I saw a girl this morning, hipster-type, getting out of her car. She was very put together with an outfit in earth tones--browns, reds, a stylish cap. And she was wearing orange lace-up cloth boots that came to her lower shins. Her pants were sort of askew and half tucked in to the boots.
It worked. It was obvious that the boots, and the pants' arrangement, were deliberate. I think a few things factored into this obviousness:
1. The rest of her outfit was obviously well thought out.
2. She carried herself with confidence.
3. The contrast between the boots and the rest of the look was so substantial that it almost had to be deliberate.
What can we learn from this?
1. When you deliberately break a rule of normal dress, you have to believe in your ability to look good while breaking the rule. If you don't carry yourself with confidence--and you won't unless you believe you can pull the rule-break off--it's more likely to look like you failed.
2. Keep the rule-break simple. Otherwise, you run the risk of looking like you deliberately picked random stuff to mix together.
Decide how hard you want to push, and then push harder. And then own it.