Consider teaming a navy field jacket with dress pants to look like a perfect dandy. Make your look less formal by finishing with burgundy casual boots. This one is a viable choice when it comes to an amazing transition look. So if you're looking for fashion inspiration for dressing as you go into your 50s, this getup is perfect.
This elegant combo of a grey bomber jacket and dress pants will prove your styling skills. To give your ensemble a more relaxed touch, add a pair of burgundy casual boots to the mix. As you can see, it's super easy to look amazing and stay comfy when chillier weather arrives, all thanks to combos like this one. This combo is a good illustration 50-something gentlemen can still very well draw compliments.