May Day maydays: Fashionista crash and burn ...

To learn more about the actual celebration of May Day, visit http://en.wikipedia.org/wiki/May_Day

Today is the first of May, May Day for those of you who celebrate the pagan-turned-Christian holiday. And there are several times throughout my 40+ years where I -- thinking I was some fantastic fashionista -- crashed and burned. Here are a few of my not-so-fantastic fashion-after-40 moments, a kind of recap on my fashion "maydays" on this beautiful May Day if you will:

Stilettos and platform shoes
Pro -- they look sexy
Con -- I'm torn between not wanting to break a hip and they are just so uncomfortable

Skinny jeans
Pro -- everyone is wearing them
Con -- why would I want camel toes

Hair extensions
Pro -- looks good from a distance
Con -- You know your girlfriends are laughing at you because last week you were sporting a pixie cut and this week you look like Rapunzel. Um, who do you think you are kidding?

Funny slogans on T-shirts
Pro -- you like to express your sense of humor (my favorite T-shirt,  that I only wear at home, shows a little "chick" marshmallow Peep with glasses that says "chick with brains" -- given to me by my BFF, Molly)
Con -- let's not mistake sense of humor with sense of style

Uber short shorts
Pro -- They are the trend and I want to be trendy
Con -- My mom always told me that just because something was out there, didn't mean I should have it. I apply this logic to the uber short shorts (you know the kind, where half your buttocks are hanging out the back) and a host of other fads. Yes, uber short shorts are made by designers and they are available to me, but that doesn't mean I look good in them or should purchase them.

Fancy workout wear (e.g. Juicy Couture velour sweatsuit)
Pro -- It's Juicy Couture and you are hip to the 20-something style
Con --  It's Juicy Couture and you look like you are trying to be a 20-somethingwhen you are really 30+, 40+, 50+, etc. (my sister would be mumbling something about "mutton to lamb" about now)

Blinged out anything (e.g. baseball caps, jackets, etc.)
Pro -- It is unique and eye-catching
Con -- Do you really want to look like you let an 8-year old girl and her bedazzle gun get a hold of your clothes? It warrants people to ask, "who is your fashion designer, a Disney Princess?"

Team spirit clothing outside of sporting events
Pros -- Wearing your favorite football, basketball, (fill in sport here) team colors or name across your chest shows your loyalty and team spirit.
Con -- Why would you sacrifice your elegant and fabulous style (outside of an actual sporting event) to provide free advertising to sports stars who already get paid ungodly amounts of money to throw balls, catch balls and run?

A $2,000 purse
Pro --  You can claim you have a luxury item from premium designers like Hermes or Louis Vuitton
Con -- it doesn't matter how much you paid for a purse, it will still get filthy on the inside from lipstick tubes which lose their caps and pens that pop open and write hieroglyphics on your beautiful lining

Legwarmers as streetwear
Pro -- Great if your job is prima ballerina or you are going to a costume party as the 1980s Flashdance girl (Jennifer Beales)
Con -- If it's that cold outside that your ankles get cold (and not any other part of your leg) you have bigger problems than a fashion  faux pas (in other words, go put on a pair of pants)