Here are some of the most common "fashion rules", and how to break them with panache.
Fashion Rule #1: Lame (I can't figure out how to put an accent over the e so imagine that there is one there!) leggings will make you look like a ho-ish ho-bag.
Though this is a relatively new issue (thanks, American Apparel!), I felt that it was important to address. There is a (logical) misconception among some that clingy, shiny leggings will give off that not-sought-after prostitute vibe. However, if worn right they can be absolutely chic.
Avoid wearing them with shirts that fail to cover your butt, high heels, or anything else shiny.
Try a look like this:
A soft sweaterdress creates an interesting textural contrast and downplays the harsh-ness of the leggings. Make sure that it's baggy and not clingy. Girly accessories like the necklace above soften the look, while flat leather boots look surprisingly good with the combo.
Fashion Rule #2: If you mix patterns you will clash and look horrible and everyone will hate you.
This is the mother of all fashion rules, repeated over and over again by people whom are likely fashion wimps. Mixing patterns can look amazing. Here's an example of how to not look like a clown:
Stripes and plaid and polka-dots, oh my! However, it works because the clothes stay in the same colour scheme, the general feel of the outfit is playful and fun, and not all of the patterns are bold. If you're going to mix patterns, make sure that one dominates while the others stay low-key.
Fashion Rule #3: Socks and sandals should never, ever be paired together.
This is a rule that I personally took it upon myself to enforce as a child, by whispering about the socks & sandals wearer loudly and in a horrified manner to whoever I was with. I'm still not saying that your father's black socks and Birkenstocks combo is on trend. However, peep-toe heels with bright coloured tights, over-the-knee socks, or ankle socks can be surprisingly cute. Try if possible to get a pair of socks where the seam is not at the toe.
Fashion Rule #4: Wearing denim on denim screams "hick".
I still can't claim to be a fan of denim on denim, simply because I'm not really a jeans person to begin with. However, if you're going to do it you might as well do it right.
Make sure that the washes of the denim are really, really far apart. If they are similar shades it will look like you tried to match, and if they're the same shade, you are wearing what some refer to as a "Canadian tuxedo" (never a good look). Wear a long tank or tee under the jacket to create space between the denim. Top the look off with a pair of killer heels, simply because they are awesome.
Fashion Rule #5: Black and brown look terrible together (as do black and navy blue).
I don't even know how this rule came about. All of these colours are neutrals, and neutrals can be paired with anything, including each other. Make sure that the shades look nice together and that the feel of each piece works with the outfit that you have selected, and that's that. For instance, a tan satchel, black boots, and dark navy jeans look great together.
Remember, by no means do I intend for my tips to become the "new" fashion rules. If you want to rock your medium-wash denim jacket with your medium-wash jeans, more power to you. (Just don't expect me to follow suit!) Fashion should be fun! Enjoy it!