1. Be patient. It is harder looking fashionable as a heavier guy but it's not impossible. Patience is essential to have. 2. Most of your shopping is going to be done online. Know your measurements. Know your shoulder width, neck size, chest size, true waist size, torso length, the size where you actually wear your pants, inseam, outseam, shoe size, the works. 3. Be wary of brick and mortar stores. Know which brands and find the brands that cater best to your weight. Some brands specialize in certain cuts and patterns; know what works and know what doesn't. 4. Worry about your fit first and foremost. Consider what kind of style suits you next. Fit is the single most important factor in looking presentable. 5. Don't worry about "Oh, I'm going to lose weight so I might as not buy that". Looking good goes a long way in building confidence to lose weight. A lot of articles of clothing can be altered by a tailor, so make sure you befriend a good one. 6. Don't do baggy clothes. Baggy clothes makes you look even heavier than you actually look. Of course, buttons shouldn't be popping out all over the place and your clothing shouldn't be strained, but make sure it fits right. 7. Get a made to measure suit on the cheap. It'll fit better, and you can always get it altered. If money is a bit of an issue, make sure the off the rack jacket fits in the shoulders, and opt for a two button or three button. 8. Try and shy away from shorts. It's not a very flattering look most of the time. 9. NEVER EVER EVER wear workout clothes in public. They make you look lazy, 10. Vertical lines and dark colors. They are your new best friends.