A few tips on dressing up little men:
1. Keep it simple and slightly hipster.
this striped one, from The Children's Place. At $7.95, it is the perfect little boy accessory. This gray tie [similar here] is actually a real tie I bought last year. My husband tied the full Windsor and then we slip it over his head. Pair the tie with a white shirt and pair of jeans-you are good to go.
2. Forgo the dress shoes. Buy something they will wear again.
3. Improvise if they grow out of something.
The arms of the white shirt from last year were too short on my big guy. I didn't want to buy new. The rest of the shirt fit great, so I improvised. We rolled up the sleeves and he looked casually cool.
Rest assured. If you are mother to boys, you can still play dress up!