Here's a problem I haven't had in a while ... what dress to wear? (with photos)

As a person of size, my clothing choices in the past have largely been driven by the same considerations as those motivating military camouflage designers - - how to obscure and hide my shape as much as possible.  Dark colours were always my preferred go-to palette, with as many layers as possible to hide my various rolls and more abundant bits.

This year, though, I am trying to come out of my shell somewhat, and embrace a new, more confident me.  At least sometimes, situationally, when it is warranted.  I may wear black suits 5 days out of the week at work, but occasionally I get the chance to break out of that stuffy lawyer mold.  Next week is just such an occasion.

My firm is having its annual "non-denominational festive holiday party" next Friday, and, just like the cliche, I have nothing to wear.  You see, since last year's party, I have lost 75 pounds (yay!), and dropped 3 dress sizes.  Which is fine, except that the dress I wore last year, a size 26, will look like a tent on my new size 20 frame.  Not to mention the fact that the "girls" (ahem) would just fall out of that dress now - - not the lasting impression one wants to make at the firm party, I think you would agree.

Now let's not get thinking that I am skinny or anything - - at 258.9 pounds and a size 20 I am still one of the largest (if not the largest) person at my firm.  But I think that it is time to embrace my new body, and enjoy it for the shape that it is, rather than trying to hide it.

So I went out today and bought two party dresses.  In all honesty, I was in and out of the store in 10 minutes - I hate shopping - and these two looked like they would fit.  And they both fit, just fine.

 Option 1: the purple dress.  My first thought was "love the colour!".  Plus, the horizontal detailing and form fitting nature of the dress was very daring for me.  I love the colour with my eyes and my hair, and it will be a positive shock for most of the people at the office to see me in a colour other than black - any colour. 

The cons are that it really hugs my figure.  Not in a sausage casing way, as there is a lot of room in that dress for dinner, but just in the sense that it is cut in a way that hugs my curves, of which I have many.  I am used to dressing in ways that hide my curves as much as possible, so this is a major mental shift for me.  Plus, as a colour that is almost as far away from black as it is possible to get, this dress just screams for attention, which is a little intimidating for those of us (i.e. yours truly) who spend most of their time trying to blend into the background.  No blending with this dress, no way.

Option 2: the sparkle dress.  This picture does not do justice to the number of sequins in this dress.  Basically anywhere there is gold in the picture, there are sequins that catch the light in a really attractive way.

I was drawn to this dress because it is an A-line dress, and therefore immediately more camouflagey than the figure-hugging purple dress.  And the sequins really are quite pretty.  Plus, I like the amount of coverage in the top area (although I immediately saw I would need to pin the front of the dress together, as it gapes quite open when seated. 

As I look at the photo, however, I am thinking that I look a little dowdier in this dress than in the purple dress. 

Decisions, decisions!  I will, of course, change my mind multiple times between tonight and the night of the party, just because that is the way I roll. 

My biggest problem is that I am so unused to wearing clothing in my size (normally I wear suits 1 or 2 sizes too large), that I am very uncomfortable wearing clothes that actually fit me.  I am not used to clothes that fit appropriately, and are not hanging off me, and I feel self-conscious.  I need to get over that, and learn to love showing off my shape, like normal people.

The Nerd is no use at all, as he (wisely) has taken the position that I look lovely in both dresses.  He's no dummy.