You'll be surprised at how very easy it is for any guy to get dressed like this. Just a long sleeve henley shirt and blue jeans. When it comes to shoes, go for something on the casual end of the spectrum by rounding off with white high top sneakers. As the weather starts getting warmer, it's time to shed those heavy winter gear and choose an ensemble that's lighter, like this one here. Laid-back outfits for stylish 40-year-old men aren't actually that hard, as you can see.