I LOVE suiting up! It just makes me feel more manly and sharp and I even act differently. We used to have nights out with my friends where we went to different places in suits. Places that don't usually have suited people.
Now with that being said most people from my experience that don't like wearing suits have had a bad experience with one. It looks bad, cheap, doesn't fit right, is a very outdated style or they might not fit in with their peers.
I can't tell you how many people look bad in suits that don't have to and yes the sneaker thing is just bad bad bad.
Now lets go over how to fix this.
1. A suit doesn't have to be stuffy or boring but it should be classic and fit right. I recommend an actual store that sell suits. Men's warehouse is a great place! They have people that can actually fit you into a good suit and they will show you a ton of different styles to let you choose what you like. Stay away from super modern styles and go with something you can wear for a while. Most suits are not very expensive (even Italian ones) and can last for years. STAY AWAY FROM PLACES THAT SELL SEPARATES! Get a coat and jacket that are made together.
2. The shirt and tie make the suit. They are as important as the suit it self and you need to spend good money on thick ties not something that you get at sears or jc penny. They will last forever and make you look like a real man. Make sure the shirt and tie are not tight and they should fit and flow with your body style. Custom made shirts can be expensive but buy quality! How can you tell quality? Hold the shirt up tot he light, if you can see through it it won't last. Dry clean then with heavy starch twice then move to light. The heavy twice rule is to make sure they get a good base coat like paining. Stay away from bright colors with shirts and it you want some flair go with a bright tie that's not very cluttered. STAY AWAY FROM BRAND TIES (Tabasco, Disney, logo's or thin width ties.
3. Shoes! Don't go cheap here. JUST DON'T DO IT. Don't buy them at a place like walmart or some shoe barn place. Go have them fitted with a thick, leather sole. No rubber souls! They should have some depth and height to them. Go with black for darker suits and a nice light brown for summer or spring suits!
4. With these few element you can make a ton of things look good! Use the jacket with a nice button down shirt, good jeans and your shoes for a nice casual dinner or night out (not to fancy, not to causal). Make your suit part of your look! It can define you!
5. Make sure you dress for your size and shape. If your a big and tall man make sure your stuff fits. If you pack on the noodles for the holidays, take your suit to a tailor and for as little as 25-30 bucks you can have them alter it and still look sharp. Stay away from thin ties and form fitting jackets. They look good on a model but not a real man.
If your a shorter man use longer accents (suit store people will show you), go with a bow tie (tie yourself) and long lines. You can also get shoes that can make you almost 2" taller (and no not those weird lift style shoes) with the larger heals on shoes now a days.
I love dressing up, for anything! I don't have a legit SUIT right now, just some nice dress clothes, but I'll still wear those out once in a while just to look nice. Honestly, I have no clue why a guy wouldn't like to dress up, girls love it, and I just like the feel of it.
I have no problem with wearing a suit. I have a couple myself. Though appearance wise, I like uniforms better and I think I'd prefer wearing something like an officers uniform rather than a suit in the situations that call for dressing like such.
Suits suck, ties suck, sh*t even dress shirts suck. If I lived in a place where the weather was cooler I'd have less of an issue with it, but it's brutal in hot humid weather. Ties in general are uncomfortable. When you're a tall man 6'3" with broad shoulders and long arms it's almost impossible to find dress shirts that actually fit in regular stores. You have to search high and low and pay 3 times what other men do or get everything custom tailored. It's not encouraging. =P I dress in a suit when I go to a formal event and will slip on a dress shirt and a tie when I have a business proposal to pitch, but I wouldn't say it's something I like to do.
I like dressing up. Normally I'm a t-shirt and jeans guy but when an important event is up like a wedding or any formal event nothing looks cooler and better than a dark colored designer suit and shiny black polished shoes.