For a casually dapper getup, wear a red windbreaker and black jeans — these two items go perfectly well together. A pair of grey suede low top sneakers rounds off this look quite well. When it comes to dressing for unpredictable fall weather, nothing beats a killer getup that can take you from season to season. This combo proves that moving from your 20s to your 30s is no reason to stop dressing casually.