It Doesn’t Help That I’m Fashion Challenged

So I went on this little rant deal the other day about not being able to find clothes that fit. I thought about it some more and you know what part of the problem is? I have no real idea of what looks good on me to begin with. I have no fashion sense what so ever, no sense of a personal style, although I do so love the look of the 40’s and 50’s.

Consequently, I tend to buy something that catches my eye, then I get it home and have no idea where I’m going to wear it, how I’m going to wear it, or what to wear it with.  For example, take this cute little number.

Last year's body. Not so sure how it would look on me today.
Last year’s body. Not so sure how it would look on me today.

I loved the fit when I bought it, but now that I’ve added an inch or two hither and yon, it’s got just a little bit of snugness that stops me cold in my tracks. I’d love to wear it as I think it still flatters me, but now I’m stupid self-conscious because NO ONE else in my environment wears anything that looks like or fits like this does.

Oh, and then there’s this one.

All the ruffles, lol.
All the ruffles, lol.

It’s the most girly thing I’ve ever bought. I love the fit, the colors, everything.  But again, I’m stuck because I don’t know how to wear it? Do I pair it with a belt that just serves to accentuate the belly roll or do I let it hang loose giving the impression I’m hiding a pregnancy? And what shoes do I wear?

Speaking of shoes…giphyThis is a sampling of my collection.


Each one brings me such joy (and a fair amount of foot pain, but eh…the cute ones always do) but most of them sit having never seen the world beyond my closet because I have no idea what to pair them with. Ninety percent of my wardrobe is made up of jeans and tee shirts. The places I go the most aren’t conducive to wearing heels – I don’t believe one should wear heels when one expects to do a LOT of walking on hard surfaces or where there are a lot of steps / steep inclines (i.e. grocery store, mall, concert stadiums, museums or ancient ruins)…oh, and cobblestone paved walkways (*gives the Riverfront in Savannah the side eye*).

Where is that fashion fairy godmother when I need her?


10 thoughts on “It Doesn’t Help That I’m Fashion Challenged

  1. Love this post. Love the Snow White image too, lol. Shoes. Sigh. Sadly, Riverstreet is not conducive to that wonderful collection of heels you have though I’ve seen plenty of intoxicated women manage the cobblestone just fine. You can’t go wrong with a maxi dress and some cute sandals. 🙂

  2. When (and if) you ever get back up this way, we’ll do shopping, as it’s always better in pairs–just like shoes!

      1. Ha, I grew up on those beaches, surfing and bodyboarding mainly with my grandad, but I hit college and went nearly everyday for my second year. Even went surfing in between split shifts at the restaurant I used to work at!

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