I've been growing a bit of a love affair with shift dresses. Their loose styles are so non-restricting, comfortable, and they come in so many styles from very casual to very dressed up. However, over the past few weeks it's been dawning on me that perhaps they only look nice on very thin ladies, as I am constantly wondering if they are making me look bigger than I am when I go out.

So I purchased a new dress I've been eyeing on Modcloth for awhile (pictured below except mine is gray and cream in color). I thought it's more structured shape might also be more flattering on me while still remaining comfy and pretty. I got it in last week and wore it this weekend when my fiance took me out. I paired it with white, lace up heels and a white pussy bow blouse underneath. I also straightened my hair and pulled it to the side with a small bow. I thought it look fairly cute and had hoped to take pictures to share with you all.

We went to go visit the Winchester Mystery House, and it all turned sour right around the time I wanted to take photos. I already realize I'm not very photogenic (a story for another day), but everything about this outfit looked TERRIBLE on camera. What looked sweet and put together at home now looked baggy, sloppy and silly on camera. I was so embarrassed and I wanted to wear my long coat after that to cover it all up. Afterward we had tea and strolled some shops and there my suspicions were confirmed. I look undeniably SLOPPY. I didn't think the dress was too infantile, but I felt so stupid compared to other women in tighter clothes, pants and well...normal attire.

I don't know why I feel this way as I really do not feel comfortable in those types of clothes either. But I started to feel like a little girl playing dress up. I don't know why. I don't like feeling sexy or too serious, my heels had a wingtip design and weren't cutesy mary-janes, the bow in my hair was small and discreet and my hair wasn't in big, bouncy curls. But I'm starting to feel the same way I did in the shift dresses. Perhaps I'm not thin enough to pull off this style? Maybe I don't wear enough make-up? Should I invest in shapewear, although I really detest anything tight, especially around my waist.

I'm starting to grow very discouraged. I know what I like-ultra feminine details, soft, delicate fabrics, girly silhouettes, etc. So why is it impossible for me to piece it together? I feel like searching Pinterest or Tumblr is useless because all those models are so much thinner than me and the clothes hang off their bodies in a very different way. I don't have a very cute face either, it's long rather than round and I wonder if that too adds to the problems I'm constantly running into.

Can you please share your experience about this disconnect? I know tailoring is HUGE when it comes to looking sloppy, but I honestly feel everything fit me as it should, especially as I had just finished adjusting the sleeve cuffs on the blouse which I had thought helped immensely on the fit. I suppose not.