3 Ways to Dress Your Best (most fun and favoritest) Self

By: Amy Kennedy

Have you ever looked at old pictures and wondered what the hell you were thinking wearing those pastel striped pants? Or, is that only me?

Yes I have a picture of myself in pastel striped pants, no, I will not post it here! I dubbed them my "clown pants" because, well, they made me look like I escaped from a circus.

Was that really the way I wanted to look, or was it easy and maybe comfy and no thought had to be involved? Yeah, I'm thinking all three of those.

Now, think about a picture or a time when you were wearing something that made you feel fabulous--something that garnered compliments from others, something that made you feel like your favorite self, your true self.

Don't you wish you could have that feeling more often? Of having your inside self be your outside self, or maybe having your outside self help your inside self get where she wants to be?

Look, I know looks aren't everything, neither are clothes or shoes or jewelry. But they sure the heck can make me feel good!

I have recently come to the conclusion that the reason I adore Halloween is it allows me to dress like parts of my inner self.

• Sometimes I'm all connected with the power of magic and I like to dress as the personification of that by donning a pointy hat and wearing black and holstering a magic wand. 
• Sometimes my magic comes through in a different way, with bright colors and scarves and lots of jewelry.
• And other times I like to be the adventurer, the seeker of knowledge, so I dress in vests and goggles, with plenty of gadgets at my waist...you get the idea.

All these "costumes" are really my fun inside me shining through to my outside.

In extreme.

But, once I figured out why I liked to dress up for Halloween I figured out how I could always have fun while dressing as the "me" I was on any given day. And in case you missed it, the operative word is FUN.

FIRST: 

LOVE your clothes. I am not even kidding, why wear meh when you could wear YES!? This is a tough one--people gift us with things we feel obligated to wear, right? All the time! And if it's our child, we feel even more obligated, ouch. 

So here are some scripts I am gifting to you: 

Thank you! (yup, that's it. If you rarely see them, just say thank you and then return it, if you do see them all the time, explain you had to exchange it, as it was too small, there was a small hole, it didn't look right on you, and leave it at that)

Okay, I only had one script for you--Thank you. It's really the best though, unless your husband gives you a brown fleece zip up jacket, then you say, "Really? Fleece? I will never ever wear fleece." But that's not the greatest script.

SECOND:

Do not own too many clothes. Once again, I am not even kidding. You dilute your wardrobe with too much detritus. I always need to relearn this one, I love going through my clothes at the change of seasons--I actually see what I have, I decide if I still L.O.V.E. each thing and if anything needs attention. 

Have you ever shopped in a store where you could barely move the clothes on the rack to see the next item? Well that's what happens in your closet--too many clothes EQUALS "I have nothing to wear."

THIRD:

Have fun. F U N. Add things that make you smile. That give you joy. I have an off white scarf with pink skulls on it. 

I adore that scarf--and I love to wear it with pearls, that's part of my fun with clothes, a sense of irony. I add two or three pins to my jacket du jour--a cameo and a name crest and an old school girl scout pin (they don't have to match, but there could be one thing about them that ties them together). 

I usually try to keep FUN to accessories, but sometimes it crosses over to actual clothing--the only thing to be careful of with FUN articles of clothing is they might not actually GO with anything. I have an awesome gauzy shirt. 

But I can wear this with jeans, black dress pants, I also wear different shells under it, black, orange, green--that changes the look of it.

That's it. For now. Next time I touch on style I'll dive more into the "themed" dressing, aka a Halloween closet.

What's your biggest wardrobe style challenge?