What It’s Like To Work With A Stylist

Ever stood in front of a crowded wardrobe thinking, “I have nothing to wear!” If that doesn’t describe you at some point in life, please teach me your ways. For the rest of us, this is a common scenario. A few years ago, before Marie Kondo fever descended upon us all, I hired a stylist to help me clean out my closet and update my look.

Why would I do this? Well, I’m a huge believer in efficiency and skill specialization. Why would I spend hours doing something poorly when I can pay someone to do it quickly and much better? Calculating the value of my time (opportunity cost of hours spent) helps me understand when I should outsource and when I should do something myself.

But I digress- as someone who prefers Money magazine to any fashion mag featuring weight challenged teens modeling clothes I couldn’t possibly fit into or afford, I thought the expertise of someone who could tell me what looked good based on my body type would go a long way in simplifying my closet, boosting my confidence, and saving me time.

Thinking, “Maybe I should hire a stylist?”

The first stylist I worked with four years ago came as a referral from a fashionista friend. She floated into my apartment that spring day wearing gold Jimmy Choo heels and a flowy skirt, with the perfect beautiful blonde blowout. Her size 0 dress size should’ve been an indication that we might have issues understanding each other (my body type is… let’s say “ethnic”). However, that day, filled with the possibility of feeling fabulous I welcomed her into my home, help her set up her collapsible clothing rack near my closet, and prepared the ominous black garbage bags of clothes we would give away.

For the next two hours, we sped through hanging up “keepers”- things that I love that fit me well and the “maybes”- items we would consider at the end and tossing the ever increasing “no’s” we would donate and sell.

She taught me about the importance of belts and accessories to differentiate outfits (I had almost none) and wondered about my prevalence of flowery dresses (I had way too many).

At the end, we probably had at least 5–7 garbage bags of clothes to sell and donate, spanning junior high clothes, high school, college and beyond. My newly fashionable 25 year old self was looking forward to going shopping with her to fill the gaps for my wardrobe, which was now about 50% emptier. I believe this service cost about $150–200 or so dollars for two hours (this was 2012).

The next session we had, my stylist pulled a bunch of clothes for me at different stores. The associates all knew her and had my clothes waiting for me in dressing rooms. Theoretically, it would have been an amazing timesaver and super fun to walk in and feel fabulous trying on personally handpicked clothes. Almost like some sort of rom com transformation scene.

In reality, none of the clothes she picked out fit me. Styling herself and other size 0 models meant that she wasn’t able to translate her fabulousness into my body type. The blazers were too short, the dresses ill fitting, and even the accessories fell flat. I came away with one dress, a jean jacket, and a couple of belts.

More importantly, I felt awful. Going shopping is not something I do for fun- clothes generally don’t fit me, I don’t like spending money, and like most women who grow up in Western society, I have body issues. Having a gorgeous stylist pick out clothes for you that don’t fit is ten times worse since you’re actually paying for the negative experience.

We parted on good terms. She didn’t charge me for the less than ideal shopping experience, and I took away a lot of learnings from the wardrobe clean out that I applied over the next few years. For example, she taught me that I should walk into my closet and feel like it’s my favorite store. Things should be organized by color, and all hangers should be uniform.

Fast forward to last month.

My closet was once again getting out of control and I thought to try again with a different stylist. I looked up a well recommended stylist on Yelp and filled out her online questionnaire about my style goals and body type. Her specialty was in business wear and dressing professional women. While I don’t need to follow any dress codes for work, who doesn’t want to look polished and put together? HEYO- Almost 30 here, gotta start dressing the part.

She came over with her clothing rack and we commenced a similar closet breakdown. Her philosophy was more about brands, fabric types and fit. She gave me recommendations not to have embellishments near my hips which would accentuate the wrong parts, and made faces touching most of my clothes because they “felt cheap.” Along the way, I tried to learn what this “cheap” feeling was, but I suspect it had more to do with finding out the brand was not designer. I lamented my previous stylist shopping experience, and she promised this time it would be different. I was cautiously optimistic. This time, I donated 5 bags of clothes (where do all these clothes come from anyway?!?) and my closet felt emptyish again. This stylist was more expensive and charged $275 for the closet cleanup. I ended up paying $350 because she stayed a bit longer.

While the first stylist took me to a handful of stores of varying price levels, this one met me at Nordstrom’s. She picked out a bunch of clothes ahead of time as expected, and I walked in one weekday evening after a tough day at work hoping to have some fun.

As soon as I saw the clothes she picked out, I knew automatically they were wrong for my body. Though I promised her an open mind, every single thing I tried on didn’t fit me. She had thrown away my cardigans promising better ones that didn’t “feel cheap” but instead there were dowdy grandma-like cardigans that were 2–3x the cost of the ones she had thrown out. We went through her selection in about 15 minutes and I was legitimately fighting back tears.

Now, there’s a big difference between 25 year old me and 29 year old me. The younger self was much more impressionable, not surprisingly. The present takes no bullshit and abhors wasting time (and money). When the stylist recommended we potentially go shopping elsewhere, I told her the value wasn’t me standing in the dressing room while she picked out clothes but coming in and having options that would work already. My time is valuable, and picking out clothes that don’t fit me is something that I actually do really well myself (for free!). I recommended we reschedule and she apologized profusely saying this had never happened to her before (although she had seen my entire closet and seen me basically try all my clothes on before we went shopping). She then proceeded to charge me another $275.

And that’s when I lost it. My mom called me and I just exploded in tears. My mom was so confused until she realized what exactly was going on. “Idiot!,” she said like any immigrant matriarch. “You were PAYING someone to make you feel bad?? I will take you shopping FOR FREE and pick out all your clothes. You know what works best for your body and you should be the one shopping for yourself. Don’t pay someone to force their personal style on you! Stop being ridiculous and save your money!”

She was 100% right. I felt so bad about myself, I lost sight of the fact that the problem wasn’t me…it was the fact that neither of my two stylists (blonde, skinny, all-American) knew my style or my body.

While in theory, the stylist process should have saved me time and money, all it did was cause me to have self loathing and waste my time. No thanks.

So buyer beware: I’d still cautiously recommend a stylist to help you clean out your closet (they will expedite the process exponentially because they will help you remove whatever emotional attachment you have to your clothing). However, the shopping process is a complete and utter waste of time.

Now, I may not have found my perfect stylist and perhaps s/he’s somewhere out there waiting to contact me, but I’m not holding my breath.

At the end of the day, your personal style is just that: personal. And while someone can help you along the way, if the process makes you feel bad the problem lies with the process.


PS I didn’t pay the second stylist the full shopping amount of $275. And while I won’t leave a bad review or name her here because she’s a solo entrepreneur and I respect the hustle, Dude- you gotta have some common sense! If your client is in a vulnerable state (half dressed) and you can see she’s holding back tears because of your shitty service, it’s probably a good idea to rethink your strategy.

PPS I’m trying a new thing of being brutally honest because I don’t think experiences like these get shared very frequently, so if you have feedback, please let me know!