For a relaxed casual getup, dress in a black crew-neck t-shirt and navy jeans — these two pieces work really well together. A pair of navy and white suede low top sneakers will be the ideal complement for this ensemble. Mastering transitional fashion is easy with style inspiration like this. This ensemble is most probably what you've been looking for as a gentleman in his fifties.
For an outfit that's very simple but can be modified in a multitude of different ways, team a black crew-neck t-shirt with navy jeans. Introduce white leather high top sneakers to this outfit to bring a dash of stylish effortlessness to your outfit. This combo is super comfortable and will help you out in transitional weather. A fail-safe option outfit appropriate for 50-year-old men who prefer casual dressing.