Like many people, I have waaaaay too many clothes and don't wear a lot of them. Part of this is that I just like clothes too much, but part of it is that I'm very hard to fit. I'd buy something that didn't quite fit, often because I needed it and couldn't find anything better, and then end up not wearing it much because it didn't fit quite right. Then I'd buy another something that didn't fit quite right in a different way. Or I'd buy something that looked ok at first, but after a day's wear didn't. The things that I bought that did turn out to fit right would get worn to death, but I wouldn't even know why.

I've become interested in sewing and part of that is learning how to fit patterns. I was stunned to realize that most of the clothes I own simply don't fit right and never did. The best thing about learning to sew has been learning how to fit ready-to-wear. (Note that unless you're a size/shape that is really hard to fit in ready-to-wear, you won't save a dime sewing for yourself. Alterations are cost effective, but sewing garments is an expensive hobby. There are tariffs on textiles, but not on clothes made in sweatshops.)

When I first discovered this, I bought some fairly expensive clothes, but they fit. The difference in comfort and look was amazing. Once I got used to how a correct fit looked and felt, I could go back to the consignment shops and thrift stores. Now I buy a lot fewer clothes that I like better and are more comfortable. They look more professional. It's also easier to say "no" to not-quite-right-but-cheap clothes, because I know what's wrong with them.

Everyone's individual fit is different, and learning how to see if something fits takes practice. Some general points: Learn to tell if it fits in the shoulders, because that's easy to get wrong and kind of weird to figure out if it's right or not -- shoulders are often "off." There's no one rule of thumb because there are lots of different styles for garment shoulders, and each has its own way to look right. They're also very difficult to have altered to be right. Make sure the lengths (sleeves, pants, hems, etc.) are good and the neckline/collar doesn't gap -- those are easier to fix. I learned fitting from pattern alteration books, but I'll bet the nice salespeople at expensive clothing stores can help. When you get more advanced, you can look for where darts point, the pitch of sleeves in suit jackets, and other minutia.

The first step for any woman is to make sure your bra fits. If your bra doesn't fit, your shirts can't, and most women are wearing bras that don't fit (which are also varying degrees of uncomfortable). If your bra hurts at all, it doesn't fit. In my experience, Nordstrom has awesome fitters and a good selection of clearance bras. Victoria's Secret, Macy's, and other places simply aren't as good, because they don't have the size range that Nordstrom does -- it's hard to figure out your size if it's not in the store. The measuring system you're supposed to use to figure out bra fit is wrong for most people, giving you too high a band size and too low a cup size (a direct route to shoulder pain). It does work for some people, but not many; I custom-make bras, so I'm not just being contrary here.

I don't have equivalent advice for men, but I have a lot of male friends who hate wearing suits (and often consequently underdress for their jobs). When I see them dressed up, they're invariably in a suit that doesn't fit -- of course they hate dressing up!

I can't speak for other guys but I buy my clothes off the rack, and they fit. I sometimes don't even bother to try them on before buying.

My aversion to wearing a suit has nothing to do with the fit and everything to do with the noose around my neck. Take away the tie and undo the top button and I'm perfectly comfortable.

That is because your shirt does not fit.

I have a huge problem finding clothes that fit off the rack. The most comfortable clothes I own are my custom tailored suits and shirts... but I can't afford to wear those everyday and my work environment doesn't call for it.

Just finding a pair of jeans is next to impossible. At 5'8" and 175lbs in good shape (almost a six pack) I am neither a bodybuilder nor a fat ass... yet nothing fits. Nothing more frustrating then spending all day at a mall trying on clothes and leaving with nothing.

My day to day wardrobe consists of 2 pairs of jeans and a bunch of t-shirts that don't quite fit right. I also have a few golf shirts I wear, they are a bit long, baggy around the middle and a bit too tight across the chest and shoulders but oh well. I'm not rich enough to get everything custom tailored.

Bingo!!! I wore snug clothes with a tie and hated it then I started purchasing shirts that fit. Now, I love wearing a tie. Also, I love the reaction my co-workers have seeing me in nice clothing.

You're saying that if my shirt fit better, I wouldn't mind having a tie around my neck? I hope you're just being glib, because otherwise that's painfully dumb.

As a 5'10" woman (ok, girl, whatever), I have the hardest time with pants. They seem to be my sworn enemy. I can usually find jeans offered in longer inseams, but dress pants? Nope. Not that I mind wearing skirts when I dress up, but they're also a problem too, as shorter skirts seem a LOT shorter on my long legs. I'd like to have some nicer clothes, but my height and my budget has restricted me to "jeans and t-shirt girl."

It's also hard to find shirts that are long enough - sure, showing my midriff is cool while I'm still 20, but as I get older, it's only going to get more annoying (ps, I hate showing my midriff, but it's fairly socially acceptable given my age, so I don't worry about it too much).

The implication is that if your shirt fit better at the collar (i.e. was not as tight) wearing a tie would be more comfortable. This could easily be true and you won't know unless you try it.

True for me. You will not feel a constricting feeling around your neck when you have a correctly sized shirt and a nice tie. I wear suites daily when I am in school and thus gravitate toward my correctly fitted attire.

Why?

Seriously. Why is it dumb to think a tie wouldn't be uncomfortable? I know a lot of people who wear them without a problem.

Being able to get into clothes doesn't necessarily mean that they fit. Almost by definition, something that is uncomfortable doesn't fit properly. Exceptions are inappropriate fabric (itchy, too hot, etc.) or style (parkas in midsummer).

Having a skirt hemmed doesn't cost that much; you might try getting longer skirts (which I would guess would land on the wrong part of your leg to look good) and have them hemmed to a length that works. Doing it yourself is pretty cheap, since all you need is one of those ancient straight-stitch sewing machines you can get free or cheap at a garage sale. Another possibility is ordering online, since they're more likely to have ranges of sizes. My favorite trick is to try on expensive clothes in the store, then order the ones I know fit.