I think that, except for specific cuts of clothing for shorter-waisted petites (I love petite dresses, because they don't 'pooch' at the back zipper or have too much height at the shoulders) - I think it 'dressing petite' depends a lot on your frame, and your overall silhouette. There are girls who are 5'4"-5'6" who look tiny and I think probably should follow petite guidelines and avoid bulky bracelets or crazy-large patterns, so that they don't look overpowered by what they are wearing.
I am 4'11", and a size 4. Most people think I am taller - I think this is because I have a short waist, and longer legs - I usually like a 30-32-inch inseam, depending on whether I am wearing flats or heels. I wear either ballet flats, or high heels - at least 3". Anything in between, and my feet look like water-skis (I have skinny ankles). For that reason, I don't wear peep-toe flats, because, again, I end up with a sort of boats-for-feet effect, that also makes me look much shorter.
I find boots to be tricksy - although I have (ahem) four or five pairs. I make sure they are very snugly fitted around the calf, and I generally only wear them with leggings, slim-fitted pants, or shorter skirts (mini or above-the-knee). With a longer skirt my legs look like they are the same width as my thighs/hips/waist. I get a weird column sort of effect.
I do have two pairs of OTK boots - one pair is flat, the other are high-heels, and I always get complimented on both. Short girls can definitely work these - but the key is that they have to fit snugly, and not pooch out or sag at the top. Otherwise, I end up looking like a ten-year old kid, playing dress-up in grown-up clothing.
As I write this, it occurs to me that boots, like anything else, rely on scale. If your boots are over-the-knee, or have heels, or are thicker material, you will want everything else you wear to be slim-fitted and lightweight and streamlined. If the boots are more delicate in appearance, then you can get away with chunkier knits.
littlebo
Demimondaine