I'm over 40 and about your height. I am not a fashion plate, but I dress pretty well in my idiom. I don't like fussing and can get out the door in 10 minutes from stepping out of the shower, so this is all low maintenance.

Jeans are fine. Make sure the jeans have a bit of tailoring to them; boot-cut jeans or trouser-style are flattering to a lot of women. If you want dress trousers, at your height I'd check out J Crew or go to a store where they will tailor.

I like jeans with blazers. Value Village sometimes has fun, funky blazers, but it's also worth watching sales. Natural materials wear and last better than synthetics.

Leather boots help give a more polished look. I think you're better off with one or two pairs of really good interesting shoes than more pairs of lower-quality shoes.

Plain T-shirts are a lot more flexible than ones with logos. If your T-shirts are long-sleeved, have you considered learning to wear scarves? They're a good way of getting some variety to a very basic wardrobe.

How's your hair? Is it a bit polished (or intentionally not polished), or does it need cutting? That's something else to watch.

Whatever you do, wear something fitted, especially if you're opting for blazers and dress shirts. I've gotten a lot of inspiration from the Sartorialist (http://thesartorialist.blogspot.com/) for women's fashion, and he really has an eye for men's fashion.

Here are some photos of his that I think are good examples of casual clothes dressed up and made more fashionable, or formal clothes dressed down to look more casual. You're better off going with one option or both in Seattle:

http://www.thesartorialist.com/photos/61610BohoCouple_2218Web.jpg

http://www.thesartorialist.com/photos/MVcardigan_4374Web.jpg

http://www.thesartorialist.com/photos/72010AndiJordan_8047Web.jpg

http://www.thesartorialist.com/photos/62410Suited_6019Web.jpg

http://www.thesartorialist.com/photos/41410Paint_4838Web.jpg

(For the record, I assumed you were a dude from the size you specified.)

Think fit. Any outfit will be elevated from "shlub" to "OK" or even stylish with good tailoring. Silhouette is important; for men, defined shoulders and waist. Remember, fit isn't "tight"; it's a silhouette that's comfortable, skims your body, and flatters.

Keep to straight trousers (very classic) and stay away from relaxed cargoes; they make you look young and the weight of stuff in the pockets makes your pants look sloppy. Jeans are best dark and straight, as they can be dressed up and down. Ensure the pants are the right length.

Collared shirts are fantastic -- again, can be dressed up and down. Really flexible. Get white ones and print ones, and you'll be set. You can wear short-sleeve print in the summer or roll up the sleeves of lighter ones. You can layer with a sweater in the winter. Again - FIT. I really love how Italian shirts are carefully darted in the back, which eliminates that awful billowing that can happen with men's shirts.

You're already aware you're not quite dressing the way you'd like; start researching what you do want to look like. Look at other men (that was pretty much my strategy when trying to change the way I dress).

Bring those ideas when you go shopping. If you're unsure about specific styles, you can start by asking for help in a good department store or menswear store; they do this for a living so don't feel self-conscious about it. Tell them what kind of workplace environment, social environment, style you're aiming for, and they can help you experiment.

(There are also plenty of men's fashion blogs online; I really enjoy reading Put This On.)

Opt for dark wash bootcut jeans and get them long enough. A lot of designer jeans are super long or stores like American Eagle have really great extra tall jeans online (believe me, their slim boot style looks good on every body type I've ever seen).

Pair the jeans with nice tunic tops (make sure they're not too big, just loose enough to be comfy but basically fitted) for a good, flattering look on most women. Or pair those tunic tops with leggings, which I also think look good on most body sizes (just make sure the tops cover your butt).

Grab some nice printed jersey dresses. Wrap dresses are particularly flattering to most women. You can find inexpensive ones at places like Target and Old Navy.

Another way to dress up your look is shoes. Get a pair of cute ballet flats and some knee high boots. Ballet flats are a good dressy alternative to heels and flat soled knee high boots allow you to wear skirts and dresses year round (with tights) while still being comfortable.

You can find a lot of what you'll need at thrift stores (try the Crown Hill Value Village), Target, H&M, Old Navy and the like.

Regarding Thailand and custom suits: there's a place called Manhattan Custom Tailor in the (seedy) Sukhumvit district of Bangkok that I've seen beautiful, clean work from. They're pretty well established, I've seen recent fits and 10+ year old suits that still look great. Be VERY wary of the avalanche of tailoring offers you will get; seek out your own work, look at the pieces they have on display to get an idea of quality, and get several fittings!

1. Watch back episodes of 'what not to wear' and get used to ascerbic retorts from stylists.

2. use most of your budget to hire a stylist. take notes, and as time passes, use what you've learned to build a wardrobe over time rather than have a 'makeover spree'.

3. do not assume that today's advice will be good for a decade.

4. iron things, avoid tee shirts with stripes, and tuck things in.