(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.

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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.

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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:

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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.

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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.

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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.)

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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.

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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?

23 comments on “(I’m Almost 31), and I Still Can’t Dress Myself

  1. Shannon

    My office is (unsurprisingly) very corporate. I typically wear a dress and heels every day—usually black. I’m boring. (But they all look different, I swear!)

    I gravitate toward structured sheath dresses. No cap sleeves, ever. Preferably slightly above knee-length so I don’t look stumpy.

    On the weekends, I do jeans and drapey T-shirts with boots or Chuck Taylors or ballet flats. Or a more casual dress.

    Once you find a look you like, fits/flatters you and you’re comfortable in, just keep replicating it.

    1. Shannon

      @Shannon: Oh, and to be lame and reply to myself—meant to add that since I wear dresses in the same 4 or so styles, I like when pieces have interesting details. I have a T-shirt style dress that has leather sleeves and a leather collar—just enough to make it pop a bit more. Or a little lace detail or something…

  2. Mom

    Ok, where do I find all these box people I’ll start Christmas Shopping tomorrow! I’m still looking for my style!

    Love your Mother

  3. Janine

    I have been doing stitch fix for a few months now. I actually have been less satisfied as time has gone on. I was mostly happy with my first couple, but out of the last two “fixes” I have only kept one item. I love the concept, but I am not sure how much longer I will keep doing it. I hope you are more successful!

  4. Kim

    I am so not a fashionable person! If I could, I would wear running clothes all day, every day. I just accepted a job that has a casual attire policy and I’m kind of excited about not wearing clothes that I’ve had to wear up to this point, but I do need to step it up from my “can-I-just-wear-my-Nike-tempo-shorts?” attitude. I’ll look into giving stitch fix a try!

  5. Kelsi

    I have loved my stitch fix boxes. I’m pretty sure the last two fixes I’ve kept almost everything. I do think that it does get better over time. Kind of in the same boat with fluctuating weight and there have been things that have fit to a T. It’s awesome.

  6. Caitlin

    Firstly I love that comment from your mom! “Those box people” hahaha.
    Secondly I did not know that Stitchfix is supposed to get better with time (I guess that makes sense…more data means they can better hone in on what you’d like) but I really wasn’t into my first box. Either I didn’t like what i was sent or the stuff I did like was too expensive, even with the $20 credit. I do love that sweater that you loved though! I’m not surprised you didn’t like that first dress. It’s very 70’s fondue party lounge.
    Thanks for such an honest review! I still don’t really want to give Stitchfix another shot but I love reading what people got.

  7. Melissa (fitnessnyc)

    I consider you INCREDIBLY fashionable, so maybe I need stichfix. You always look so put together, whereas, I spend at least 3 minutes each morning wondering whether I can get away with wearing yoga pants to work.

  8. Kristen

    I figure that picking one item a box is fine and I consider it a win. Even if I just pick one thing, I still get style ideas from the items they send and I am not losing money. If I bought everything that came in the box, that would mean essentially all new clothes come from stitch fix, which I don’t want, either.
    I did get that tulip sleeve top in Navy and I kept it.

    I’ve had four fixes — I kept 3 items, then 2, then 1, then 3 (but I would have kept the whole box, but I had recently bought similar colored jeans).

  9. Gwen D

    I’m all about simplicity/versatility. I do a lot of travelling and live out of a suitcase so there’s not that much I can take. It definitely makes everything a tad simpler.

  10. Katie @ Talk Less, Say More

    I don’t really know how to dress myself but I do feel like I’m better than I used to be, but I have to admit that working from home makes me want to wear leggings everyday and find the best options for tops or sweaters so that way I can wear them everyday without looking like a slob if I have to run out or take a video call with my boss. I’ve heard good things about Stitchfix but haven’t actually tried it, maybe one of these days.

  11. Jody Billings

    I find the worst thing is that my husband is such a slob, it tends to rub-off after twenty years. The man doesn’t care what he looks like and it’s an uphill battle not turning into a female version of him – especially around the house.

  12. JennyJones

    The fewer the pockets, the bigger my handbag! And who wants to carry around a tombstone bag that weighs a ton and looks like we’ve been shopping?! Ironically, it’s the busiest of us with corporate jobs who make the most time to look decent!


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