27 Dresses, But All for the Same Wedding

I'm in a wedding this weekend for one of my very best friends. As one of three bridesmaids (plus a bridesman), I was asked to find a navy blue, cocktail-length dress so that the wedding party gives off a Destiny's Child vibe - coordinated but not quite matching (my analogy, not the bride's).

I was so excited to choose my own dress. Something that fits! Something that's flattering! Something I'll wear again! I set to work searching for my perfect bridesmaid dress.

Bridesmaid dresses can cost, like, $300, & I didn't want to go that route if I didn't have to. Instead, I started at all the standard mid-level places prone to decent dresses: Kohl's, LOFT, GAP, J. Crew, Dress Barn (stop laughing). I tried the standard Internet places: Modcloth, Shabby Apple, eShakti, ASOS. And I stepped it up a notch to department stores: Macy's, Nordstrom, Dillard's.

Alas, it seems navy blue is not one of 2015's hot colors. In fact, based on most of this year's dress inventory, you'd never know that the color navy blue exists at all. Of what I could find, certainly nothing screamed "This is perfect for a wedding!"

So I searched & searched, & I bought some backup dresses in case I got desperate. At a GAP outlet in Brooklyn, I scored an A-line dress with subtle stripes in shades of navy, probably too casual for a wedding. At the Kohl's in my hometown, I spent $20 on a chiffon-imitation polyester dress, probably a bit too short for a grown woman. At a J. Crew in Chattanooga, TN, I bought a scalloped shift in some ungodly heavy fabric, probably not matchy enough with the other bridesmaids. And from Modcloth, I found my best option: the Windy City dress, which was slightly too big but otherwise practically perfect in every way.

Exactly one week & $85+tax later, the tailored dress... does not fit. Or, rather, it fits, but it looks terrible. The tailor seems not to have taken into consideration my, uh, ample bust, thus altering the dress in such a way that the delicate pleats stretch nearly flat across my chest - but not flat enough to look, you know, good. The dress sags & bags in strange spots, giving the general feel of a plus-size woman who has no idea how to dress for her body - not exactly the image I want to project as I fly solo at my best friend's wedding.

I told the tailor, but I didn't do a very good job of it. When she rang me up, she said, "Everything is fine?" & I said, "The dress is too small," & suddenly she looked at me like she didn't speak English, & I got flustered &... paid her $85+tax & took my ill-fitting dress home.

So now, I've purchased three more. I cried on the phone to a J. Crew bridal specialist named Shekinah, who was equal parts stylist & therapist (the dress didn't fit, so I sent it back). I spent $10 on a LOFT dress from Poshmark that fits well but has the overall vibe of a blue barlap sack. And over the weekend, I bought a dress from a Macy's that fits like a dream (& makes me look skinny!) but that might not look right with the other bridesmaids.

All this to say that at this point, I have purchased 10 navy blue dresses, six of which I still own (& five of which I cannot return). All of them are fine, but none of them is quite right. I plan to take all of them with my to Philadelphia & make a last-minute decision based on which option makes me want to cry the least. When all is said & done, I had better A) end up looking damn good at this wedding, & B) thank my lucky stars that I look pretty decent in navy.