Since some of you asked, let us examine the Case of the Terrible Tushie.
Our lovely lady shown in the photo has what we would call the Classic Pear Shape. She has a tiny, tiny waist and a more ample bottom. As one reader suggested, it may be that she has recently lost a considerable amount of weight, or it may be that she’s just comfy in her pants. Since she’s on her way to Martha’s Vineyard in the photos, she deserves no guff from me — she just happened to provide a perfect example of Frumpy Butt that I’ve seen on too many clergy in professional settings.
Let’s keep this simple:
When you buy or wear a skirt or pants, they should fit your thighs, tushie and waist. They should be a good length for you (a whole ‘nuther subject!). Regardez.

The fabric helps here, too. If you have a pear shape, do look for a touch of spandex in your trousers as it helps to shape the garment. Our lady in the photo is wearing an all-cotton pair; again, super comfy for vacation but don’t do at all for professional wear.

Good fit in the derriere and waist.

This is an excellent cut for gals with either a flatter, boysish figure or a chubby tummy situation: the waist is set a bit lower, which hugs the bum nicely and creates shape. This is PeaceBang’s preferred waist-line, since she has no real waist to speak of and a flat, wide rear (not to mention the complication of a generous inner tube around her lower abdomen). Pants cut any other way are just atrocious on me.
See, if you try to find pants that fit around a chubby waist, they will often be too roomy in the rear and thighs. If I tried to fit my “waist,” I would be drowning in fabric. Yes, I have some pants that fit like that that I wear around the house in the summer, but they’re called PAJAMAS or lounge wear.

See what I’m saying? We shouldn’t see fabric sagging around your thighs and rear. I cannot emphasize enough that fit makes all the difference in looking put together. Speaking as one who has a very “original” figure type,*I know it’s hard, and sometimes you make compromises. But if you attend to this issue, you will learn what works on you and beeline immediately for those garments in the future, saving yourself lots of time and heartache.
Example: I remember finding a beautiful sea-blue blazer at Macy’s about six years ago that wasn’t on sale, but was cut just perfectly for me: open collar, 3/4 length sleeves cut close to the arm, suggestion of a peplum at the waist (I SO need that definition there), three big buttons (small buttons on a big-busted girl don’t work), and made and lined so well that even my back looks smooth where it often is lumpy. I spent something like $85 on that blazer and I wear it ALL THE TIME. I never bit my nails once when I purchased it because I knew the moment I put it on that it would be my go-to jacket for thousands of “OMG, What Do I Wear?” occasions. 
Likewise for those two Dress Barn blazers that I bought on sale for $20 each several summers ago: I schlepped them home from New York City because they have a back half-belt (again, detail at the waist that I really need), big buttons, sleeves that fit, and are surprisingly well-made.
Pants are notoriously hard to shop for. Like I’m always saying, (1) do not settle for pants that don’t fit and (2) find a good tailor. Ignore trends like Skinny Jeans unless they work for you (and save real trendy stuff for days off and social situations).
NOW, let’s talk skirts for a moment.
A skirt should fit your waist, hips and thighs:

If you have a pear shape, skirts can be challenging. Please don’t be tempted to throw on a big, stiff A-line skirt and totally obliterate your shape. Find a skirt that fits your body and get the waist taken in.
Do check the front of the skirt for signs of pulling or creasing across the crotch area or thighs (if it does, do not buy it), and do make sure to sit and bend over in the skirt before you consider purchasing it. As usual, fabric makes all the difference. You don’t want anything clingy, but you want something with shape to it.
A caution: Long, flowing skirts can be gorgeous. However, long, flowing skirts that don’t fit just look dated and frumpy. The objective with a longer skirt should not just be, “Wow, I got it up over my waist! It fits!” Does it really? Or does it merely encase your body in fabric? If the latter, you will have to either have the skirt altered or learn some tricks to add shape to the garment (wearing fitted tunics over it, for instance, off-setting the bulk with great, chunky heels, pairing it with a shrunken blazer, layering accessories on top to balance the proportions, teasing your hair, etc.).

By the way, let’s keep these jaggedy hems out of the ministerial closet, shall we? Wear one to your friend’s wedding if you like or to your 50th birthday salsa dancing party, just not to professional events of any kind, not even in basic black:

Now go have a fit!!
* euphemism for roly-poly lady with all kinds of fascinating bumps and lumps.

“original†figure type, aka “traditional build,” as per _The No. 1 Ladies’ Detective Agency_ series by Alexander McCall Smith.
Thanks for the detailed explanation, with photos…I think I understand!
I think I understand, too. Fit = close to the actual contours of your actual body.
My personal issue is pear shape plus lump leg so I have tended to go for looser because otherwise, just ick. My salvation has been Not Your Daughters Jeans (http://www.notyourdaughtersjeans.com/index.php) which gives a fitted look without making me look at myself and go ick.
Any other thoughts for Thigh Baggage Issues?
For thigh baggage issues, look for fabrics that have a little weight to them. This is probably at least partly why you like those “Not Your Daughter’s Jeans”! Anything thin will tend to show every little lump and bump. Spandex, as PB mentions, is good not only for adding shape but also for adding a little heft to fabrics.
Also – the waistline that PB refers to here in this post is frequently called mid-rise or low-rise or “just below the waist”. Many times trouser labels are marked with the kind of waist fit they are and this makes it easier to you to figure out what to try on. Generally, fit descriptions like “At the waist”, “Classic fit” (which also tends to mean a tapered leg – ack!) and High waist are not flattering unless you have a very long torso.
I hear that, Gina. I’m short-backed, relatively speaking, and pear shaped. Thus my waist is always drowned in fabric in trousers that fit at the leg and hips but not the waist, or can’t actually get on trousers that would fit at the waist as they won’t go over my legs. And those thin trousers make me look…well, it’s just not pretty. Nor elegant, nor work appropriate!
And nobody looks good in tapered leg trousers. I mean, they just seem to be designed to make you look short and wide. I would swear LEGGINGS are more flattering, for crying out loud.
@ The Exegesis Fairy – try New York & Company for trousers – many of their cuts have a generous leg opening with a well-fitted waist, perfect for a pear shape. Reasonable prices too! Plus their jeans are great – very stylish!
And please remind the gentlemen that as we gain weight at the belly, the waist size increases and the contour and position change, the inseam size decreases. If you learned the expression “measure twice, cut once” in shop class, then this is similar.
PS Check out the Make Your Own Jeans web site.
Good rec, Gina, but I’m one of those Brits who is happily addicted to BTFM. So it’s off to Marks and Spencer for me, I’m afraid!
WBJ: Yes. Gents: Try. Things. On. If you don’t like shop changing rooms, do it as soon as you get home. Returny if no fitty, gottit?
Actually, no, scratch that: I’m far too lazy to work up the energy to return stuff that doesn’t fit, and if desperate might even wear it.
Try it on. In the shop. 😛
One thing I notice among my peers (I am in my late 20’s) is that BUY THE SIZE THAT FITS! No one but you and the person checking you out will ever see the size you are buying (cut out the tag if it really bothers you). Things that actually fit look so much more professional and also make you look SMALLER. No one looks thin or professional in pants that are pulling or a shirt that is obviously too short.
*and just in case you are wondering, I promise that the salesperson doesn’t care what size you are buying. Trust me. I speak from experience*
Happy shopping!