For boys today there are few occasions that require a radical change of dress compared to everyday wear.
There is underwear, which may consist of boxers, Y-fronts, slip-ons or boy shorts. Until adolescence when there may be greater need for modesty or support, most boys will be happy to wear whatever has been purchased for them and is comfortable to wear. Labels may be a nuisance but they can easily be cut out, seams might be irritating so next time choose a different style or a seamless pair of underpants; trial and error will determine the style your boy is most comfortable with though they may still insist (while they are quite young) on the latest cartoon film character regardless of the comfort they may or may not bring to the wearer. Fabrics for underwear are various although cotton mixes are the most popular. It's best to avoid nylon pants as they generate heat and cause excessive sweating. Vests or T-shirts might be worn as undergarments on chilly days and rather than wearing pajamas per se, your boy might opt for a pair of boxers and a tee as his night attire. Whether you're going to school, out to play or to a party it probably does not matter what underwear you have on as long as it is clean and comfortable.
Outer wear probably consists of school uniform and non-school clothes. If your boy needs to attend a dressy function like a wedding it would probably be more worthy to hire an outfit than to make a purchase that would only be worn once. For functions such aserals and formal occasions a smart pair of slacks and a button down shirt with a tie (optional or indeed borrowed) would suffice. If your boy has a formal school uniform you can use the trousers and shirt from it to make up an outfit. What makes an outfit classy or trashy is the footwear with which it is worn so make sure you child does have a pair of respectable looking shoes other than trainers / sandals / boots that are clean and polished to pull off an air of respectability.
Jeans, shorts / boardies, cargo pants and track pants are comfortable and interchangeable with a variety of different tops to see your boy through everyday. A bank of classic plain T-shirts will go with any of the trousers and a hoody or sweat top should suffice for the rough and tumble of an active childhood. A favorite T-shirt, football top or rugby shirt is practical to wear and as long as it is not wrecked with rips, stains or grubby wear marks is perfectly acceptable in most situations. Beyond these basics is a personal choice that suits your budget, wardrobe and storage space and the world is your oyster. Outfits do not have to be painstakingly co-ordinated with matching accessories, that detracts from the individual's personality and self-expression so make allowances for personal taste and preferences when helping your boy choose clothing that he will like to wear and you are willing to pay for.