<---- {That disaster was, thankfully, for a school spirit day.}

For a long time, I found myself totally confused about what to wear. I read magazines sometimes, and they always seemed to conflict. One said don't wear white after Labor Day, another insisted that rules are made to be broken. I often wouldn't know a trend if it fell out of a tree onto my head, and the ones I did pick up on were usual transient and looked silly on me the following year. When I tried to go the extra mile every once in a rare time, I found myself feeling over-done and felt like I was projecting an "I try wayyyyy too hard" vibe. Even more than that, my fancy frippery was often itching me, giving me a blister, or getting me inappropriate attention from supermarket cashiers. What gives?

Now a bit older and hopefully quite a bit wiser, I'm finally starting to understand what having good style is all about, and moreover, learning what makes me feel good when I wear it! I'm not here advocating any one thing--not reading Glamour and taping the Do's and Don'ts to your wall, not dressing just like your best friend (that will drive her crazy in about .5 seconds), not dressing to please your boyfriend (that will drive you crazy in even less time), and not just shopping thrift or vintage, Gucci or Prada. Nope, I'm advocating some simple tips that will help you adjust your wardrobe and how you wear clothes in a way that makes you HAPPY instead of being confusing. Getting dressed should be an adventure, kind of like painting a canvas or visiting a new place. It's either a beautiful way to express yourself and feel good about what you're saying with your clothes or it's a pain in the butt. Which that will be is up to you! So here they are, my ten tips for dressing to feel (and as a consequence, look) great!

1) Never wear anything that makes you uncomfortable, no matter how fashionable.
This might seem like beyond-obvious advice, but you'd be surprised how often you aren't taking it. Something that makes you uncomfortable is any article of clothing that you are constantly tugging, pulling on, or adjusting to make sure it looks right. Sure, a scarf in your hair might need adjusting or a strap might slip off of your shoulder, but this shouldn't be the normal operating function of that article of clothing. If it typically malfunctions, toss it or give it to someone who fits. This qualifies all pants that are so tight you can't eat a meal, much less sit down to pants that are so baggy you keep pulling them back into place (I'm way guilty on the latter from time to time).
This also goes for shoes that hurt your feet excessively. Sure, we all might suffer a bit for our highest heels, but if they make your feet hurt badly enough to blister, bleed, or otherwise make your feet look like war-victims, take them off and get some new ones, honey! One of my dear friends and college roommates worked at a shoe store and her devotion to cute flats of all kinds ripped her feet to shreds. She really regretted reopening blisters when it got to the point that she was bleeding all over the place when she took her shoes off. It sounds extreme, but it can get there pretty quick if you aren't careful! Your feet carry you everywhere, be nice to them and you will be more mobile and happier too.
Lastly, if you just don't feel like a particular style or outfit is sending a message you want to send, don't wear it! If you feel odd wearing stuff that is too flashy, don't. If you don't really like a trend and feel self-conscious in it, don't wear it. You know what's right for you. However, be aware that a constant feeling of discomfort in your clothes or a feeling that nothing looks good on you could be a moniker of low self-esteem and be sure to address that if it is the case.

2) Dress for the occasion.
If you stayed up all night writing a paper and you're going to class feeling like a zombie, a good pair of sweats is your new best friend. For giving a presentation? Not so much. Make sure your clothes project seriousness and realistic notions about what you are doing. If it's a job interview, dress conservatively and take great care that everything is pulled together for a clean, classy look. If it's yoga night at the Y, do not wear blingy but give-you-such-a-big-wedgie designer track pants. Just wear what's comfy, which might be a big t-shirt and some jersey knit shorts. Your call.
Dressing for the occasion will make you a happier dresser because you feel prepared and appropriate. When you know you are wearing what will help you be comfy and confident, it helps you focus on the task at hand. So enough wearing stiletto boots to "hike" and crawling into your job looking like you don't care if you get paid or even seen for that matter. Project consciousness of the occasion and you will feel good about yourself.

3) Know thyself.
Take some time to really evaluate what you wear. Do you shy away from certain colors? Why? Do you prefer certain styles? Why? A little thoughtful meditation on your little unwritten fashion rules will say a lot about your personal style. If you don't wear a lot of color, why is that? Try different colors and styles, even if it's just in the fitting room, and get an idea of what you look great in. Then...wear it! Don't wear shiny leggings if you know you will look like a Vegas showgirl. Don't wear wide-leg pants or skinny jeans if you know they don't really flatter you and you don't like them. To thine own fashion truth be true. It sounds corny, but you know what you like, you know what you don't, and trends shouldn't sway that opinion too much. Maybe you'll like one or two and that's great, but don't make them your fashion guide. You are your own best stylist.

4) Get inspiration.
Feeling stuck? Breathing fresh air into your style will make you happier about what you're wearing if it's been same-old, same-old for a while. Try getting some style inspiration. I suggest the following blogs and photographers that I like for personal inspiration. Sometimes it helps to see what other people are wearing to know what you want to wear!

- The Sartorialist
- Street Peeper
- The Cobra Snake
- Shark Vs. Bear
- Wardrobe_Remix on flickr
- Hel Looks
- The Fashion Ramone

I could go on, I read wayyyy too many blogs. Post your faves in the comments too!

Reading fashion mags can be great too, but don't get too stuck on "rules." Just look at the pics and see what pops out at you! I really like Nylon, personally.

