Dressing for Success

I’ve always been the kind of person who dresses for comfort. Not necessarily for style or anything else. Sometimes it’ll look good, like I meant to put it together that way, but mostly, it’s jeans that are too big and a tee shirt that might or might not have holes in it, and a pair of chucks.

This weekend, Amanda and I went shopping to buy me new jeans, as my old ones are so big that I have to cinch my belt incredibly tight to keep them up. Yay!

So I tried on my new jeans for my girlfriend, a new experience in itself, and she approved of the way they fit on my ass. Therefore, we bought them. And I wore one of my new jeans and the tie that Amanda picked out for me to dinner at my friend Scott’s. I felt awesome. I was wearing new jeans, a new tie… my girlfriend couldn’t keep her eyes off me… Its a kind of heady feeling.

And today, I had to go to a business meeting with my boss so I had to ‘play dress up’ – my boss’s words, not mine.  And this is what I went with.


Black button up shirt, grey sweater, same new dark purple tie that Amanda picked out Sunday, and my hair up in a messy bun.

And all of a sudden, I felt like an executive assistant! (That’s my job title for those of you who don’t know).

So then I got to wondering, do the clothes really make the person? Or does it require an understanding of yourself for the clothes to bring you that rest of the way?

I enjoy dressing comfortably. I enjoy dressing up. But there’s no reason the two have to be mutually exclusive do they?

Of course not. And I have a girlfriend who likes people who dress in the way that I enjoy. She loves mens’ dress clothes, and I just happen to look fucking hot in a vest and tie. She’s also a girl who likes to shop, but also understands my limitations in that arena. (And best of all, respects my limitations!) But she has no trouble picking out clothes for me that look good, that fit well, and appeal to her.

And now I have  cologne. 😉

Also courtesy of Amanda, my Valentines Day Present a bit early (remember when she got hers a bit early too?)

Right now, even wearing my new jeans, my black shirt, grey sweater, purple tie, and black dress shoes, I feel classy and sophisticated, and yet casual and comfortable all at the same time.

Is this what dressing like a grown up is supposed to feel like?


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