I really, really, really, really need an edit function, badly. By “fingertip length” I meant the length of the shirt. Not the depth of the neckline! But that’s what it sounds like! Yarrrrr!
Well, if it’s a one time only thing, a big change can be kind of fun.
As far as the heels, if this is your first time, then bite the bullet and hit a good shoe store. You should find someone with the experience necessary to help you find your first pair. You may pay a bit more, but believe me, you’d pay more in the long run hitting a Payless and grabbing some random pair off the shelf.
Practice practice practice walking in them.
A piece of advice. Stockings and garter are sexy, but do not try wearing them in public if you aren’t used to them. I find them a pain the butt in real life (this led to me excussing myself to the ladies room during dinner for my boyfriend’s birthday to get the hell out of them).
For high heels, try something with a bit of a platform - I find it gives the shoe a bit more stability thus making me not quite so wobbly. And you don’t have to spend a fortune for a pair of shoes you’re going to wear infrequently at best. I have a really sexy black satin pair that always garners compiments and they cost me all of $19.99 at Shoe Carnival.
Surly
Who hates high heels with the white hot intensity of a thousand suns and only wears them on the most formal of formal occasions.
Shirts that long can be dicey when you’re hippy, though. Longer shirts and tunics end up making you (often) look more pear-shaped.
Seconded. Ivylass is giving some good advice, here.
IMHE, the best heels in the world come from stores that specialize in dance footwear. I have one pair of heels, and they came from a place that specializes in shoes for ballroom dancing. They’re the only genuinely comfortable heels I’ve ever worn. I paid about $100 for them, but they were well worth it.
You’ll ruin the soles of the shoes if you wear them outside, but you can have them re-soled.
I wouldn’t worry too much about the high heels (I wish other women would stop wearing them so shoe manufacturers would stop making those damned bunny-killers) - there are plenty of feminine, dressy shoes that you don’t have to learn to wear.
I think Hilarity is on the right track - I don’t think you need to turn yourself into a massive girly-girl to dress a little sexier and prettier. I am really lucky to have a husband who seems to understand women’s fashions better than I do - he gives me excellent advice on which clothes look good on me and which don’t (and , as far as I know, he’s not gay!). He usually steers me away from the oversized t-shirt and loose pants look - towards more fitted, feminine shirts and dressier pants or skirts. They’re still comfortable (I won’t wear uncomfortable clothes), but I look like a regular lady.
If you’re not comfortable wearing make-up or dolling up your hair, I would suggest practicing it at home by yourself until you get a look that you are pretty sure isn’t going to scare children. 
But, like others have said, make sure your husband actually cares about your hair and make-up before you go off the deep end. He might be a guy who prefers the au naturel look, and really doesn’t care about lipstick on you. I asked my husband what I could wear to look sexier around the house for him - turns out, his big turn-on is an unbuttoned pajama shirt, not something from Victoria’s Secret.
If you have the money for it, I’d suggest getting something you like tailored to your particular sense of style. I’m a wannabe seamstress, so I’ve made everything that I own that I consider sexy - and because I did all of the work on it, I know it fits me well, and I know it looks good on me - and when I know it, the Tashaboy knows it.
Like a lot of people have said, sexy is a state of mind. When we first started dating, I was very timid about him, because I’d had so many fucked up relationships in the past. Now I’m very assertive about our relationship, and about what I want, without being a bitch about what he wants. I’ve gained some weight but I still like myself and find myself attractive, and ergo, he does too.
About the weight loss thing - do you enjoy exercise? Because I hate it. But I’ve found a lot of physical activities that I enjoy - Dance Dance Revolution (lost 20 lbs in a month and a half with that sucker), hula classes (those are FUN! and very sensual, too - a primeval kind of sensual that Mouse_Spouse might even enjoy ^_~), things like that. If you find something physical that you like, you won’t think of it as exercise or a chore, and you’ll probably do it more often.
On the topic of what might look good on you - you’re very pale. Do you often wear light colors like white and pastels? If you do, you might want to go for a total switch, just to see how it looks - try some darker or vibrant colors, like black or red. And you do have very nice hair - mess around with it. One of my favorite things to do when the Tashaboy isn’t around is go into the bathroom and experiment with different hairstyles and makeup combinations. I don’t have a lot of time for it, but when I do it’s fun, and then I can wash it off with special face cleanser and call it pampering.
Best of luck - looking sexy ain’t easy, but it’s worth the results.
~Tasha
Find some lingerie that makes you feel sexy. Wear it under whatever cute little dress you decide to wear, and just the knowledge that you’re wearing it will make you feel more confident and sexier. Plus, it’s a nice surprise for your husband to find later.
Wear a little makeup. A bit of mascara and sheer lipstick can do wonders.