5) A caveat to dressing for the occasion: don't dress for anyone else.
I touched on this a bit above, but while it's good to be appropriate for where you are going/what you are doing, it's not good to dress to please somebody else. Obviously dress codes are a fact of life, but I'm talking about not wearing red because one time a rude friend said it looked bad on you, etc.
When I was in 9th grade, my frenemy "best friend" told me she thought a sweater I had bought the day before with great glee to wear to school was tacky. It probably was a little tacky, but that's for my twenty year old self to now say, not the fourteen year old the next locker over. I never wore the sweater again, but I should have! If you really like something that your mom, your boyfriend, your friend, whatever--doesn't like, just brush it off. Say, "Well that's your opinion but I really like it." If they really care about you, they will probably shrug and say, "Ok." and not mention it again.
This is not to say you shouldn't heed decent advice. If your BFF pulls you aside to tell you that your shorty-short skirt keeps flashing people, she's probably just trying to spare you a little fashion embarrassment. Don't flip your lid, just maybe think about it some. You know in your gut what is helpful advice and inconsiderate meddling.
On a side note, consider just not having people in your life who make you feel this way! That boyfriend who mocks your hippie dress in anything but a totally joking way might just turn into your husband who makes fun of much more than that. Maybe, maybe not, but once again--you know when someone is being helpful and when they are just being critical. Give the naggies the boot and live a simpler life.

6) Get a little wild.
Know when to just try something crazy. It will cheer you up to wear something that is a little out of the norm for you, and an occasional impulse-buy or weird outfit day could be just what the doctor ordered. You might find out you really like purple scarves or crazy printed tights or that big gold necklace! You might even find that other people notice your fearlessness and applaud. Believe that haters are just people who lack personal bravery, and that most people just enjoy confidence. It is true.

7) Use your clothes as a means to an end, not the end itself.
Getting dressed shouldn't be the end of the story. Getting dressed is the beginning. For many people, particularly women, getting yourself adorned and ready for the day can be calming and help you set the tone. Don't see getting dressed as mundane, see it as an opportunity to set yourself up for a great day by decking out for it. Sure, not every day affords us an hour to get dolled up exactly the way we want, but when that happens, take advantage of it. Get dressed not just for the sake of getting dressed or even for the sake of looking fantastic to others. Get dressed because you see it as a way to put on your armor, to prepare and inspire yourself for the day. Looking amazing is well and good, but it's not worth anything if you don't make it worth something. Know what I mean? No?
See each day as a blank slate and use your clothes as a tool to make that day colorful, beautiful, and amazing. At the end of it, it won't matter what you wore, it will matter what you did. The thing is, dressing yourself can be a way to start the process of doing your best all day long. When you suit yourself up in an inspiring way, you start your morning off refreshed and ready to go. You are prepared and you know you feel super about what you look like. This will put a spring in your step and get you off to a good start. It leaves you to focus on what you are doing, which is so much more important. I know if I feel like I look yucky, I focus on it a lot during the day instead of being comfortable, confident, and focusing on the task at hand. Don't let it be about the clothes, let it be about what they can do for you mentally. This is the best tidbit of advice on this whole list, as far as I am concerned.

8) Leave your hang-ups at home.
Confidence is the sexiest thing you can wear. No matter how many times the mags say it, we never believe them. I wonder if this might have something to do with the fact that they are pushing this next to another article about pleasing a man and behind a cover of a beautiful woman who they have airbrushed into robot-like proportions. No wonder you don't believe them.
If you believe that you look beautiful, and EVEN MORE that looking beautiful is only the very tiniest surface detail to the full depth of the lovely and impressive woman you are, you will be radiant on the outside too. Get dressed and then walk like you own it. Don't let your size, your smile, your skin--anything that you are hung up on--change that swagger. You have what you have. You've done the best you can to maximize it. Now move on and realize you have gobs more to offer the world than what you're swathed in on the outside. Sometimes the first step to realizing this is to present yourself well. It gives people a good impression and you can move on to showing them that you are so much more than that sweet little pencil skirt you scored at Salvation Army. You have to believe you have something to offer, and if you don't feel that way, you have to fake it till you make it. Quit talking badly to yourself, quit walking like you don't own the sidewalk.
My friends tease me about my own particular brand of swagger, but ultimately I'm thrilled they notice. I want to be confident and look confident too. It says so much to me when a beautiful woman is talking, sitting, or walking in a way that betrays she is super conscious of what everybody around her is thinking about her. Stop it! You know you are doing the best you can, you know you are truly a great person, you know you are worthwhile. The rest...is just details. Get your swagger!
Just a caution, I am not advocating being self-important, merely knowing you look good and not stressing out about it. Too much swagger makes you look like you don't care about others, but a genuine smile and being heartfelt in all your conversations offset that easily. Practice it.

9) Price and brand do not denote value, quality, or much else, frankly.
If you're obsessed with labels, now is good time to break the habit. Dressing shouldn't be a who's wearing the priciest frock game, and even if others think so, you don't have to buy into it. Buying clothes with labels emblazoned on them is pretty much what it looks like--giving a company advertising space on your body. If you don't advocate their business practices, their ethics, their general style, or whatever--I say don't put that on your body!
Items from mall stores aren't necessarily better than something you'd find at your local Goodwill. Items on the high-end fashionistas of the celebrity world can be replicated for a cheaper price. Don't try to keep up with a game that's never-ending. Wear what you like, pay what you can afford, and tailor things if you want them to look expensive. When clothes coordinate, are clean and pressed, and fit you perfectly, they look like a million bucks, regardless of the actual price tag damage. If you truly like what you're wearing, it will show, and you won't feel shown up by someone wearing something more expensive than your own frippery because you will know you look good regardless. Status symbol clothing is a joke--buy it if you like it, and if you don't, DON'T! Not living by these rules mean that you are stuck in some kind of high-school hierarchy where the coolest girl has the richest daddy and the latest "it" finery. You don't need to re-live that, so let it go.

10) Have fun.
You would think this would go without saying, but just don't take it all too seriously. That's the main thing. Feeling great about what you are wearing is all in knowing that it really is JUST clothing, just an adornment to top off a vast inventory of great things about you.