How to Wear Heels Casually

There’s no question heels elevate any look – pun intended. They transform what could be considered a relaxed, casual outfit into a polished, ready-for-a-night-out ensemble. I’ve always found the best way to wear heels casually is by finding that right pair of pumps you can walk in as if you had sneakers on. Tough I know, but nothing’s worse than seeing a girl struggle in heels – it takes the “casual” right out of the equation if you ask me.

   Once you’ve mastered the walk, there’s definitely some tips you can keep in mind when trying to achieve that effortless feel. Keep reading for my three tips on how to wear heels casually.

ilse livelearnluxeit gray longline cardigan
ilse livelearnluxeit blogger teal pointed toe heel long gray cardigan

Gray Longline Cardigan: Similar HERE and HERE || Chambray Shirt: Similar HERE and HERE || Black High-Waisted Jeans: The best HERE || Teal Pointed-Toe Heels: Similar HERE and HERE || Black Chain-Trim Crossbody: Similar HERE and HERE

ilse livelearnluxeit long gray sweater and chambray shirt

ilse livelearnluxeit longline cardigan teal heels
ilse livelearnluxeit blogger in demin tshirt and gray cardigan

ilse livelearnluxeit blogger black high waisted pants long gray cardigan
ilse livelearnluxeit blogger in longline gray cardigan sweater

ilse livelearnluxeit long gray cardigan demin shirt
ilse livelearnluxeit blogger forever 21 black satchel

ilse livelearnluxeit fashion blogger
ilse livelearnluxeit blogger in express chambray top

ilse livelearnluxeit blogger teal pointed toe heels


Nothing screams “laid-back” more than a pair of jeans. Pop on a pair of your favorite heels and you’ve got yourself the perfect casual outfit. This combo works because jeans help you feel relaxed and comfortable and the right heels (I’m loving these teal ones at the moment) add just a tinge of style.


If you want to wear heels casually, the clothing should be kept super simple – the more “basic” the better. Let’s say you switched the heels in this look for a pair of slide-on sneakers (you guys know these are my faves)? You’d get an outfit fit for running errands.

Another way to keep it simple is by going monochromatic and letting the heels stand out. It helps the vibe stay super easygoing and informal.


There’s a fine line between wearing a loose hoodie or sweater and just throwing on workout clothes. I would love to see yoga pants work with heels but sadly, it ain’t happening. If you really want to stretch the “casual” in “wearing heels casually” then opt for sleek, opaque leggings/jeggings. The extra inches from the pumps and the form-fitting silhouette of leggings will create the perfect mix of comfort and chic-ness.

ilse livelearnluxeit blogger how to wear heels casually
ilse livelearnluxeit long gray cardigan

 If I had to pick my favorite go-to look for night’s out it would definitely be this. I love how simple yet on-trend you can be without really trying. Heels are magical like that 😉

What tips do you have when wearing heels – in casual or formal settings? Let me know in the comments section below.

Happy Monday!