Heels are a bitch. My doctor has forbidden me to wear heels. Since I wear a size 5, it’s not a real problem, size 5 stilettos don’t exist 
but… can you find shoes with boot heels? They have those around here and you can almost walk normally. Almost. If your usual walk is, like mine, fitting for a Marine on parade, you’ll have to remember to bend your knees and step a bit less far
You have a very nice back and shoulders. If the dress has an open back (doesn’t have to be so low you need a special bra; any kind of dip will be more of a dip than you usually wear) and you wear a shawl then your back and shoulders will be playing peek-a-boo when you walk with the shawl on and be on display when you take it off.
Can you find a hairdresser who will understand “I’m allergic to gels”? My own hair is very fine and abundant, wavy but not curly; if I comb it too much it loses its natural wave. A couple times I’ve gone to a new place, informed them that I did NOT want any kind of gels and to please don’t pull too much when combing it and, at some point during the blow-drying, I heard a gasp when they realized that “oh! oh, my, your wair is wavy! I mean, by itself!” Well, yeah, it’s genetic and I know tons of women who pay a lot to try and convince half a wave to join their straight hair, so could you just Leave It Be?
Oh, I’m not supposed to be in the market for shoes! But now I am drooling over these…
I agree with the advice not to go too far out of your comfort range. But a classic black dress will be suitable for a number of occasions, or maybe a classic pair of dark trousers and your can change up the shirt. Again, with a pear-shape choose a shirt with wider-set shoulders (not shoulder pads, but a wider neckline at the top); it will balance out the wider lower half. And a nice open neckline focuses attention of your face (or so they say on What Not to Wear) and a pretty necklace if you so choose.
There are days when I enjoy going to the gym and days I would rather have teeth pulled. I like to hike and once there’s enough snow I’ll try snow-shoeing. I’ve taken belly dancing classes. That’s lots of fun, but I have a very poor sense of rhythm. (and very self-conscience.)
When Mouse_Spouse and I were dating, he commented on how often I wore grey. Over the years, I have bought more colorful clothes, usually blues and greens. (Its now a joke between us: Look honey! Its not grey!)
I had a great stylist, but he’s disappeared! 
Brooks where are you? From my experience, no one is happy with their hair.
Hey, my daughter is happy with her hair! But she’s only five. 
Post pictures when you get the new hairdo! And never let your best stylist leave. Track them down if you need to. Cindy at my salon moved to California and I’ve never forgiven her. :mad:
Well a “good friend” of mine is buying me a corset. Doesn’t look like you need one but a lot of guys like them anyway. Slightly painful, vaguely exotic. With stockings (NOT pantyhose) and possibly heels.
Beyond that I’d take the thought that you want to figure out your best bits and show them off. Nice tits? Good bra and low cut shirt. Great ass? Really good skirt. Nicely turned calf? Short skirt and great stockings (NOT pantyhose).
That’s too bad - you don’t, as I can see, have any real reasons to be self conscious. Then again, I’m not really the self-conscious type; I’ve always been very…uh, out there and confident about that kind of thing. I think this might be part of the reason you’re having issues; if you have to ask how to be sexy, you obviously don’t think you’re sexy enough. 
Too bad, because I’ve known women twice as ugly and twice as big as you, who were downright sexy - cuz they knew it. If it matters, I don’t think it would be that hard to make you physically sexy - it’s the mental thing, like everyone else has said, that takes overcoming. Best of luck.
[QUOTE=Mouse_Maven]
When Mouse_Spouse and I were dating, he commented on how often I wore grey. Over the years, I have bought more colorful clothes, usually blues and greens. (Its now a joke between us: Look honey! Its not grey!)
You know, the Tashaboy and I have this exact same conversation, except about black - because we’re both stagehands, ninety percent of our clothing is black slacks and black crew T-Shirts or polos or button-downs - but always black. I’ve thrown a little red in there recently (and, you know, my standard blue jeans) and it certainly startled the Tashaboy to find out that I’m not color-blind.
~Tasha
I’ve taken today off as a “mental health day”. All these suggestions are going with me to the local mall. We’ll see how things go. . . 
tashbot, you’re wonderful with the compliments. I’ve always had issues with my looks. shrug With every guy I dated, I made the first move. It bugs me. What? I’m not good-looking enough? Then there is all the “you look just like your mother - the ugly bitch” my father gave me. (Gotta love Father Dearest. :rolleyes: Then there was the occasional "You’re every guy’s worst nightmare: You’re not much to look at and you’re to smart for your own good.)
I think it’s time you stopped listening to your father.
Oh yeah. I haven’t spoken to him in over a decade. Amazing how that sort of stuff is hard to shake off. Years of therapy and whenever I feel down all the crap he said creeps back in.
You look fine to me. Sure, let’s not expect to see you walking down the catwalk anytime soon, but you’re just fine.
Like I’ve said - I’ve seen uglier women who I could call sexy. You’ve definitely got potential.
And obviously, Mouse_Spouse enjoys it, so you did something right.
Best of luck, seriously - and don’t lose being a tomboy, that’s what he fell in love with. 'sides, tomboys have more fun. flexes
~Tasha