Love you in #1!

Thanks for the feedback, everyone! I was in a pretty silly mood when I wrote this but I'm glad the analysis paralysis resonated with some of you. I do have a relatively serious anxiety disorder that has been a lifelong struggle. But to some extent it's also my strength -- a lot of the same analysis traits are useful in my career. At any rate, sticking to all black really does make my life easier, but I've always preferred guidelines to rules, and it's fun to try new things.

I agree with the suggestion that I should try a few other pinks. Watch this space for more photos!

I do like the Madewell shirt. I wore a lot of pastel oxford shirts to school as a kid (my mother often wore them too). I'll keep an eye out for something paler but in the same vein.

As for the sneakers, it's a frivolous purchase so I'm looking to keep the cost low, thus the focus on Converse. I might order a few options.

And the dress... I own far more than I wear, and I'm trying to be smarter about that. I have a vaguely similar McQueen sun dress that's a total closet orphan. But for $30, it's impossible to pass up, so I think I'll stop back by Crossroads today or tomorrow and snap it up. It looks more "me" in the photos than it did in person, somehow, and my partner loves it.

What Angie said. Buy the dress in 3 if you still can. Love the color in 2 on you.
Pink is a loaded color...shy and bashful or blatant look-at-me bright neon; innocent and saintly like pearlized pales or sexy and bad fleshy tones; feminine or masculine (as it was originally); seen in both sunrises and sunsets. How about dusty, earthy pink sneakers or oxfords, maybe suede and studded? Dark soles and laces? Distressed pink tee or one printed with a dark quotation?

I meant to say that you could tell your brain that you are doing science...color experiments.

Approprio:

I'd probably say I'm an ENTP rather than INTP but the extroversion is very situational. I agree exactly about how it's easier to pick out cool unexpected things than to go on a hunt for a specific item. And I love those pink bombers. (I wish the Jil Sander one came in black as I've been looking for something just like that...)

LaPed:

Ha!! Of course I'm a year behind the trend... so it always goes with me. First reaction, a few years ago: ew, pink. Slowly, as I start adjusting to the new idea, I buy into it - and then it's over. But at least that means prices are discounted!

Can I just say, as a fellow redhead (very similar hair color and texture, less pink skin tones), pastel AQUA?

I hope you are able to get the dress! I did like that first top on you, it seems like a shade worth exploring some more, with your coloring.

I can relate somewhat to the tendency to 'overthink' purchases etc. Ive tried to simplify my wardrobe to remove some of the decision making by minimizing the colour palette of core items or base layers + then adding new or untried colours by adding them in the form of accessories (shoes, scarves, earrings, bags etc)
That's also why I find thrifting allows you to 'experiment' without a huge outlay + thus making any 'mistakes' small + relatively inexpensive.

The style of the first top may not thrill you, but the color is great for you. It doesn't wash you out at all, and it really does suit you well. I think the color of the second top may be a bit too bright or maybe intense and it comepetes with your face and for that reason I don't like it as much. Love the dress!