Trash my closet and start over? I don't know how to dress myself.

Hm. I'm going to go against the grain a little here. Sounds to me like you're not that interested in clothes, and you're also discriminating and minimalist. (I say that because you say garish patterns irritate you, you don't want to look either young or old, and you don't own jewelry.) Given that, I don't think a personal shopper or reading a lot of blogs is going to help you much. Personal shoppers *like* clothes, and are into fashion -- they can dress you up once, but you won't learn anything, and I'm guessing you'll find it boring and frustrating. They're also fundamentally sales people: their interests aren't the same as yours. Essentially the same thing is true for fashion blogs. They are written by people who love playing with clothes, and you are not one of those people. I think you should focus on building a wardrobe of basics, slowly over time. Buy less, and buy better quality. If I were you, I'd go somewhere like Bloomingdale's or Neiman Marcus, and take a look at brands like Theory, T by Alexander Wang, maybe Michael Stars, Velvet, and Rag and Bone. That's more money than you're used to paying, but the upside is it takes out a lot of the guesswork. Fabric and cut will be better than cheap brands, there will be less extraneous foofery, and the clothes will feel better on your body, hang better and last longer. Maybe also try quality "active" brands like Icebreaker and Smartwool. If you do that for a while, I'm guessing eventually you'll start to figure out what you like, and what suits you.

Just for what it's worth--your impression that "clothes are made for curves" is pretty inaccurate. In fact, most clothing is made to look good on models, mannequins, and hangers, none of which are notable for their big boobs or curvy hips.

I went through this process in the two years. I actually just put together some links to things that I found wildly helpful http://whitneytheorycrafts.com/2014/01/12/helpful-links-for-transitioning-from-wearing-clothes-to-having-a-style/.

If you have some real money to throw at this, I would consider signing up for a personal shopper/stylist session at a department store. I know Nordstrom's has this kind of service, but I am sure others do as well. Go once, and learn mightily! Another idea: select a http://www.puttingmetogether.com/2013/01/wardrobe-from-scratch-part-2-choosing.html you like and buy stuff in that palette only. It sounds limiting, but it's actually quite freeing because when you shop, you don't get bogged down in the sheer quantity of stuff. You look for things that are your colors, and then mixing and matching gets easier as well. Personally, I've recently treated myself to a monthly delivery service called https://stitchfix.com/. With $20/month and a decently completed profile, they send me 5 items I can try on and keep or return as needed. There is a time-limit, so you have to return things quickly, but the $20 goes towards anything you decide to keep. I L-O-V-E this, because I dislike shopping in stores and using dressing rooms, and so far, I am a believer in their stylists. It's been a LOT of fun. But individual pieces are closer to $75 than $25 in general. Prices in my suggestions above are going to be hard for you to adjust to, I think, and that's understandable. However, buying nice pieces for more money has made me feel way more put together and keeps my wardrobe reasonable/manageable, so I'm not overwhelmed when I dress each day. And the items last longer, too.

1. Shave legs 2. Buy some skirts 3. Get some boots I am telling you, skirts+boots = cuuuuuuuute!! It looks like you put a lot of effort into dressing, when all you did was roll out of bed and put a skirt on.

I'm somewhat in your same boat in terms of personal (lack of) style, disliking shopping, and not really knowing what I want to wear in general. I also primarily do freelance work from home so have no real incentive to look good on a daily basis. However, I had a realization the other day that I could up my style game significantly (to me, at least) by making just a couple of easy, incremental changes. Here's what I currently wear (basically exactly what you currently wear albeit maybe one step up) and how I'm swapping: 1. dark-blue skinny Gap jeans: keeping these 2. various short- and long-sleeved Gap t-shirts: keeping these (for now) 3. various colors of Roots hoodies: swapping these out for long hooded http://www1.macys.com/shop/product/ideology-long-sleeve-hooded-wrap-cardigan?ID=1140316 4. adding a http://www.target.com/p/oversized-city-lights-scarf-blue/-/A-14938773#prodSlot=medium_1_30&term=scarf: these can be found cheap and everywhere 5. adidas sneakers: swapping these out for http://www.zappos.com/frye-smith-engineer-short-tan-pebbled-antique and/or http://www.zappos.com/frye-veronica-slouch-black-vintage-tumbled-full-grain boots Upgrading in stages is seeming way more manageable to me than going for a complete overhaul all at once.

Step 1 that worked for me is discarding (donating) EVERYTHING with stains, frays, and holes. This includes underwear. If throwing stuff out upsets you, you can put the non-donatable things into textile recycling. You have to tell yourself: if you had it in you to mend the hole properly, wouldn't you have done it by now? Step 1 is easy because it's a binary choice: is there, or is there not, a hole? If you have a friend to strengthen you in this, now's the time to ply him/her with refreshments in exchange for help. Step 2 is almost completed, but I still have some holdouts. Donate EVERYTHING you dislike. Even if your mother or late grandmother gave it to you, even if you bought it at a particular store in your old hometown, even if OTHER PEOPLE like it on you, even if it was a good deal... After this you should have, let's say, 3 days' worth of clothing about which you feel neutral. Maybe even 1 or 2 positives. Step 3 is to get new stuff at an affordable price...I'm not there yet.

