Firstly, clothing sizes. This is a really grey area - I'm often a medium, but sometimes clothing lines which only specify 'small, medium or large' are really quite dodgy and I end up a small.
The only thing you can really do is a) find a shop which sells these things and check there or b) if you're buying online, check the returns policy on the website. If in doubt, and the site won't let you return things, find a friend or a seamstress (or even yourself, if you know how) to take the item in for you.
The dresses and skirts question is equally tricky as despite being pear-shaped myself, I find some things suit me very well, and a different skirt in the same style but from a different shop looks terrible. As a general rule, stay away from anything that rides too low on the hips, go for a wide waistband and make sure it FITS. The last one is an absolute must, because no matter how many people tell you something will suit you, if it's a size too small, or the zip sticks out, or the waistband won't lie flat you will look terrible.
Your best bet to find out what suits YOU is to go shopping with an honest and well-dressed friend and just try on everything you like the look of.
You are not alone at all. So, what to wear if you are a 'pear'? Trousers or skirts that emphasize your well defined waist area (softly pleated or flat-fronted). Try hipster trousers, as these will eliminate that gaping waist problem common to all pear shaped women. A-line skirts/wraps are by far the most flattering for 'pears' as they slim the hips and emphasize the smaller waist area. Short, tight skirts should be avoided as these will accentuate the tops of your thighs, and divert attention to that problematic area below the waist
Avoid light colored bottoms and stick to darker blues and browns which absorb the light
Tops should be fitted and focus the eye to your upper body (beautiful necklines, patterns and colors). They should not be baggy as these will cover your waist, and instead should finish at the top of your hips so that your waist is emphasized
Choose accessories (jeweler and scarves) that avert attention upward away from the hips and thighs.
If you're in the majority you will be a classic British pear shape (carrying most your stored fat around the thigh, hip, and bottom area). Rest assured that you are not the only one who gets frustrated when trying on a pair of jeans that gape around the waist area and can barely squeeze past your hips and thighs. Given that 70% of British women fall in to this category it is surprising that manufacturers of jeans still haven't cottoned on to the idea of making a well fitting pair of jeans for pear shaped women.
However in the mean time your best bet is to head straight for the clothing rail labeled 'hipsters'. Hipsters are great in avoiding the gaping waist scenario we all hate, as they sit on your hips not the waist.
Any pair of jeans with a low-cut waistband will make your bottom look smaller. Make sure the jeans are boot-cut, as these styles will balance out heavier hips and thighs. Jeans should be dark - steer away from light colors and paler 'washed look' jeans as these will do you no favors. Finally don't be tempted by denims containing stretchy materials such as Lycra as although these may seem more comfortable they will accentuate your problem areas below the waist by clinging to hips and thighs. Follow these guidelines and we think you will find your 'pear-fact' pair of jeans!