Pick 5 Fashion Challenge recap

As March draws to a close, so too does the Pick 5 fashion challenge my friend and I came up with a few weeks ago. In this challenge, each of us picked five items and pledged to wear them every week until the end of the month.

And you know what? I'm SO GLAD it's over.

Here's what I learned from doing this challenge: There are some very good reasons I don't wear these things very often (except for the pants, that's mostly just laziness). And I think spending some serious time trying to think about how to style them has given me the freedom I needed to just ... let them go. But anyway: Here's how it all went down.

Pink oxford shirt

I have incorporated this shirt into previous fashion challenges, and it has really confounded me as to why it is so tough to wear. But I think it's the color. There is something about this particular shade of pink that just doesn't get along with the rest of my wardrobe. It's been hard to get rid of, partially because it was a gift from my husband, but I think it may be time to say goodbye. Or to dye it raspberry ...

Gray booties

I have a genuine love-hate relationship with these booties. Every time I wear them, I get compliments, and I definitely don't regret buying them. But they are never going to be a staple wardrobe item for me. And maybe that's OK. I hereby give myself permission to only wear these five times a year and not feel guilty about it.

Polka dot trousers

I kind of failed at this challenge, because I basically wore these with the same color scheme both times. Oops. What can I say, I like pink, mint and tan together. But, honestly, I would like to push myself to wear these in some more creative ways.

Cobalt cardigan

This was the challenge item I was dreading the most (I literally had not worn this sweater one single time since I bought it over a year ago — shame!) but it wound up being easier to style than some of the others. What that tells me is that I should look for a similar sweater in a more flattering cut (this one is way too boxy for me). That being said: I will probably hang onto it until I find a replacement for it, because now I suddenly want to wear cobalt with everything.

Khaki shirt dress

Total fail. I tried, believe me, I TRIED to come up with something other than red to wear with this dress. And I just couldn't. By the end of the two weeks, I was feeling super grouchy about this dress (which I loved when I bought it) and I kind of wanted to set it on fire. The truth is, I find khaki hard to wear. It just seems to dull things down for me in a way that I don't like. So I am planning to sell this dress. I do still love it, in a way — but it's obvious that I don't love wearing it! Which is odd, when you think about it.

I also learned that I have no desire whatsoever to attempt a capsule wardrobe again any time soon! I really admire people who do this, and I understand the point of it and the benefits of it. But it's just not my style. So instead, I'm checking out some fashion challenges for April — you can follow along via Instagram (I'm @breadandrosesvintage).


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