You are tall (taller than 5'9"?), and relatively slim you say? well there's a place for you: Jcrew. (they do tall sizing through the internets and it's magnificent) don't like being preppy? take a look at Madewell or Gap. Jeans wise, I love Levi's- and they run closer to $60 for a new pair of pants and have a sizing system that kind of does make sense. now how to approach this..... first spend 1 day emptying your closet of anything ripped, stained or very unflattering. (you know that shirt you won't even wear on laundry day, but keep just in case? yea get rid of it). also get rid of any single socks, and weird uncomfy underwear. then.... I would start with switching out your hoodie to a blazer and getting a new pair of jeans. This lets you keep your old t-shirts/current uniform but slowly upgrades it. In the spring, buy a pair of flats. now you're wearing newish jeans, a blazer, comfy old t-shirt and niceish shoes. In the summer, try on a necklace, and flip your t-shirt to a tank top. still got your (now) old jeans, blazer (if it's cold), tank top, but working in some jewelry. and in fall, back to t-shirt, blazer, jeans, keep the flats and then switch out the necklace for a scarf. refresh your jeans. maybe get a few new t-shirts.

Dressing is a skill you can learn systematically. You might find that a lot of things in your current wardrobe are just fine, if you combine them right. Follow me: Measure your bust, the circumference of your shoulders, your waist, and your hips. That will give you an idea of relative proportions. It's late now so I can't get to the exact formulas, but it sounds like you kind of have a grasp on the horizontal proportions already. But if you are sufficiently motivated, MeMail me. Measure the length of your head, from the top of your head to your chin. Now measure your full height. Divide your full height by your head length. Measure your leg length from the soles of your feet to your crotch. Divide by your head length. If your legs are more than 4 head lengths long, you have long legs. If they are less than 4 head lengths long, you have short legs. Bang on 4 head lengths, and your legs are proportionate. Measure your rise length, which is your natural waist down to your crotch. If your rise is more than 1 head length long, you have a long rise. Less, and you have a short rise. 1 head length and your rise is proportionate. Measure from your natural waist to your chin. This is your waist length. A proportionate waist is 3 head lengths long. More, you are longwaisted, and less, you are shortwaisted. Now, get a copy of Trinny & Susannah's "The Rules". Take a look at each body detail (big bust/no bust, etc.) Now look at your measurements to see whether a category applies to you. Try to take the emotion out of it and focus on the numbers. If you get stuck, MeMail me. Supposing it turns out that you have a big bust. Take an item out of your closet. There are clothes that are recommended for busty women and clothes that are anti-recommended. Try to work out whether the garment you're looking at is recommended or anti-recommended. Remember, just focus on the bust for now. Over time, you will build up a complete picture. Once you've decided whether that garment is supposed to look bad or good on you (shape-wise, you can move on to colour later), put it on and wear it for a day. If it's bad, well presumably you've been wearing it up to now, so you won't end up looking worse than you already have been. But, while you're wearing it, try to take in your observations about it and get a feel for why it's bad or why it's good. At the end of the day, write that garment down on a list, check a column Y/N as to its suitability, and make notes if you want to. The next day, take out another garment and do the same. Do this for a few days, then move on to the next feature (like "no waist" or something). People complain that this system is confusing because a style is recommended for one feature that they have, but anti-recommended for another feature that they have. The answer is that a garment that is "bad" in any category should be ruled out. What's left will be the good garments that fit both features. After some time, you will have really taken in the idea of what shapes look good on you and what shapes don't, and you will have done this using your own wardrobe; you haven't bought anything yet. Now let's consider colour. I have to say, I'm not nuts about all this colour-analysis business. Here's what you do. Take a pile of clothes and stand in good daylight. Hold a garment up to your chin. The garments that make you look younger and smoother and brighter are in good colours for you. The ones that make you look more crumpled and haggard are in bad colours for you. If something's in a bad colour, you can still wear it, but keep it away from your face - save that colour for skirts and pants, etc. If, after a while, you are feeling hopelessly lumpy and as if nothing you can do is ever going to help, you are probably suffering from Bad Underwear. Bikini panties will give you quadributt; thongs will give you Cellulite On Parade. For example. If either of those things apply, shorts are recommended. I realise this probably goes against your nature but if you really want to start building on the best foundations (har), you should see if you have a branch of Rigby & Peller anywhere within travelling distance and book a consultation with them. Their underwear is so expensive... but to be honest, from what you've said, I think you can afford it. And if you do this once... you will know into the future what underwear fits you best, and which styles to shop for at a much lower price point. Think about it. And after you master that, we can move on to the really advanced stuff. Your adventure awaits you.