A big part of being Milfy and Maintaining a Degree of Fuckability is how you dress for the part. This is not about size, this is about knowing how to dress for your size and your particular shape. Over at You Look Fab, Angie has put together what she calls "The Flop Proof Outfit". You can read about it here. You can also refer to this outfit as the "What Not to Wear" casual outfit.
Now I know it's kind of boring, but hell, you can't break the rules unless you know them first. Not everyone can strut it like me in a pair of knee-high silver Doc Martens and a skirt the size of a dinner napkin. This will come later. I myself have spent many years dressing as if I were several sizes larger, but after faking the confidence for a while, eventually I found that I actually had it for real. (Now if I could just tone the ego down slightly, I think I'd have it going on.)
So the first thing, The Jeans. Mom jeans. You know you've seen them. High-waisted, saggy assed, pleated, acid washed, tapered leg, hell, even gunty. *gasp* Yes. Gunty! Just generally ill-fitting and ugly. Get rid of them! Don't even give them to Goodwill, cut them up into tiny pieces so that no one will be able to wear them EVER AGAIN. I'm not against recycling, I'm just against bad fashion.
Get some that fit well, and the darker the better. This might take you years! Once you find a pair of jeans that fit you perfectly, stock up on them! It's not as if they ever go out of style. You don't have to go for the skinnies if you think they make you look like a bowling pin, but the thing is, we never look as big as we think we are. (And they fit great into your boots!) Take a girlfriend or your best gay with you, someone who can be honest and who will tell you if you look awful. Try on many different styles, even if you think you hate them. Also, if you have the problem that I have with the waist band gaping at the back because you actually have an ass, it's okay to get that shit tailored. You will wear them more if you don't have to keep hiking them up from exposing your butt crack. Just say no to crack, but don't hike them up under your tits, either.
Okay, so next is the shirt. On You Look Fab it says "shirt or girly top". Fuck that. Titty top. You want to show off what you've got. If you're worried about stray motor-boaters, then wear a camisole underneath for some coverage. But I'm telling you, let those girls out to play once in a while. You don't have to push them up under your chin like Jessica Simpson, but live a little.
Jacket. This means "tailored jacket". Something that has a shape. You can find a combat-jacket that nips in at the waist if that's your style. Your options are unlimited. There are blazers, motorcycle jackets, leather, pleather, even a cardigan if you live in Mr. Rogers' neighbourhood, which I do. ;)
Heels. Yes. Heels. Again, you don't have to go all porny with the shoes if you don't feel comfortable that way. Stilettos are better, but if you like those little coloured ballet flats feel free to wear them if you're worried about bunions. And don't just get black! Have fun with the shoes. Try some boots, even.
Statement bag. I fail miserably at this. The statement that my bag makes is that I'm a Mom and I have to carry everyone else's shit around. This is not the ideal. You don't have to match it with the shoes, but for Buddha's sake don't use the same one until it falls apart. I keep all of my stuff in little wallets, change purses or tiny make-up bags so that when I need to switch purses everything is easy to switch over.
Let us say that you're like me and have a problem with authority. You want to break the rules! Break one at a time. See how it works for you, and if it does, break a few more! Add some accessories! Play with colours and fabrics! But most of all, have fun. Strut. Say, "I am Milfy, hear me roar!" *rawr*; and let yourself believe it.