I am going to admit something to you. When I am dressing to go out at night I spend too much time figure out what to wear. I stand in front of the mirror in dozens of combinations and fret about my clothes. It's gotten to the point that I start planning my outfit for a night out a few days ahead of time. In fact, I laid in bed last night for an hour thinking about what I'm going to wear on Labor Day weekend when we have several people in town and we will be going out about 3 nights in a row.
So... I'm creating some rules, based on what I know now and what I am trying to incorporate.
1. You have to feel comfortable. Not pajamas comfortable, just not messing with your clothes uncomfortable. I bought the hottest dress a few weeks ago and decided to wear it to a party. The day before I tried it on and couldn't get it to sit right and I felt like I had to suck my tummy in and kept messing with the cowl-neck and straps. I'm taking the dress back.
2. Never wear new shoes when you'll have to walk or you are going out dancing.
3. Only give one hint. I mean, if you have a short skirt then you don't show cleavage. If you show cleavage then wear pants or a longer skirt. If you are wearing skin tight then make sure it covers more area. Note: If you cannot wear skin tight, don't. Please. I have times when I'm bloated or it just highlights the wrong thing too. Don't subject every one else to it!
4. Silk, satin, sparkles, beading, rouching, flashy jewelry, fun make up, fake eyelashes, all those things you want to try but never do? Try it.
5. Consider your surroundings. Boulder going out clothing is much different that Denver going out clothing. Dallas going out clothing is much different than London going out clothing. If you would wear it to a brunch wedding shower, then it is probably not evening wear.
6. Make sure your accessories are right. Get a clutch or a small purse. Your jacket or coat cannot be your normal, every day jacket. I think flats are a no no, but I guess if they are dressy and appropriate I'll give you a hall pass.
7. Learn how to do an updo. Just don't ever use plastic clips to hold it in place. An updo will take a normal outfit and make it much dressier.
8. If you can make jeans work for where you are going then they must be fitted, dark wash, long, straight leg jeans. No pleats, no poofing, no fading, no bagginess.
9. If you ever find a dress you love and think "I'll never have anywhere to wear it", buy it. And always have one of these in your closet.
10. It is always better to be over dressed than under dressed. Always...