Wait! They do? How do I hook myself up with one of those?

Can I just go in and say "I'm traveling. I need a couple of casual, coordinated outfits that will pack well and stand up to a day of airports, airline seats and active walks through the city." and walk out with a couple of reasonable ensembles? Because that sounds like a very pleasant fantasy world.

I hate the act of shopping. I don't mind spending money. I don't mind trying on clothes. I'm willing to wear clothes that take me out of my comfort zone. But actually going into stores and trying to guess how things are cut, and gathering up 42 different pairs of pants, only to discover that they-all- gape at the waist... It's so much less appealing than cleaning my bathrooms again.

At Nordstrom? Yes. Macy's? Probably. I don't know about LB, but it seems that there'd be a lot less to select from there.

You're looking for a personal shopper.

Remember that regardless of how great the stuff she pulls for you is, you'll still need to try on and so some selecting among the choices. It's painless but not totally effortless.

I highly suggest Youtube for Make up tutorials.
You can search whatever look you like!

Here is my routine:

I use a tinted moisturizer with sunscreen in it. (Aveeno or Dr Jarts Beauty Balm which is water based) Or sometimes I use a face primer.

A thin layer of light loose powder to reduce shine

I highlight the cheek bones and under eyes with a Luminizer

Some eyeshadow primer

A eyeliner of a pretty flattering color used in a thick line, then I use a eyeshadow brush and smudge it gently over the eyelid for a nice hint of color on the lid.

A black (or other basic color coordinated color) eye liner in a thin line across the top of the lashes to give the eye definition.

Finish off with some lip gloss.

This is the look that has gotten me the most compliments. It's simple, natural with just a hint of smolder in the eyes. Takes about 10 minutes for me to complete. Lasts all day long and I just reapply the gloss as needed.

it works well for my jeans and t-shirt style. My Hair is 99% of the time in a ponytail.

Hey, another geek here and I'm pretty sure I wrote a pretty similar post to yours about a year ago! For me I actually started blogging a bit about things that I've gone through to well, find well-fitting clothes and try to get at least some fashion sense. The good part, though, is that when you have zero-fashion sense you can only go up from there!

First things first. GET A GOOD BRA AND UNDERWEAR. No T-shirts are going to look good on you if you don't have a good bra, I'm just saying. This should be #1. Make sure your band size is correct (band size=ribcage measurement) and that your cups are big enough and supportive. I just can't emphasize this enough regardless of your size.

You mention gapping at the waist for pants, so I'm guessing your have a larger butt/thighs. If so check out pants with Curve (Levi's Curve ID jeans, PZI, Little in the Middle etc). Those might help you out a lot. Also taking the pants in in the back is a pretty simple alteration that you might even be able to do yourself.

Like others said understand your body type. I'm a big fan of focusing on your good points and bad points. Many body types are pretty overgeneralized so honestly look at your body, what parts do you what to show off, what parts do you want to hide? Then research each body part to find out what will help (or post here and just ask ).

Another thing... This might be just me but since we're in the process of losing weight and like me you probably work with a bunch of guys who are not up on the latest fashion trends then I really go for well-fitting stables. I don't have very many pieces of clothes that fit at the moment but when I find something I like I get it altered so it looks great vs. buying more clothes that don't fit as well. I know it's not always cheap but I'd rather wash clothes more often and have well-fitting clothes because it really makes you look more put together.

As for a certain style. I don't really have anything at the moment. I LOVE the vintage look but I don't dare invest in any nice dresses due to the cost so instead I pretty much have jeans/slacks and shirts. It works for now and once I hit goal I'll definitely change things more. Oh, and definitely check out used clothing stores, especially since you like a bargain. Then you can toy around more with different styles and you won't have to spend a ton.

I suck at make-up and can't really even wear much of it at all due to skin allergies so I'll leave that for everyone else.

