4 Hours of Torture? My Surprisingly Tolerable Personal Styling Session

I've never felt particularly comfortable in my clothes. I hate shopping. I get overwhelmed in department stores, but I desperately needed to update my wardrobe. Determined to find my confidence, I looked into what resources (aside from YouTube) might be helpful. I considered outright paying for a stylist and I almost did until I recalled from a job interview that Nordstrom offers in-house stylists. Nordstrom is quite expensive and outside of my personal tastes, so I looked up other department stores to see if they offered similar services, and it turns out most of them do!

Here's my experience working with a stylist from Macy's!

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If you're on the internet, then you've likely heard or seen Derek Guy (@dieworkwear) discussing fashion and the role of clothes (e.g., what they communicate) within our society. Between my own desire to level up my professional wardrobe, Derek's enlightening content, and wisdom from a handful of women CEOs, I was determined to invest in myself and up my wardrobe.

I didn't grow up with particularly feminine role models, much less ones that put stock into dressing fashionably, and as a result, I was bullied for my lack of style, homemade clothes, and body shape. Looking back, it feels that this particular bullying was pervasive for all young women, but at the time, I felt singled out, and so my confidence in my body and style was so low you could trip on it. It didn't help that until my early 20s, I was so thin everyone I met assumed I had an eating disorder.

I've had moments where I understood myself, the message I wanted to convey, and felt confident in my wardrobe, but the times I have felt insecure far outweigh them. Determined to find my confidence, I looked into what resources (aside from YouTube) might be helpful. I considered outright paying for a stylist and I almost did until I recalled from a job interview that Nordstrom offers in-house stylists. Nordstrom is quite expensive and outside of my personal tastes, so I looked up other department stores to see if they offered similar services, and it turns out most of them do!

Macy’s appeared to be the best fit based on stock and price point so I filled out their online form - https://www.macys.com/s/personal-stylist/. Unfortunately, due to the chaos that is the holidays, I did not get a response back. I didn't want to lose the holiday sale opportunity, so I just went to the store and hoped I could ask for a stylist without an appointment.

I was in luck! As we entered Macy’s there was a sign that mentioned we could ask anybody in the store about working with a stylist. Thankfully, there was a stylist in store and she was available to work with me.

This is where I wish I had documented the process better to share with you, but the stylists have their own office with private dressing rooms. So we could take as many trips around the store as we needed, and my boyfriend could sit on a couch and contribute feedback as I tried things on.

I met with my stylist Rhonda and I told her what I was looking for: a complete wardrobe overhaul. I told her that I worked in the video games industry so I wanted to strike a balance that illustrated who I was, where I am in my career, and the casualness of the video game industry.

I told her that I am easily overheated, preferred not scratchy and breathable fabric, and that I wanted to get out of the habit of wearing so much black.

We took a walk around the store, jumping from designer to designer section. She knew exactly what to pull from each section, quickly gathered my sizes, pulled out things I'd found on the Macy's website, and her own suggestions. Honestly, I was amazed. Every time I'm in a department store, I am immediately overwhelmed, and everything seems to blend together, but not Rhonda.

If I tried something on but needed it in another size she was off in a flash to grab a the right size and was often back within moments.

The part that is hardest to write about is how I felt during this whole process. I felt vulnerable, ashamed, and all around insecure. I was vulnerable because I was admitting that I didn't know how to properly dress myself for success. I was ashamed that I'd waited this long to do something about it. And I felt insecure and raw while trying on the new outfits. I was seeing myself in a whole new light. I physically felt more confident, and it was a new feeling. And to top it all off, I was doing this in front of a stranger and my boyfriend.

I didn’t love everything I tried on and I loved some things that looked awful on but I’m glad I spent the better part of a Saturday with Rhonda.

After four trips around the store and about four hours of trying on a metric fuckton of clothes, I had a whole new wardrobe.

I also learned that:

In total, I spent about $1300 (on a credit card) and I’m glad I didn’t put this experience off because I only paid full price for 4 items (the pinstripe set, purse, and the two belts). The purse was the most expensive thing I bought ($258 + taxes) and it’s my first ever “nice” purse. I plan to keep this purse until I die and I’ll be installing a tracker on it shortly.

After this experience, I’m not sure that I’ll go back to shopping like a “normie" if for no other reason I didn’t have to deal with being overwhelmed by the store itself. I’ll go back to Rhonda later this year once I’ve paid this off to identify a few new dresses. And once I’ve updated my formal wear, my wardrobe will be set for years to come (as long as I take care of the clothes). Sigh. The laundry boss just got a whole lot harder.

If you're on the fence about working with a stylist, I encourage you to start with a stylist at Macy's. You can shop for a single item, an outfit for an occasion, or a whole new wardrobe with a stylist—at no cost to you. It really changed my experience and made updating my wardrobe a lot less stressful because I promise you that if left to my own devices, I'd have bought two or maybe three items that didn't match and left flustered.