Reach for a navy henley shirt and sports shorts if you're after a look option that speaks relaxed casual dapperness. For shoes, you can follow the classic route with a pair of dark brown desert boots. So as you can see, it's very easy to look dapper and stay warm when cooler weather arrives, thanks to this ensemble. This outfit is a huge inspiration to anyone who was hesitant about comfort dressing in his thirties.
For an ensemble that's super easy but can be worn in a myriad of different ways, consider wearing a grey vertical striped short sleeve shirt and sports shorts. You can get a little creative with shoes and polish up this outfit with a pair of dark brown desert boots. A knockout summer-to-fall ensemble like this one makes it extremely easy to welcome the new season. Casual getups for 30-something gents aren't actually that hard, as you can see.
This casual street style combo of a blue chambray long sleeve shirt and sports shorts can take on different forms depending on the way you style it. A pair of dark brown desert boots will add elegance to an otherwise simple ensemble. You can bet this combination is the answer to all of your transitional dressing problems. Wondering how to master casual outfits as you step into your 30s? This combo is a wonderful example.