Oh Make Me Over …

As my personal transformation continues (whether I want it to or not), I realize there is one thing that I have yet to do: completely and drastically change my look. It’s makeover time!

(For one who now spends her days in yoga clothes, makeup free and in a ponytail, this should be interesting.)

I have an inconsistent history when it comes to breakovers — changing my look in reaction to, or following, a major life event such as a breakup. (In case you haven’t noticed, I’ve had a few “major life events” lately). I’ve been known to cut off a lot of hair and go much darker following a romantic breakup. You know, because I am edgy and tough. Sometimes the new look worked, other times … not so much.

In preparation for my wedding, I had grown my hair long for what felt like years, so I cut it all off once it was over and tried out the “Pob” — the bob style that Victoria Beckham, AKA Posh Spice, was rocking at the time. While I liked my short hair, the simple reality is that I cannot function without the ability to pull it back into a ponytail. I woke up every morning looking like a mushroom head, and was not about to wash/blow-dry/style every day to get it to look anywhere close to normal. So, lesson learned — the shortest I will ever go again will still be long enough to pull back.

As I consider what to do next, a few things come to mind.

• Why? Well, why not? I’m bored. My short hair grew back years ago. I’m also now a “suddenly single” woman in my late 30s. Time to mix it up.
• Risk tolerance? When it comes to color, anything goes. If I don’t like it, I’m only stuck with it a few weeks. In terms of cut, I will go shorter, but not so short that I can’t wear it back / in a ponytail.
• Level of upkeep and effort? Um, well, the reality is that the vast majority of times I leave the house these days are for yoga, trapeze or Whole Foods. Meaning, I don’t care how I look. Even now, when the opportunity to actually *go out!* arises, I am fine taking the time to make myself pretty. Those days are very few and far between, as opposed to when I had to go into the office every day (shudder).

Turning to The Google for inspiration and to see what looks were out there, I came across the InStyle Hollywood Makeover application. Holy time suck … and holy fun!! Check out the gallery below to see a few potential “new looks” based on celebrity styles. I assume the makeup artist and hair stylist are included with these makeovers?

(note: I couldn’t figure out how to have the photo caption/description appear with each picture, so click on the “i” in the upper right corner to see who had the original hair and makeup look)

I am not at all ashamed to admit I spent several hours playing around with this

So, although most of those looks are unattainable given my nonexistent hair and makeup skills, I think I am going to go for a darker color (meaning, closer to my “natural” color, whatever that is). But in terms of style, I have no clue.

Thoughts? If I had to choose, I think these are three of my favorites (and probably, the ones that look most like what I actually have right now … in my wildest dreams anyway):

Inspired by Claire Danes

Inspired by Jessica Biel

Inspired by Sarah Jessica Parker