Your Break Between Classes


Let me set the scene:

It’s 5 p.m on Friday and you’re getting ready for a long night out on U Street with your girls. You’re in your silk robe, standing in front of the mirror. You’ve thought about what to wear, but after hours of trying on clothes, tonight’s pre-arranged outfit is just not doing the trick. Back to square one you go. Just as you pull out that one old reliable outfit, you get that text….

“Hey girl are we wearing heels tonight??”

Coordinating with your girlfriends is nothing new in women’s history. For decades, the routine of hitting the town with a group of your ladies has been a posh activity that women look forward to all week. This routine has gained recognition by pop-culture references left and right. “Sex and the City”, “Girlfriends” and “Grown-Ish” all go great lengths to illustrate the importance of a weekly “girls-night-out” trope.

Now, I know we’ve all been here about heels. What do we answer? Does it depend on the vibe of the night? Or does it depend on who you’re going out with? Is it determined by where you are going? Or who’s gonna be there…?

Deciding whether or not to wear heels on a night out can be quite difficult,. but in style just as in math, there’s always a formula. I’m going to take you on my three-step process for choosing if I should wear heels for the night! As “darty (or day party) season” approaches and we’re prepping for more and more social outings, having this guide is essential!


The first step is definitely the most important of them all: “Know Yourself.” This mantra applies to all categories within our life, but most importantly through our fashions. Personal style is subjective, meaning the only person who can understand your style is you.

Be real with yourself. Determine early what appeals to you, and what does not. If you know that every time you wear heels you end up itching to take them off before the night concludes, then that might just be a sign. Test your comfort levels before going out, so that when you’re in a pinch for time you already know what your best bet is.

Let me just make it simple, for you:


  • Don’t Like Heels
  • Can’t Walk in Heels
  • Will Not Make it Through the Night in Heels

THEN DON’T WEAR HEELS! Perhaps opt for something more like a comfortable sandal or kitten heel.


I love step two because it really makes you consider exactly what your sense of style is.

There are two types of people in this world:

  • The Overdressed


  • The Underdressed

Coming from the perspective of someone who is routinely accused of “overdressing,” I truly believe that there is no such thing. That said, regardless of who my audience is, aka the people laying eyes on my outfit that night, I dress in whatever I see fit for the occasion. Be it a feather boa for a casual dinner, a pair of sweats for a museum date, or in this case, heels for a night out with the girls, wearing what floats my boat is all that matters.

For some of us, dressing on the brand to fit the vibe of the occasion is essential. If this sounds like you, you need to pinpoint your environment, and dress according to your perception of it. Researching on TikTok, Instagram, or conducting a simple google search can present you with all the visuals you need to conclude what type of vibe you are walking into. For example, if you’re going to Victory Bar and Lounge in Miami, then you know to expect the latest BBL Couture pictured first (no shade, sometimes we love BBL Couture). But if you’re going to Nobu in Malibu, you may find yourself surrounded by more classy and chic attire like that pictured second. Spot the difference?

Nonetheless, it can be fun to challenge yourself to fluctuate styles based on the environment that you find yourself in. But if you’re anything like me, getting dressed is kind of a daily gamble.

Knowing your audience also relates to having a good idea of the type of ladies that you’re going out with. For example you’re going out with a group of seven women, and you’re the only one who can walk in heels. To keep things balanced, maybe save the heels for another time. But in my humble opinion…  just wear what you feel good in!


This one may be a given, but you have to evaluate what’s in your closet. I recommend that everyone keeps at least two pairs of “go-to” heels that could work with nearly any outfit. More importantly, you need a reliable shoe that screams cute, but also comfort. Spending time with your heels to know which ones are a hit for casual wear, and which ones are only meant for the pictures is a pro tip. Listen to your heels, respect your heels, and most importantly break in your heels before wearing them!

Now that my guide to wearing heels is in your toolkit, I hope you’ve gained a better understanding of yourself and your preferred shoe! To reiterate, always remember to Know Your Style, Know the Vibe, and Know Your Shoe! 

Kynadi Hyde

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