How to look pretty without looking like you tried
In my early days one of the best compliments I would get from women was about how my I would look fashionable without trying. Of course when you are young it is easier to look pretty without even trying, but it was more than that. I was able to put on a bunch of non-coordinated items and looked fashionable. This was the pre-time of street fashionistas and the trend of mixing prints and colors and the messy bun. That has been my style since I was born. Unfortunately now it has been done so many time that it lost meaning to me.Now, it is harder to pull a messy look without actually looking messy, especially at work, but there are some some items you should have in your wardrobe that you can mix and match without putting too much thought into it.
I personally feel comfortable with an urban style made out of dark skinny black pants, ankle boots, a white loose top, and a leather jacket. Top it with a pashmina, a cool hat and jewelry and you are done. That is literally how I feel cool. Unfortunately, this look does not quite go in Florida because of the weather and the environment. It's fascinating how the environment influences your fashion style. For example the Caribbeans are popular for bright colors, while norther countries rely on cold, dark colors.
I feel my wardrobe is a mess in terms of outfits for the 'correct' environment but here the top must items to look always good without trying and I do own those must have items.
1. Pashmina or light scarf: If you don't have one go and buy one. It can change your outfit completely, add glow to your skin or attitude. You can have prints, neutral colors and different textures. The one below in the picture is from ModCloth for $19.
2. A good pair of shoes: I know you might think "duh" but I mean a pair of shoes you can walk in comfortably whether they have heels or not. Own the catwalk, don't let the shoes dictate how you walk. Take a look of those sandals by DG. You can still pull off a kick ass outfit and be comfortable. I would pair these sandals with dresses, pants, skirts, everything.
3. Some type of Blazer/Jacket: It could be a leather jacket, which everyone should have in their wardrobe, or a nice blazer. Even a cardigan can add to an outfit. Especially if you are wearing just a simple pencil dress. I like this Chiffon Layered Open-Front Cardigan for $47. Alternatively I love this asymmetrical blue leather jacket by Helmut Lang.