(I’m Almost 31), and I Still Can’t Dress Myself

It appears this is part 2 of a series in which I try to learn how to dress with more style.

If this is not the only blog you read (hi Mom!), then you’ve probably heard of Stitch Fix. (referral link)

It’s a subscription box, but it’s clothes, not beauty products or running products.

You start by filling out a style profile.

There were no options for: really really likes Lilly and J. Crew and must bust out of that box, so I just said I really, really like preppy clothes.

And classic. True story: when I brought a bunch of clothes to get tailored after I lost weight, I brought in an Ann Taylor jacket and dress. I was with my mom, and the tailor was really confused. “Are you sure this isn’t your mom’s?” OMG I JUST FOUND IT ON FACEBOOK.

So dowdy.

I moved to New York, lost a bunch of weight and still wasn’t quite sure what my style was. I found a Gilt deal for a stylist, and had a session with her. It was fun, and I applied some of what I learned with her…for a while.

But I gained a little bit of weight, and I find myself retreating back into dressing to hide, not accentuate.

I started a new job about a month ago, and I think I still have time to trick them into thinking I have some style before they know me too well.

I was so excited for my first box to come.

Here’s what was inside and my thoughts:

I saw this dress in the box, and immediately wrinkled my nose. The pattern is not me at all. I was tempted to not try it on, but decided to be open-minded.

It fit REALLY, REALLY well–like better than a DVF but for a fraction of the price–but I just couldn’t get into the pattern. My office is pretty casual, and I walk everywhere in NYC and am usually too lazy to carry heels, so I would probably style it the first way…but yeah, still couldn’t get into the pattern.

I LOVE THIS SWEATER. I’ve been rotating who I wear it around so I can wear it as much as possible.

It is comfy, but flattering at the same time. ALSO, IT HAS POCKETS. So far, I’ve worn solid tops under it, but I suppose I can get wild and wear stripes or something crazy.

So, I liked this top. It fit, and I liked the color. But it was $68, and I didn’t love it, so it went back. (Hey Stitch Fix guys? Can you send the skirt next time? I LOVE that.)

I loved this top to death. It was completely my style, but it was a little too small. I guess I mostly shop in places that vanity size – J. Crew, Ann Taylor/Loft, Gap – because I said I was a small in tops. I am not really a small. I went in and changed this immediately so that I can get more cute tops like this that my boobs might actually fit into.

I was very unsure about this jacket. I wanted to like it, but I just didn’t. I can’t tell you if it’s the cut or the fabric, but something about it felt a little conservative for even me

My friends tell me that the boxes keep getting better with time, so I’m going to stick with it. They charge you a $20 styling fee, but if you buy something, that’s applied as a credit, so I was able to get the best sweater of my life for $38 instead of $58.

You can sign up for an invite here (referral link) and get your own box o’clothes. I’m excited to see what comes next month! I do love shopping, but I definitely need some help stepping outside my comfort zone.

What’s your style like? Have you/would you ever do Stitch Fix? What are your favorite style blogs?