Dress to impress yourself: the 10 style rules I live by

I come from deeply humble fashion roots. My parents are hippies for godsake, and I grew up in a mix of dirty hand-me-downs my parents dug up, cheap stuff from Sears, and frilly dresses gifted from my grandma. I preferred the frilly dresses, and my mom had to bribe me to wear pants by telling me that they made me look tall.

Just before I started fourth grade, my folks asked me what clothes I wanted for the school year. I shrugged and replied that my favorite outfit was a lilac polyester sweat suit from Sears, and really all I wanted was several more of those. And so I spent all of fourth an fifth grade in rotating lilac sweatshirts and sweatpants. That was all I wore for two years. Thankfully, I eventually came out of this phase, and after 25 years or so, found my way to a sense of style that feels comfortable and authentic. Here are the rules I live by. What are yours?

1. Comfort is king.

Ok, I moved out of my lilac sweatpants phase, but retained one truth from that era: if you’re not comfortable, nothing else matters. Uncomfortable usually equals unflattering. Pants that dig into your love-handles and make a muffin-top? Uncomfortable and ugly. Tight shirts that ride up and expose your lower back and belly? Cold and unflattering. Your clothing needs to be comfortable both physically and emotionally. You should feel good in your clothes. Confused sometimes (“Did I really put a skirt on as a poncho?”), but good.

2. Style isn’t about clothing — it’s about confidence

You can wear absolutely anything if you sell it hard enough. My brain sometimes boggles when I see fashionistas wearing the most patently unflattering, heinously ugly clothes — but they walk with confidence bordering on arrogance and somehow manage to make it work. I might think they look ugly, but I can’t deny that it’s stylishly ugly. Moral of the story: wear what makes you feel confident, and you’ll look stylish.

3. Avoid uniforms

I don’t like being easily identifiable by my clothing. Back in 2000 or so, I wore patchwork dresses around Olympia, WA and everyone would assume I was a hippie student at Evergreen State College. It gave me great pleasure to say “Actually, I’m the editor of a rave magazine in Los Angeles. But thank you for asking.” Since discarding the raver template, I’ve developed an aversion to being pigeonholed by my clothing. Keep ’em guessing. Create your own template.

4. Custom-made clothes and indie designers are the best

If I had unlimited amounts of money, I would not spend it on designer clothing. I would spend it on having a personal seamstress/designer who would make me all my clothes. Clothes made to your measurements fit like nothing else. And buying from indie designers is a great way to support artisans while wearing unique awesome stuff. Forget international designer labels: go custom and indie.

5. Remix what you’ve got

Fashion can all-too-quickly become consumerism, but it doesn’t need to be that way. Your closet has more fun outfits than you know — don’t be afraid to mix things in unexpected ways. Buying your clothes by pre-set outfits will be the death of a creative wardrobe.

6. Play with your clothes

Try to maintain a sense of curiosity and play with your closet. That skirt — could you layer it as a strapless dress over a t-shirt? Could you wear that belt as a tie? You will doubtless leave the house looking ridiculous sometimes (God knows I do) but fashion isn’t for taking seriously. As long as you’re laughing and comfortable, no one else matters. Which brings me to my next point:

7. Dress to impress yourself

Make your peace with this now: no matter what you wear, someone is going to think you look stupid. Seriously. Everyone’s a member of the fashion police, and no matter how carefully you follow trends or how hard you buck trends, someone is going to think you look bad. So stop caring and just dress in a way that makes you happy and comfortable. Even if I think you look ridiculous in those pants, it doesn’t matter if you love them and find them comfortable.

8. Shop by material and construction for basics

This is one I’ve learned the hard way. That asymmetrical cowl-necked sweater I ordered online? SUCH a great design, but made in China cheaply out of polyester. I’ve learned that it’s worth it to spend on basics that are made out of quality materials like merino and cashmere, and solidly constructed to last for a long time. Accent pieces can be silly, but when it comes to the base layers? Focus on materials and quality construction.

9. Beg, borrow or steal your fashion from others

Inspiration is everywhere. Look for people with your same body type who look good in their clothes. Feel free to ask them where they got particular articles of clothing. Feel free to steal their look — it’s ok as long as you give ’em credit.

10. Look to the fringes for accents

I wear a lot of basics, and probably the only reason anyone thinks I have any sense of personal style is because a lot of my accent pieces are inspired by my favorite subcultures. The internet is of course awesome for this sort of thing. Why didn’t anyone tell me about Dark Mori sooner?!

Those are my 10… what are yours?