Stick to the classics and don't be afraid to buy used. eBay and thrift stores in wealthy areas are your friends. If you're embarrassed, then buy anyway and don't tell anyone. You can pick up thousands of dollars of clothes for a couple hundred. Stay with the classics because they don't go out of fashion. Plain white shirts will always be around. Also, you won't be ashamed to show photos of yourself to your children in 2029.
Pick up an iron and ironing board. Ironing isn't difficult and you'll knock it off fast once you get used to it.
For basic wear, pick up plain white, collared, long sleeved dress shirts. Don't bother with crests, monograms, or decoration, just get plain white shirts. They go with everything and have been appropriate for decades.
Speaking of logos, I avoid them as much as possible. I'll even take tags off clothing. You can cut the stitching with a knife, then pull out the threads with tweezers. Rubbing the cloth will cause the holes to disappear. If you look at the very top end of clothing, you'll notice few, if any, logos. If there are any, they're tiny. So if you get chinos from Target (or wherever) take the tags off for an instant upgrade.
If you want to get a few more shirts, a few plain blue ones are good. Maybe even a conservative blue and white striped one. Don't go for anything loud or trendy. Avoid weird collars.
For pants, you need at least a few pairs of khaki chinos. Get plain fronted (no pleats) and a straight leg is a safe bet. Get a slim cut if you can pull it off. 100% cotton is best. Buy a little too long and find a tailor to take them up just right for you. It's not expensive and it's worth it. You'll look better, and even a pair of $20 pants will look good if they're the right length. You can also DIY this if you have access to a sewing machine and do your homework on alterations.
For dress pants, again, go conservative. Wool is best and look for dark browns, blues, greys, and black. Tan is good, too. Avoid patterns and pleats.
Pick up at least two belts, one brown and one black. Wear one that matches your shoes. Get the simplest, plainest belts available with the plainest buckles. Get full grain leather, if possible. Split grain doesn't hold up.
Get two good pairs of shoes, one brown and the other black. The safest bet is a plain toed Oxford. Captoes and wingtips are OK, too. Leather soled shoes are best. They hold up for years and you can have them resoled for a lifetime. I've had one pair of black wingtips for 18 years - they've been resoled and still look great. Shoes are expensive, but cheap on eBay. My trick is to measure a shoe that fits well and then buy a shoe with the same dimensions on eBay. It's worked every time. Some good brands to look for used are Alden, vintage Florsheim (the new stuff isn't as good), Brooks Bros., Barker, Cheaney, Loake, Peal, Edward Green, Church's, Lobb, and probably a few others I'm forgetting. For more casual shoes, a pair of tan suede bucks always look good, as does a pair of classic boat shoes, like those from Bass or Sperry.
For suits, pick plain, basic ones in navy or charcoal. I like Brooks Bros. and Hickey Freeman suits. Both are classic American and are well made. Don't get double breasted unless you're over 6' tall. Single breasted, two button jackets, without shoulder pads and a single vent are classic and look good on everyone. If you go for used, don't worry about a perfect fit. You can always buy a little big and have it tailored.
Get a wool topcoat (plain and dark colors) if you live somewhere cold. A tan, plain trenchcoat is good, too.
If you need ties, get conservative silk ones with stripes or small patterns. Learn to tie a proper Windsor (full or half) instead of the four-in-hand. A Windsor looks better and shows you take the tie seriously.
If you shop sales and hunt used clothes, you should be able to put together the basics on the cheap. Don't be afraid of the tailor, either. If you get conservative, well made, used clothes, then have them taken to your size, you'll look great and everyone will think you spent a fortune. Get to know your tailor, as well, and ask for advice on what you should buy and where. Don't think you need to stand out from everyone, either. A plain white shirt and a pair of tan chinos is totally classic and you'll look great now or ten years from now.
