Did Spending Half a Grand on Clothes Help Me Overcome My Fear of Spending Money?

Ever since releasing Heal Your Relationship with Money, I’ve experienced a number of newer and more nuanced connections with money that I wanted to share with you in the hope you’ll be able to make more sense of your ever-changing relationship with your coins.

Understanding Fear and How to Overcome It

We all have fears.  Fear of public speaking. Fear of intimacy. Fear of rejection. Fear of bugs. You name it, there’s a fear around it.  When it comes to overcoming most fears, the most common advice is to face it, head on. 

But a fear of spending on wants and fun? That’s a unique fear to have in a society characterized by the pleasure principle.  A fear of spending is so uncommon that it was difficult for me to find articles or even sympathy for this issue.  Most people think that this fear is a good problem to have and will ensure a life of happiness and wealth.

But I can tell you that it doesn’t. It creates a world of financial paranoia and tightness that only grows worse with each new dollar saved.

Without any outside guidance, I listened to my inner voice and ultimately decided that the best way to overcome a fear of spending was to throw some money at it. In particular, I decided to indulge in one of my closely held fantasies—hiring a personal stylist to have a private fitting session based on my burgeoning attention to fashion. (I’ll write a different post on how you can do it, too, for less than you expect.)

Trunk Club, Pinterest, and Dropping $549 in an Hour

Once I booked the session with The Trunk Club, a high-end online styling service which take appointments in their Madison Avenue location, I became surprisingly excited about what the experience would bring.

On a deeper level, I was in awe of the woman that I was becoming before my very eyes—the kind of woman that stated what she wanted, owned her desires, and went after what she wanted no matter how extravagant or unpopular it was.

It was like I was shedding skin.

And an afternoon of shopping for clothes for my emerging self seemed apropos.

Prior to meeting with my stylist Hannah, we had been in communication via Pinterest. I used Pinterest to collect and organize all of my style wants into one place. I shared all of my ideas and questions with her.

Even taking the time to think about what I like to wear was an amazing experience— patterns around my taste started to emerge, making it easier for me to identify what I liked and what I didn’t like so much more quickly. 

What my Pinterest board showed was that my style was a mix of edgy, feminine, minimalist, and glamour and I couldn’t wait to see some clothes to match all of the personal growth and development that was going on within.

When I finally met Hannah, she took me on a tour of the space and then we got to the business of trying on the collection she had curated for me.

The fitting lasted over an hour and I learned so many tips and fashion basics that gave me life. Here are three.

  1. I learned about how flattering the French tuck can be for brown girls blessed with ample booty, but don’t want to keep homeboy or homegirl in the next cubicle from doing their work. (i.e. you get to accentuate the waist without giving them a show from behind).
  2. Off the shoulder, cowl necks, and boat necks look great on me. Also, cable knits work for me.
  3. I can do a lot with color: cherry red and ice blue are bae for me.

Most of the items that Hannah brought out were nice, but I fell in love with three of them—a motorcycle jacket and two blouses which totaled over $549 when all was said and done.


To be honest, I had NEVER spent $500 on anything related to my wardrobe. Ever. I could only justify that type of expenditure on the cost of college textbooks, a plane ticket, or housing (a.k.a. needs), but not clothes (a.k.a. wants).

I, however, didn’t let the fear overcome me because I had a mission. I had walked into Trunk Club with a goal—to buy what I wanted if I saw something that I loved. Well,  I walked out of Trunk Club with those beloved items and something more—a whirlwind of emotion about what I had.just.done.

Buyer’s Remorse Kicks In… Sorta

I texted a girlfriend immediately: She was proud of me because she knew my journey with the clenched first. I called my mom and she, too, was happy for me. I was proving to myself and others that money wasn’t controlling me, I was controlling it: “See, World, I not only save big, but I also can spend big when I want to and not have regrets.”

Take that.

The regrets and remorse didn’t come right away, but they did come.

It took me forever to remove the two blouses from the shopping bag and put them in my closet.  Same for the leather jacket.

I even went to my best friend Google to find cheaper alternatives for all of the items I bought before I learned the biggest lesson of my Trunk Club experience: Spending a lot of money on yourself doesn’t equate with self-care. Identifying your desires, honoring them, and addressing them does; money is just a tool to support that goal.

In my case, I needed to use money as a tool to give myself the gift of a personal stylist and fitting session. This desire wasn’t a whim. I had wanted this experience for myself for close to five years. I had budgeted for it. I had made time for it on my calendar. I would see no rational reason for me to deny myself this experience unless I wanted to consciously hold on to the limiting belief, “Buying nice things for yourself is selfish” or “there is nobility is deprivation.”

So Trunk Club: Yay or Nah?

So the bottomline: If I had to do it all again, I would absolutely book a private styling session at Trunk Club, not because it was expensive but because it was something that I wanted to do for myself.

The only thing I’d leave behind was all of the production: calling in a lifeline, telling my mama, and telling the whole damn world I bought something expensive that I liked that was in my budget.

But I’m smarter, wiser, and have a healthier relationship with money now.

So next time there will be no need.

Frugal Feministas: Let me know what you think. What experiences have you had with being afraid to spend money? What’s your story?

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