So, here's the thing:

As of May, it will be the 33rd anniversary of me dressing in whatever sorta, kinda fits, and never once actually dressing in clothes and makeup that make me feel great, comfortable, pretty, or sexy. My style is "getting by and out the door before I get too depressed to not go out at all because of my looks."

I'm done. So, so done with it.

I deserve to feel good and look good. It's high time I admit that I actually really, really like fashion and makeup and shoes and want to dress really well, but have spent my entire life too depressed with such little self esteem that I wrongly believed that I would never look good and didn't deserve to ever feel confident about my physical appearance.

But here's my problem:

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I don't understand how to put together a stylish outfit or what kind of makeup would work for me, what my body type actually is, what kind of shapes or looks would be flattering for me, or basically...anything having to do with fashion or being pretty.

I'm trying to put aside about $1000 by my birthday (yes, really) to completely change my entire wardrobe and make myself over. I am a big fan of classic, tailored styles, and I think it would be cool to wear more skirts and dresses (but I really adore my jeans, trousers, button down shirts, men's clothing tailored for women, and blazers).

I'm willing to spend more money on pieces that are timeless and really well made, but my personality is a bit more funky and eclectic and much more vintage/thrift store inspired.

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Ideally, someone (or someones) are willing to literally - in meat space - go on this adventure with me around Memorial Day-ish, but in the meantime: TEACH ME, O WISE FASHION AND MAKEUP MAVENS OF GROUPTHINK!