Tailoring, tailoring-tailoring. Take the best suit money can buy, and leave off good tailoring and it'll hang on your body like a cheap suit. Buy a suit at Target and have it finely tailored ...
... and it'll look fantastic. It won't wear or dryclean great, but it'll fit you like a champ. I'm from the old school of suit wearing, allow me to impart my sage advice. ;)
1. Find a good local tailor, have 'em measure you. (Moosajees or Ambassador on Zamzama)
2. Try on a few suit coats with said measurement, make sure they hang about right. Same with slacks.
3. Cuffs are good - contrary to belief they're never "out", and they have a functional advantage, they make slacks hang just right. They keep the pant legs from hanging getting caught in your shoes as well.
4. Dryclean the suit coat and the slacks at the same time. If you wear the suit on Saturday, get some gunk on the slacks, do NOT have just the slacks only cleaned. Even the best suit can fade a teeny tad with a cleaning, so keep the wear/fading even - clean both at the same time. (Do not send to cheap dry cleaners. Send it a nice hotel's dry cleaning outfit)
5. A suit that's not stained does NOT need to be drycleaned after each wearing, or each 5 wearings. Your under garments take on the body oil and stink, its not a worry, a suit will last years longer if not over cleaned. (wear a blood sleeved vest)
6. Wear a t shirt - it looks better. Period.
7. Make sure your tie meets the middle of your belt, please, please, oh please.
8. Show some cuff. Have your tailor cut the suit coat so your Properly long dress shirt shows just a bit. It looks sharp, and adds contrast to between your suit and hand.
9. Don't forget the dress shirt, 100% cotton ONLY, get them professionally laundered, and get a dry cleaner who knows what heavy starch means. Ya, I know, it sounds like it'll be "itchy", but after wearing the shirt for about 15 minutes its no more "itchy" than light starch. Ahh, the look of a crisp starched shirt. You'll have people ask you how your shirts look so crisp and sharp.
10. Traveling? Your dry cleaner has you covered. Instead of having your shirts on hangers as per usual, request they fold the shirts. They'll fold them, use some cardboard like a brand new shirt to save the collar from pressing down, and package it all up in a plastic bag - again just like a new shirt. That shirt is ready to travel!
11. Wrinkles? Well just hang your suit up. 100% wool will hang out nicely. Tough wrinkles? Travelling? Hang the suit in the bathroom when you shower, the steam will let the wrinkles release. And, if you have an otherwise clean suit have your drycleaner give it a press before that special event, it just costs a few bucks and your suit will look like it was just cleaned. Never have a suit that doesn't need a cleaning put therugh the rigors of dry-cleaning.
There. 20 years of wearing a suit 5 days a week imparted in 4 minutes.