I Had a Stylist I Never Met Pick Out Clothes For Me; Here's What I Learned

POPSUGAR Photography | Samantha Sutton
POPSUGAR Photography | Samantha Sutton
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I'm picky. My mom hates buying me clothes (I always return them), and I'm horrible at receiving gifts; basically I don't trust other people when it comes to my style. But I'm also short on time to actually go shopping. So when I got an offer to try out a clothing delivery service, I decided to fight my aversion and give it a try.

The company I would be working with is Trunk Club, an online personal styling service that while once was only for men has now added women's clothing to its straight-to-your-door delivery. I was connected with my stylist, Chelsea Brown, and we hopped on a quick call. Yes, I was skeptical. "How could someone know what I like in just 10 minutes?" I wondered.

Chelsea got down to business, asking about my sizing, brands I like, and if I was shopping for anything in particular. This time around I focused on the basics: jeans and work-appropriate tops, along with a few party looks for the holidays. After we wrapped up, Chelsea emailed me a preview of what would be coming my way: 15 pieces all hand-selected to fit my personal style. Then, the wait began . . . and ended almost immediately (the package arrived within a few days).

Opening the box felt a little bit like Christmas came early: inside was a collection of goodies for me to choose from, only while gifts happen to cost the receiver nothing at all, whatever I picked would go on my credit card bill (terrifying, I know). As I pulled out each piece, I was genuinely surprised and pleased to find that everything was pretty much up my alley. Chelsea clearly had a great idea of what I was into . . . win! Along with the box was also a list of the pieces and their prices, which leads me to my one and only hang-up: the cost.

Prices ranged from $38 for a turtleneck tank all the way up to $498 for a DVF dress. Most items fell in the $150-$350 range, which for some may be totally workable, but for me proved a bit pricey. I could definitely afford to pick and choose an item or two, but with the whole box totaling $3,700, I would be giving up a few months' rent for all the items – not really an option. I know that other styling services like Stitch Fix offer affordable alternatives, but Trunk Club's request-as-you-need-it model (as opposed to other services' monthly subscriptions) matched what I was looking for. Also, I'll admit it, I have expensive taste, so I would rather pick one nice thing for myself anyways.

Just scroll for a look at what arrived at my doorstep, along with a few major takeaways to consider before trying something similar yourself.

Here, the jeans fit perfectly, and I loved the jacket (Chelsea mentioned that she sized up because of how it was running, and it was the right move). The tee was comfy and simple – I'm a big fan of T by Alexander Wang, and the boots fit well too.

Wearing:

An LBD is my go-to for holiday parties, and while this fit-and-flare style was snug, it was probably a little more feminine than I would go for. Also, please excuse my sneakers (they were what I wore to work that day and totally don't match).

This long vest was one of the pieces I was most looking forward to trying. It's structured and sleek, and I love the side slits that allow movement without being too flowy. The top is a solid layering piece and seriously soft. I had mentioned to Chelsea over the phone that 3x1 was one of my go-to denim brands so I was excited to rock a pair. The flares fit well, but I felt like they skewed a little older once I actually put them on.

Wearing:

This shirt had so much potential: a casual white button-down that was just the right amount of sheer. Sadly, maybe due to my mishandling or maybe just the nature of the fabric, it was totally wrinkly. I felt a little too unprofessional in this one.

Wearing:

This shirt/sweater combo was probably one of my favorite items in the box. Some may write off a fake layering piece as silly, but I was really into it. I felt like a styling genius without having done anything. The jeans were a tight squeeze (barely zipped them up!) but I did finally manage to get them on, only to find they were also a tad long. As someone who is 5'9" it's not often I have to hem jeans, but these were made for someone with model proportions.

Wearing:

When it comes to party dressing, this look was definitely the most puchy of the bunch. The colorful bell skirt was girlier than I would usually opt for, but it felt festive and fun. I probably could have sized down in this one, but I still thought it was a flattering option for any upcoming holiday celebrations.

Wearing:

This turtleneck top felt like the perfect mix of cozy and sophisticated. It was soft, yes, but the cut felt modern and it was actually pretty flattering, which can be tough with any sweater-ish material. I paired it with the flared jeans for a more dressed-up look.

Wearing:

This dress left me feeling a little like Goldilocks. It was too tight to wear to work but felt a little too formal for a night on the town. Maybe it was meant specifically for office parties? Anyways, it was a little too formfitting for me to be totally comfortable wearing it in public.

Wearing:



Takeaways:

The experience was overall a positive, but there are a few things I've learned, lessons that will come in handy for anyone considering Trunk Club or a similar service.

  1. It's highly unlikely that you'll keep everything. I went in to the experience planning to hold on to the entire box, but in reality it was a pick and choose situation.
  2. Letting a stranger shop for you is less scary than you believe. Chelsea easily chose pieces I could incorporate into my wardrobe and mix and match with what I already own.
  3. This service was truly painless; a box appeared at my door and I had 10 days to decide what to keep or return. There were no dusty dressing rooms, long lines, or cleared-out shelves to sort through. And if something wasn't the right fit, there was no hassle to return it, it simply went back in the box and was on its way.
  4. Trying a service like this may actually introduce you to something you wouldn't normally wear. A few pieces – like the dresses — were items I wouldn't have picked out myself, but they ended up winning me over!