I Don't Do "Stunning"

As New Year's Eve approaches, I am faced with an issue that triggers insecurity in me... fashion!  I wear jeans.  Period.  I love jeans.  I am comfortable in jeans.  I am myself in jeans.  I pair them with a tee, a sweater or maybe a cute top of some kind, but that's it.  I don't really accessorize and I don't tend to branch out into other types of clothing.  It is just beyond me how to put together an actual "outfit."  Oh wait!  I did get a couple of big bracelet watches this year that I love dearly and wear with everything.  That's about it on the accessories though.

Today I find myself attempting not to hyperventilate over the task of dressing myself for tomorrow's big event.  It's one of those things that most women love getting ready for.  It's an opportunity to get all fancy and create a look that is absolutely stunning.  As for me, the simple task of buying a dress is nearly enough to put me in a padded room.  I think it is quite possible I would rather chew off my own pinky finger than go shopping for fancy clothes.

I ended up buying six dresses for NYE and asking opinions from four friends.  Naturally everyone had a different favorite. I think I have decided to go with the dress my date for the evening likes the best (after all, he's the one that has to look at me all evening).

So, now that I think I've chosen a dress I have a number of self conscious thoughts running through my head... Should I wear jewelry with it?  Do I have any jewelry that would match?  What actually does match anyway?  Should I buy something new?  Can I afford to buy something new?  Where do I shop for something like that?  Which shoes should I wear or should I buy new shoes... and if so, what should they look like?  How should my hair look (not that I have many options since I can't use a curling iron to save my life)?  What about makeup?  Should I wear lipstick?  I never wear lipstick.  Will it get on my teeth or rub off in the first 10 minutes?  What if I put all this effort in and still fail to look good (which I have been accused of in the past when I've tried to pretty myself up).  Is everyone there going to think I look like a joke?  Ughhhh.....

My dream is to have a personal shopper/ stylist who will simply pick out my clothes, lay them out for me and make me up when I need something outside of my normal clothing.  Even on normal clothing days, I'd like someone to approve it before I leave the house.  Somehow, I missed the class on how to dress and accessorize.

Hmmm... writing this has been very therapeutic.   I think I am going to just throw on some black heels with the dress, leave my hair and makeup normal and call it done.  Hopefully no one cares that I have completely failed to accessorize or do anything special to myself.

"Simple" and "cute" are more my thing.  I just don't do "stunning."

Update three hours after original posting:  I've decided to wear a different dress.  One that a lovely friend voted for yesterday.  She even sent me shoe and jewelry suggestions for it.  Now that's a great friend!

Update on New Year's Day:  I survived! (But I'm happy to be back in my jeans and hoodie)