I was recently talking with some male colleagues and during the course of the conversation it was revealed that they are more successful at being a woman than I am.

Well, maybe not being a woman, exactly, but certainly in investing in themselves. (We’re talking custom tailored shirts, countless shoe options and tremendous watch collections.) When it comes to fashion, they have absolutely no trouble spending money on themselves.

Wait, what?!

Custom tailored shirts? Boxes of  shoes? Multiple watch styles?

OOPH.

It’s just not right.

When it comes to wardrobe, I’ve always been the kind of gal that just gets by. I rarely go on shopping sprees. (Unless grocery trips to Costco count.) Most of my clothing is supplied by other people at the end of the year in the form of birthday and Christmas presents.

It’s sad.

It’s really, really sad.

No clothes

I’ve been thinking a lot about this subject lately. Mulling over the unfairness of it all and I’ve come to a conclusion – it is my own damn fault.

It also has everything to do with my mother.

My mom raised four children on a cop’s salary. She never (and I mean NEVER) spent money on herself. Her uniform (until she started working later in my life) was an old T-shirts and jeans. And I have vivid memories of my eight year old self helping her color her hair. (Pulling hair through that weird shower cap thing. So. Not. Fun.) 

Mom was frugal and practical almost to a fault. She never wanted to “waste” money on herself. See? I come by it honestly. I feel a tremendous amount of guilt when buying clothes for myself. I just can’t seem to shake the feeling I get of being selfish when shopping.

There is one more thing, though. If I’m being tooooootally honest, I have another issue that keeps me from investing in myself – the whole “I’ll do it when I lose 10 pounds” thing. (I’m sure you can’t relate.) I have reams of clothes in my closet that I can’t wear.

REAMS.

My wardrobe is pretty much worthless.

I seem to be under a multi-year delusion that I’m going to permanently loose 20 pounds, look like a model and then fill my wardrobe with sexy, professional options.

Until that time I will try to get by on as few options as I can so that I don’t (you guessed it) waste money.

Reality check, anyone?

This is definitely something I want to focus on for 2015 – learning to invest in myself. It has been an issue I’ve long fought and really need to GET OVER ALREADY. It won’t make me a bad person to actually want to be presentable.

I need to just bite the bullet and pull out the credit card. (Anyone up for a shopping trip?)

How about you? Do you spend money on yourself? Or does guilt keep you from being your best?