First off, I agree with the guys here telling you that you might be able to use this girl as a pivot, some proof into her social circle. If your goal is to simply befriend her, you'll have to kill your crush on her and game her as a way to become friends so you can meet her friends.
If you do that, don't come off as a tool. Act confident, aloof, cool, friendly. Joke a little, keep it light, etc. But even then, you'll probably have to drop a sexual joke or vibe here or there so that she'll feel you are a sexual, confident guy she can introduce to her friends.
Second, if you want to give it a shot at gaming her to get into her pants, there are some things you might try.
* You are going to lead the interaction. That is, you pick the day and time and you drive. Pick her up at her place.
* Stop somewhere unexpected first. Say, drop in a coffee shop and get a to go order. Know what you are going to order before you go in. Also, it might be a good idea to visit the shop first and get to know the people that work there in a first-name basis. Befriend them and use their name when you drop by with the girl you are gaming. You pay for yourself. If she wants coffee, that's up to her. It's not a date, don't treat it like one.
* Think of her as your bratty kid sister. Bust her chops here and there, but not too hard. Act like you don't take some things she says seriously. Think of almost everything she says as a sh!t-test, and agree and amplify. If you do this too often, you'll be a jerk, the bad kind. Do it just enough and you'll raise your status to or above hers. The point here is that since it was her offer to dress you better, she's entering the interaction more valued than you. You gotta get that leveled or even reversed.
* DO NOT at any point, apologize for your lack of clothing style. Act a little skeptical that you need anything changed. "Okay missy, since you know everything about clothing and evidently I do not, here's your chance to prove it to me."
* Make her work for the things she picks out. Don't like the first several things. In fact, that would be a good time to bust her chops, "REALLY? I'm mean, c'mon, dorks, IT specialists, and peeping toms where crap like that." ****y-funny, amused mastery. Make her prove to you she knows what she's doing.
* Also, get some compliance going. For instance, you are going to check out some shoes. Tell her to go over to the shirts and pick out 4 or 5 and bring them back to you and you'll try them on.
* Go to more than one place. This will create a time distortion and a sense of adventure.
* Make sure to try on some stuff that is way over your budget but that looks great and masculine. This will give her a chance to see you in a new light.
* If she picks out something you really don't like (and this might be a way of her testing you), you say, "The only way I'm trying that on is if you try on some of that lingerie over there first." Say this sort of sarcastically, funny, but derisively. It's not an insult, it's more, "your not very good at this, are you?" with a sexual twist thrown in.
* While at racks looking at shirts, this will be a good time to break slightly into her body space. Hold up a shirt in front of you, arm half-stretched, you stand behind her, your right shoulder up gently against her left, "What do you think?" She needs to get used to some kino early in the interaction. A little later as you move to one part of the store to another, gently put your hand on her lower back very briefly as you turn a corner or change areas. You are a team.
* At some point when you have something new on, stand about 5 feet from her and ask her how it looks. Look her straight in the eye and don't break contact. It should look a little like you are checking her out. Make sure your posture is good (hands on hips should work here).
* Don't let her demand you walking up and down the aisle with something new like you are a model there for her approval. Don't be her dancing monkey.
* When you find something she has picked that you really like and want to buy, say, "Hmmmm, I don't know. Not sure if I should trust you. If this looks like crap, we're never talking again."
* When you are finished shopping, go get a bite to eat. Take one of the bags into where you go and hit the bathroom. Change into a whole new outfit. Top to bottom. When you return to where she's seated, you'll look like a whole new person. She might even see you that way too.
* You'll make sure to get a table where you have an ability to sit next to her rather than across. When you return to the table, stand in front of her for a second, let her check out her work, and then sit down next to her.
* Now, get her talking about herself, not you. Make statements, not questions. Girls love talking about themselves and as the first part of the day was about your clothing style, you need to make this time about her. If she starts telling you all sorts of stories about her past, her likes, etc. You are doing good. Ask questions about her passions, dreams, goals, etc. Not factual crap like "where did you grow up", etc.
* If she starts asking you similar questions, she's interested. Keep your angle about only 1/4 towards her at first. Don't be overbearing with attention. Make her earn it
* If she sits to face you square, you are doing very well. Turn a bit more toward her, make good eye contact. See if her eyes are dilated. If they are, she's definitely into it.
* If she looks at your eyes, then your mouth, and then your eyes again, she's thinking about what it would be like to kiss you. Lean in confidently and give her a short but hot kiss. If she doesn't do that, you might still be doing okay.
* Now you bounce. Walking out the door, again you open the door and walking through place your hand on the bottom of her back and you guide her through.
* Open her car door. Drive her home. Walk her to her door. If she's talking and having fun, you are going to say, "This was fun. Thanks, I enjoyed it. Hey, there's a band playing (or something) Friday night and I was going to go. You should come with me." If she says yes, now you kiss her good-bye and do it well. Step into her space, your hand around her waist, look her in the eye and kiss her with confidence. Done and done.
All of this is irrelevant if she's a AW. Just notice the tenor of the interaction at each step and calibrate to what she's giving you.
It may not be a lost cause and she may be interested. But you'll have to lead the interaction and take responsibility for moving things along.
It snowed hard here yesterday. Evidently, I don't have much to do this afternoon than write up long missives to strangers on the internet.
Good luck
