Most fashion and personal style rules are all about making you look better. And although it’s important for your clothes to make you look great, it’s also pretty important for them to make you feel great.

After all, the two go hand in hand. It’s hard to make a killer impression when you’re wearing an outfit you hate, even if that outfit is a designer masterpiece that’s right on-trend.

So, instead of focusing on when you can wear white shoes or what silhouette works for your body type, consider these personal style happiness rules.

1. Find what you love

It can be challenging to feel good about yourself and your appearance when you don’t really know what you like. If that’s the case, shopping can be miserable and getting dressed can feel like torture. But it all gets a lot easier and more fun when you know what kind of clothes you like.

What colors make you feel good? Are you into a vintage style or do you like modern trends? Do you have a preference for certain shapes or fits? If you don’t know the answer to these questions, it may help to think about what some of your favorite outfits or pieces have in common, and then look for other items that have the same qualities. If you’re totally lost, consider consulting a personal stylist who can help you refine your tastes.

And once you figure out what makes you feel like a million bucks, don’t doubt or deny yourself by saying things like, “Is this too much? Do I look silly?” If wearing vintage style dresses or big hats or bright pink makes you happy, do it whenever you possibly can.

2. Take risks

While you should absolutely hone in on a signature style you love, it’s important to occasionally take risks that push you a little outside your norm. If you don’t, you risk falling into a rut. The wardrobe you once loved starts to seem boring, dull and uninspired. That’s when you start shouting things like, “I have nothing to wear!” while throwing around dozens of items that clearly indicate otherwise.

Here are a few non-scary ways of changing things up:

  • Pair items you already own together in new ways that you haven’t tried before.
  • Buy a piece of clothing in a color you don’t currently have.
  • Try an item in a silhouette you love with a bold color or pattern you don’t normally wear.
  • Opt for textiles you haven’t worn much before – leather, suede, linen, etc.
  • Take risky new looks for a test drive in a low-takes situation, like dinner with your bestie or a family part – if it flops, no big deal.

3. Don’t be self-conscious or uncomfortable

We’ve all done that thing where we buy or wear something because we think we should. But as soon as you actually leave the house in it, you feel totally insecure or physically uncomfortable. The lesson here is that no look is worth more than your happiness.

If you know that you can’t stand high heels or that body con dresses make you want to crawl in a hole and hide, then don’t force yourself to wear them. The discomfort you feel will make any potentially cute outfit look kind of blah. Though it’s good for you to take risks now and then, draw the line at pieces that cause pain or self-doubt.

4. Stop stressing over “the rules”

Yes, I realize that an article about style rules telling you to disregard the rules is a little strange. But if you want your clothes to contribute to your happiness, you have to have a healthy spirit of rebellion. Some of the most fashionable people in the world are considered stylish specifically because they break the rules.

If following accepted style Dos and Don’ts helps you, then keep at it. But if thinking of those guidelines feels limiting or gets you all mixed up when you’re trying to figure out what to wear, then give yourself permission to throw the rulebook out. Of course, you should use good judgement when it comes to what’s appropriate, but forget about things like, “Don’t wear navy and black together” or, “Avoid horizontal stripes.”

5. Do annual wardrobe reviews

A wardrobe is supposed to be a dynamic thing, so it’s a good idea to do a yearly review of everything you own. Not only does this help you make room in your closet, but it also prevents you from feeling bad about things you no longer wear.

If you experience negative feelings when you look at pieces that don’t fit you anymore or items that you bought but later decided you didn’t really like, it’s time to chuck them out! If you haven’t worn the thing in a year or 2, chances are you’re never going to wear it again. And you’ll feel much better when you open your closet and see only things that you genuinely love to wear.

Clothes can be a real source of joy in your life. When you put on a fabulous outfit that you love, you instantly feel happier and more confident. So, if your wardrobe is a source of stress or insecurity, it’s time to rethink how you shop and dress. By implementing these simple rules, you can make sure that your outside and inside are equally gorgeous

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Author: Liz Kores

Liz Kores is the managing director of Oak Street Chicago, a business association that represents some of the finest designer boutiques, hotels, spas and restaurants in the Windy City.  She is also on the board of the Chicago Fashion Incubator and a frequent guest blogger on a variety of online style publications.  For more, visit

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