I Let A Plus Size Stylist Curate My Entire Wardrobe

I have a confession: My mother picks my clothes. Or, well, she did — until I moved to Canada in January 2016, separating myself from the only person in my life who would give me a nudge every six months or so and go, "Hey, don't you think it's time for some new clothes?"

I've had a complicated relationship with clothes-shopping ever since I officially moved up to the plus size section and had to start buying bras and jackets from brands like Lane Bryant. To teenage me, being told that the clothes in the "normal" section weren't big enough for me, no matter their "3X" label, seemed like the ultimate brand of shame. I was officially a plus size person. There was, I thought, no point to buying nice, new clothes.

But after writing about my experience trying out-of-my-comfort-zone swimwear and posting bodyshots of myself for the world to see, I figured it was time to take another step toward embracing my body the way it is. So, when Ashby Vose, a personal stylist with plus size styling company Dia&Co, contacted me, we cooked up a plan for her to send me five days' worth of outfits, with some styled to fit my comfort zone, and others meant to push me way outside my usual ill-fitting-pants-and-a-top-I've-had-for-five-years uniform.

As I waited for the clothes to arrive, I nervously emptied my closet, piling my too-big Walmart jeans and my dozen or so stretched-out tops into a bag. I was not yet sure I was ready to throw them out and treat my plus size self to an entirely new wardrobe.

But by the second day, I already knew those old clothes would never go back into my closet.

Day One: My Ideal Outfit

During our half-hour consultation, Ashby asked me what my perfect outfit was. "That's easy," I said. "Jeans, a leather jacket, and a cool shirt."

Day One of my Dia outfits was perfectly tailored to my taste — the jacket is vegan leather and is butter-soft, the shirt is reversible (the other side is a sapphire blue), and the jeans, though they were a little big on me for skinnies, definitely upped the cool factor.

Wearing this out to dinner, I expected to feel like my usual self. After all, this isn't far off my everyday uniform. But I felt different — and I knew why. The realization was good for me, but maybe bad for my wallet. Everything in my Dia box was affordable, though out of my usual price range. I'm the kind of person who thinks $20 is too much for an item of clothing. In the clothes Ashby picked for me, however, I saw the value of actually spending money on well-made, versatile, and long-lasting pieces. Nothing ripped. Everything fit. My jeans weren't baggy. The top wasn't stretched out. Each piece of this outfit can be worn in dozens of combinations with other items. When I mentioned my revelation to my wife, they said, "Good. You never spend money on yourself."

What I learned: There's a big difference between secondhand discount store clothes and new clothes. Sometimes I need to treat myself to something that makes me look and feel good.

Day Two: Playful Picks

OK, first of all: I'm going to live in these skinny jeans for the rest of my life. In her instructions for me, Ashby specifically mentioned these were supposed to replace my Walmart jeans, and they did. Pulling these on was the moment I knew I had to throw out my old clothes. I had been living for so long in clothes that didn't fit that putting on clothes that did actually felt like a physical shock.

Ashby paired the jeans with a long tunic and a jacket I would never have picked off the rack, but which feels incredible, and fits my shoulders, unlike most made-for-women jackets I try. The tunic, I was worried about — I tend to like shirts that cling to me in front, because as a teen I was always pressured into shirts that hung off my now H-cup boobs and made me look like a box. But this tunic moves as I move, and is cut close to my sides, showing off my waist. Also, it feels like I'm wearing a superhero cape.

Overall, I was comfortable in this outfit. But I was beginning to think the easy first two days were meant to lull me into a false sense of security.

Turns out, I was right.

What I learned: I was in dire need of a nice bra to go along with my new clothes. Seriously, I was wearing a bra that had zero underwires because they'd both popped out. Not the best for showing off a tight new jacket.

Day Three: Let's Get Down To Business

That's the sound of screeching tires in the distance. Not only did I pull this outfit out of the box and immediately know I was going to struggle with it, but in the interest of pushing myself, I'd decided ahead of time to do a shoot in public that day.

I'm transgender, and identify as masculine and nonbinary, but when I was describing my ideal new wardrobe to Ashby, I took the plunge and mentioned that I wanted to figure out how to love dresses and skirts. The truth was, I'd always wanted to wear them. As a teen, I felt like they made me "too girly" for my tomboy image. By the time adult me was obnoxiously dedicated to not assigning items of clothing a gender, and was willing to give them another shot, I could never find any that fit my shape.

Ashby definitely found a skirt that fits my shape. I love the look of this faux-leather pencil, and it fits me, and I can wear it pretty much anywhere.

It also makes me massively uncomfortable. During my shoot, the movement of my legs was restricted, I was ultra-aware of where the hem was sitting, and I kept tucking and untucking the top, trying desperately to avoid feeling like I was back in my Catholic high school, getting yelled at for untucking my itchy blouse. And on top of that, at my wife's suggestion, I was standing on a picnic table in a crowded park to expand my comfort zone.

In the end, I don't know that I'll wear this skirt again — not for now, at least. But I'm glad I made myself wear it, and it's staying in my closet.

What I learned: I should've sucked it up and tucked in my shirt for this photo.

Day Four: Easy & Breezy

I thought Day Two was going to be my favorite outfit, but I was so wrong. I actually cheated on this one a little, because I put this dress on the second I unwrapped it. To my amazement, it fit me everywhere. And it has a completely rad asymmetrical hemline that looks incredible on my legs. So, I knew when Day Four came around, I was going to be stoked to wear this baby out to dinner, along with the waist-hugging vest and the gold cuff.

I felt guilty, both about the cheating and about being utterly comfortable in every bit of this ensemble, so for my outfit of the day photo, I decided to steal a pair of my spouse's heels, and I purposefully chose a pose that showed off my double chin and the flab on my arms.

It wasn't until I was choosing a photo of this outfit to post to my Instagram that I realized this outfit, unchallenging as it was to my personal style, still had a lot to teach me.

What I learned: This dress is designed for plus size people. It has a big, smackin' plus size label — and that is not a badge of shame. It's an indication that this perfect dress was made for me, and for other people my size. For a plus size writer, I still have a lot of stigma about my own body, and this dress makes me feel just as good as posting my swimsuit bodyshots did.

Day Five: From Work To Flirt

And so I reached the end of my work week, and found myself coming full circle, back to clothes my mother would pick for me. A sweet dress that bow-ties in the back and can go from the dayjob to a Friday night out, a professional and cozy faux suede jacket (with pockets!!!) — even a gold-and-turquiose necklace that suits her taste perfectly.

As a teen, I blamed my mom when she took me aside and told me things wouldn't fit me. Every time we went shopping, she took a look at my armful of stuff and said, "Those aren't big enough." I thought she was scolding me — but now, looking back, I can see she just didn't want me to be disappointed. She wanted me to find things that fit me, made by people who don't just slap a 3X label on their clothes, but actually take into account the differences in plus size folks' bodies.

As a fashion and beauty writer who often writes about fat positivity, I know lots of brands who design for plus size folks. But somehow, despite knowing how genuine they are, despite seeing their clothes on other plus size people, I still assumed those clothes weren't for me.

I still assumed I would take an armful of them only to be told I wasn't right for them. I still assumed I didn't deserve clothes that made me feel good. I still thought I shouldn't bother giving my body and myself nice things.

What I learned from this entire experiment: I was wrong, and plus size fashion risks are always worth taking.

Note: Dia&Co currently ships boxes to the U.S. only.