I grew up in the same manor. Plus being over weight for so long, I'm a jeans, sneakers, (men's) T-shirt kind of girl. And I only wear make once or twice a month. Special occasions really.
Going shopping scares me! lol
I don'r know how old you are (I'm 30) but I wouldn't recomeend that What Not to Wear either only because they dress everyone so uncomfortable and old. I've seen girls in their 20s on there and when they are done with them, they're dressd like 3 decades older. And the cost! I can not take fashion advice from someone that will spend $500 on a pair of shoes! Besides, those outfits, IMO, aren't real worl clothes. They remind me of the runway models, or a slightly tamed Lady Gaga.
I would suggest people watching. That's what I did. I make a point to nocite what other girls are wearing. Do I like it? what does it highlight and what does it play down? Real people like at the mall, let me see a lot of different styles on different bodies and in motion. I started to see what kind of styles I liked, and which I didn't, and made a mental note for shopping trips.

I gathered myself up today and went to the mall. I discovered that I really do need to wear petite tops, even though I'm long-waisted.

And that Coldwater Creek, even if I like some of their things, thinks I have a much larger waist than I do. I was looking for a wide black belt to extend my waistline up a little (so my legs don't look so short), and even a small was loose. I don't know what was up with that. I found things I liked the style of, but not the color and things I liked the color, but not the style... but it's progress.

I went to the Macy's to look for some jeans, because a pair of jeans that -fits- would get a lot of wear in my life. However, I don't have the patience to sort through 7 different racks of jeans per designer looking for a pair in the style and size I need. For $120 per pair, I expect them to at least be sorted by style, if not size.

After that, I'd had way, way too much shopping, but I'll venture out again soon.

I didn't see anyone who had responded to this point, but if you go to any sort of salon and say you'd like your eyebrows shaped up, they'll do it for you! You don't need to know any specifics (although you can always say thicker or thinner or whatever) and they'll take it from there!

Good luck!

I would also suggest looking at Polyvore. People have put together complete outfits so you can pick a set you like and find it in your area.

Also, try smaller stores like Ann Taylor Loft where you may be able to get help with jeans.

I wanted to say that I like What Not to Wear. Even if the outfits aren't everyone's tastes, they do teach good basic. Dark Wash jeans that aren't too long, fitting your body now, jackets that pull in at the waist, not "loosey goosey" shirts if you have a stomach, finding the right length skirt for your legs, etc. I think if you take the basics of what they say you can find a great style.

Start simple first. Wear nice form fitting t shirts and tanks with form fitting jeans and pants. Forever 21 is very affordable and it has every single style that you can imagine. Everything there is fashionable and comfortable so you'll always be in style. For tips look at magazines and search up fashion pics online. It's easier to start out small and gradually start to build you fashion style once you've found what you like.

For your eye brows just go to the salon and ask them to do your eyebrows. Tel her to clean them for you that way it isn't too drastic. Once it's done you'll see how different you look and then you can decide whether or not you want to shape them or leave them like that. You'll probably need to re-do them every 2 weeks.

Photos, photos, photos.

I always try on clothes in the dressing room and snap a quick picture from my camera. It's a great way to see the whole package. After my shopping trip, I'll review the pictures and see which pieces look amazing on me.

Magazines are a great way to start too! It's important to know your body shape and what flatters. I am a pear shape so there are certain styles I can't wear because it makes me look pregnant. I also know I have broad shoulders so complicated sleeves make me look top heavy.

It's also important to note that just because you don't look good in it, doesn't mean something is wrong with you. There will be things you can pull off and rock it better than anyone else just keep looking!

Shopping is one of the tools I use to stay motivated

ive always been a metalhead and i thought the smaller i got the more risque id dress and i do sometimes like i love corsets, fishnets, see through stuff, but i still wear my old tattered jeans and band shirts and dog collar 75% of the time. its just who i am no matter my size. im never gonna be the girl in a dress so tiny it doesn't cover her bits and 7 inch stilettos, im gonna be in the patched up jeans with my guitar but i mean thats me and you have to find out who you are regardless of your size and wear clothes at your goal weight that expresses your indivuality, youll probably find clues to your style in your big clothes, like go through it and whatever pieces you liked most will hold clues to what you like, if you didnt like any of your old clothes or your husbands then just go to the mall and browse and see what sparks your interest the most, dont go for whatever you think is fashionable or whats 'proper' go where your fashionheart wants to go

I'm in basically the same boat, and what has helped me a TON is shopping with a friend with a slightly better sense of style than myself. We'll go a store, I'll pick out the two or three things that I like on the hanger, and she'll pick out about a million more that I've agreed to try on without complaining. Bonus points if the friend has a chance to see what you already have in your closet before you go.