Finding My Style – The History

I’ll admit, I’m wardrobe challenged. Obviously I have clothes. I’m just not what many would consider fashionable. Bryan actually told me a few weeks back that his mother dresses more fashionably than I do. His mother is in her late 70’s. Seriously?!? 

It isn’t that I want to be a trend setter, or anything like that. But I would like to look a little more polished and put together. Part of the problem stems from how I was raised. We were Catholic School kids, which means from Kindergarten to Senior year I was donning a uniform. My Mom wasn’t big on spending a lot of money on clothes, so a lot of what we wore were hand-me-downs and clearance finds. Once we were teenagers, we were given enough money to buy an outfit before the school year began, and then had Birthday and Christmas money that we could spend on clothes. My birthday is in November, so most of my annual clothing money came as winter was approaching. I’ll admit, it always stressed me out: Buy more fashionable (uniform) clothes to wear to school? Jeans and things for the weekend/after school? What about summer clothes?

I had a job from the time I was 13, and all my teenage jobs required a specific outfit. The college I went to was very small, and very relaxed, so I usually bummed around campus in T-shirts, sweats, etc. And my first job out of college? In a restaurant, where I had to wear “black and whites”. I went out into the real world with no sense of personal style, and no idea how to put together a wardrobe!

Adding to the issue is the fact that my weight has been all over the place. In the 14 years I’ve been out of college, I’ve been every size from a 4 to a 16. Twice. When I’m bigger I hate buying any clothes because “I’m not going to stay this size”. When I’m smaller, I have a hard time finding things that fit my frame; I’m short (5’2), and have curves even when I’m “too thin”. I tend to buy clothes for an occasion: There’s an important meeting at work, and I need to look presentable, so I buy a new outfit. Or, we’re having a party, so I buy an outfit. And then I work those pieces into my everyday wardrobe.

It’s always bothered me that I didn’t have a better selection of clothing. But, being part of a couple, I now get to hear about how much it bothers Bryan as well. He likes that I’m a casual/comfortable kind of girl. He just wishes I had a bit more variety and style to my wardrobe.

Over the last year, I’ve been scouring the internet for ways to build a wardrobe. How do you create a closet of clothes that actually look good, without spending a fortune? I’ve read a lot of excellent advice, like creating a “personal uniform”. That resulted in me having 5 of the exact same sweaters, in different colors. Not exactly what I was hoping to accomplish. My sisters subscribe to the “Buy everything and anything at Goodwill/on clearance, so you have tons of options” philosophy. This doesn’t work for me because A) Thrift/Clearance shopping overwhelms me. Too many choices, too much chaos. My mind immediately shuts down, and I start to feel claustrophobic. B) Then you just spend a bundle (a couple of bucks at a time) on clothes you’ll probably never wear. And have a closet full of chaos.

I’m never sure what to buy. I buy things, and then I don’t know how to work them in to my wardrobe. I end up with clothes that are uncomfortable, or don’t fit right, or that I just don’t feel like are “me”.

What’s a clothing challenged girl to do?

– Cindy W.

Coming Soon: A possible solution?


  1. I also have had a lot of trouble with this, and also chalk it up partly to the Catholic school thing! I didn’t go to a uniform-wearing high school but it still took me years 🙂 Plus I gained a lot of weight in high school and was trying to hide my body. I’ve bounced around in a smaller range (8-14) but that also didn’t help. I still would not say I’m “stylish” but I did at least figure out a couple of shapes that work well for me and try to stick to “scanning” for them when I shop. Looking forward to reading about your possible solution!

    1. Yeah, I’m definitely not looking to become a style icon or anything. But my style has drifted a little too much into “frumpy” territory lately. Mostly out of laziness. And I’m really not very fond of shopping for clothes.

      I’m at least starting to identify some brands that fit my shape. That helps a lot!

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