The gents on the forum have excellent advice, especially for stretching your money. As a younger guy here's my take on casual fashion. Pick a golf shirt, or a t-shirt (generally large logo's make the best statement) and a set of high top hiking boots. Couple that with a nice wide belt and you can take or leave the sporran. It's a great outfit for the bars and the girls (of all ages) love to try and see if you're going "regimental," so expect to get pinched at least. For a younger guy, if you are not balding early wearing a hat makes you look like you are trying too hard or are a dork. Trust me I used to love hats too but finally gave them up and am better off for it. It's an easy look that lets you go lots of different ways and doesn't cost much. But dear lord stay away from the jacobite shirt unless you're going to Renfest and then it's up to the statement you want to make.