Fashion Advice

I have been watching What Not To Wear on Netflix of late, which always makes me analyze my wardrobe to death and feel I am wanting in one particular area. I need dresses, or skirts. At least one nice skirt and one fun one, and at least one fun dress to match my more formal black one.

In short: I have one dress and one skirt that fit me, and I feel like Stacy and Clinton would run me out of town, throwing shoes with 4" heels at me as I fled.

About once a year, I look at dresses online, try a few on in different stores, and come to the conclusion that 1. I am a giant and 2. I need to learn to sew.

Here are the reasons for my problem:

I'm 5'9" (actually a little taller), and I am long-waisted. I also have broad shoulders, kind of like a linebacker, but not so much. This makes dress-buying hard, because I'm often limited to sleeveless dresses. Also I am limited to no dresses, because the waist on nearly every dress I try on is positioned roughly between my actual waist and my chest region.* It would be great if that meant I just automatically got empire-waisted dresses...except that lack of body length usually puts the hem at my upper thigh or higher, and I am not selling anything. I want to keep my dresses appropriate, so I don't feel self conscious.

Skirts work, sometimes, because they don't depend on my midsection being a certain length. That being said, I find old-lady skirts, short SHORT skirts, and skirts that are ridiculously expensive (and boring) when I go shopping. This year I found one at Target, a belted circle skirt in a fun print, but that is all. In the dress department, I have one little black dress I found at T.J. Maxx that is long enough that I think people won't imagine I'm open for business if I wear it out and about. But it is a black dress, and it does look dressier than what I'd want for every day.

Isn't it sad that I have to keep worrying that people will mistakenly think I'm a hooker when I try on dresses? Tall people have to deal with that sort of thing.

All that being said, I really don't hate my shape. I like being tall-ish, and I like my shoulders. They aren't obviously lumberjack-like, and they do hold up my clothes nicely. I know the issue isn't me, it's what is available in stores, and that's what I find so frustrating. I could go to a tall girl store, but those places are PRICEY and far away. If I order online, I have to send packages back and forth like boomerangs, and that's always annoying and usually expensive, especially if the shop doesn't give free return shipping.

I've mostly given up. But then I saw this post from In The Fun Lane and I fell in love with the shirtdress, which is from Old Navy. I want it. I think it would be cute, and it looks long enough. No shaping means that it won't cause the same waist positioning issues I usually run into. And it's supposed to be built looser, so maybe it will fit my shoulders.

I'm picturing it with leggings or tights, my new Christmas boots, and a handknit scarf.

The question is this: Should I take the plunge? Should I order it, and potentially be disappointed when I discover that dresses aren't built for me? More importantly, am I too tall to wear the tunic/legging look? I don't want to look like I'm pretending to be 5 years old.

Advice would be appreciated. And yes, this was an entire post asking for fashion advice. I regret nothing.

* The proper seamstress-y term is bustline.