I loved Angie's soft masculine summer outfit on her:
I did not think this would look good on me because my style tends to be very ladylike and I don't do well with tomboy or masculine looks. But I had similar pieces in my closet so I thought I'd give it a try. Plus right now I'm doing forced exploration of my closet to try to assess my older/lesser worn pieces. These blue button down shirts are all old. I don't think light blue is my color so these may have to go. What do you think--purge all of these shirts or is one of them worth saving?

As an apple, I felt rather self-conscious about tucking and belting the shirt, but gave it a try anyways. This outfit does technically meet my rubric criteria (Color--raspberry, Pattern--animal print and striped shirt, Matchy-matchy--animal print belt and shoes and red trimmed shoes matching raspberry blazer, Fitted--shirt tucked and belted, Flair--leopard pumps), but I admit it's a little out of my style comfort zone. What do you think--is this ladylike enough with the heels to fit with my style or should I give up on trying masculine looks?

1. My attempt to copy Angie (in #2):
Old Navy striped shirt
Kut from the Kloth white skinny jeans
Tulle raspberry blazer
Animal print belt
B Makowsky Heist animal print pumps
Jason Wu for Target cream and navy straw bag

And keep or toss on the light blue shirts:
3-4. Old Navy striped button down
I like how it's more fitted than the second blouse, but I think it may be too short. I don't remember buying this but I think this may be my brother's shirt that he left behind at my house many years ago.
5-6. Casual Corner striped button down
DH used to compliment me every time I wore this shirt. He likes seeing me in classic pieces like this shirt, or red turtleneck sweater with jeans, etc. This is also ancient (I mean it's Casual Corner, LOL!) It looks like a better length than the first one. But is it too baggy for my figure?
7-8. Ann Taylor satin button down. It's slightly shiny. This was my interview shirt that I wore under a black Ann Taylor suit for all my residency interviews so it's about 15 years old. I now realize that I don't look good at all in this shade of powder blue.

So the question is, should I try to upgrade to a nicer blue pinstripe button down shirt (like Anne Fontaine!) someday, or should I give up on this style of shirt altogether?

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