Dear Daddy Likey: I can't find a damn dress!

I received these two reader questions via email at around the same time:

Dear Daddy Likey,

I'm 18 years old and going to a benefit for an organization that helps emerging young playwrights, and I can't find a dress online that I like, or that fits my needs. I haven't worn anything shorter then a three quarter length sleeve since a few summer's ago, and so I need a night-time dress that would also work with a cardigan/long sleeved top and tights. You probably would rather do something much more exciting then give me ideas, but since we have a similar style and body shape and you are a hilarious genius, I figured you would be the girl to help me out. Oh, and I'd need it to be fairly cheap. Girls got needs.

Signed,
Short-Sleeved Shakespeare

and

Dear Daddy Likey,

I’m in a bit of a dilemma. I’m being forced to go to my high school’s winterfest dance, and I haven’t any idea in the slightest as to what to wear. I went to homecoming in a fringed pale pink dress by H & M, and, as much as I loved it, it was hardly figure-flattering, and not exactly a proper dress for the occasion. Winterfest is generally just a colder version of Homecoming or Prom (instead of the customary football game no one goes to with Homecoming, there's a basketball game no one goes to). I'm thinking I have a rectangular figure, but perhaps it's a cone...I can't really tell...Could you give me a few tips?

Signed,
Rectangle, or Perhaps Cone

Dear Shakespeare and Cone,

I thought I could group these two queries together because both of you are adorable teenage readers in need of formal dresses, and since one of you has a similar body shape as me, and my body shape could also be described as a rectangle, or perhaps a cone, I think this pairing will work out swimmingly!

I was actually out shopping today, and tried on a few dresses, and let me tell you: I hate shopping for dresses. I've realized that my problem is that since I'm so thick in the middle, wearing one piece of fabric makes me look like this rectangular mass, instead of a perfectly normal non-mass with legs, waist, and chest. I'm not sure if you guys are experiencing the same issue or if I'm the only mass around these parts, but here are some ideas for you, regardless:

Something like this would be so great for an emerging playwrights benefit--doesn't the model look just like a young tortured writer? This is something I would have worn when I myself was an 18-year-old tortured writer, so I can vouch for its authenticity. Other bonuses: it has sleeves, but the lace keeps them delicate instead of bulky, it obviously looks fabulous with tights, and you could totally wear it again with a slouchy cardigan and some flats.
Velvet Torch Lace Party Mini Dress, $54, nordstrom.com

I think this dress (or something like it) would be fantastic for both occasions:

The color is a stand-out, and the ruching across the waist is super flattering. It would work on its own or with a cardigan and tights, and can you believe it's from Sears??
Trixxi Ruched Glitter Dress, $79.99, here. If that price is a bit steep (seriously, WTF, Sears?), look for similar styles on ebay or at stores like Marshalls and TJ Maxx.

Completely Gratuitous Sidenote: I can't mention Sears without telling you about the time I was at a group job interview with a girl who used to work at Sears, and the interviewer asked us all to give an example of a time where we had a problem with a coworker and how we solved it. This girl told a story about how one of her coworkers was in a really bad relationship so she offered to let the coworker move into her apartment, on the condition that she stop seeing her asshole boyfriend, so the coworker moved in and they became best friends, but then she found out that the coworker was actually still doin' the nasty with the asshole boyfriend, so they got in a big fight and the Sears girl was like, "You can just HAVE my apartment, cuz I don't want it anymore, bitch!" and moved in with her mom, and this story went on for like fifteen minutes as the rest of the applicants and the interviewer grimaced and laughed nervously and sank lower and lower into our chairs. Finally, the interviewer interrupted the Sears girl and asked, "Wait, so how did you solve this problem?" and the girl was like, "I didn't. I hate her and she stole my apartment. That's why I'm applying here."

Moving on...

LOVE this:

And not just because it's my favorite color.
London Times Satin Pleated Tie-Back Dress, $50, overstock.com

Another great option for formal occasions when finding a dress proves hellish: try separates. Just find a dreamy, dramatic skirt, like this one (which just sold for $20 on ebay!)...

(JC Penney also has a gorgeous purple one on sale for $50, here)

...And pair it with whatever feels comfortable and appropriate for the event. My young playwright might add a basic black sweater set and look absolutely dashing, while the lovely Winterfest attendee could try a sequined sleeveless top. The possibilities are endless, and dressing in separates can be easier and more flattering than scouring the earth for the perfect dress. I wore a poofy pink skirt and ruched brown tank top to my senior prom, and even though I eventually turned into a drink menu, it was a great outfit while it lasted.

Best of luck to you, and I hope you ladies have a lovely time at your prospective events!