the shoe you’re in and learning to walk well in them. You can always start slow and gradually increase the heel height and type so that you can get used to your new aesthetic.

Don’t be afraid to film yourself walking in your heels as well from different angles so that you can analyse what your heels are doing to your overall posture from an outside perspective. It will help you to correct minor issues like overly bent or flexed knees, leaning too far forward or back or looking down too much etc. 

It’s important to remember that a lot of the hesitation of wearing heels comes from uncertainty of how you look in them and what they’re actually contributing to your style. The more you work on perfecting your walk, comfort and overall sense of style in your heels the more confident you will become in wearing them whenever you want. 

Related: Do you get used to heels
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Whether you’re hesitant about looking too overdressed, or you’re just researching some casual outfit ideas that work great with heels then I hope you have found this helpful. I would love to see how you use the tips in this article to enhance your style so please please tag me on Instagram, Tiktok or Pinterest or you can or send me a message because I would love to see! 

About the author 

Mish has a Masters in Fine Art and she’s passionate about classical design, history and culture. She loves to analyze fashion and style through this lens to help people develop authentic personal style.