Crew-neck T-shirt with Derby Shoes Smart Casual Fall Outfits After 50

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Black Sunglasses Dark Brown Beaded Bracelet Silver Watch Black Crew-neck T-shirt Black Chinos Black Shirt Jacket Black Leather Derby Shoes

This pairing of a crew-neck t-shirt and black chinos is indisputable proof that a pared down off-duty outfit doesn't have to be boring. Let your sartorial sensibilities truly shine by completing this getup with a pair of derby shoes. A stylish summer-to-fall transition getup like this one makes it very easy to embrace the new season. This pairing illustrates that dressing stylishly as a mature man is easier than one might think.

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Black Sunglasses Black and White Polka Dot Scarf Burgundy Blazer White and Black Horizontal Striped Cardigan White Crew-neck T-shirt Charcoal Leather Belt Grey Wool Dress Pants Burgundy Leather Derby Shoes

Teaming a crew-neck t-shirt and grey wool dress pants is a surefire way to breathe personality into your styling repertoire. For something more on the elegant end to finish off this look, introduce a pair of derby shoes to the mix. As you can see, this look is a really great pick, especially for unpredictable fall weather, when the temperatures are dropping. This ensemble demonstrates that figuring out how to dress stylishly at 50 and beyond is not that daunting a task.

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Black Sunglasses Beige Crew-neck T-shirt Camel Overcoat Black Leather Derby Shoes Black Tie-Dye Chinos

A crew-neck t-shirt and black tie-dye chinos are among those super versatile menswear items that can refresh your wardrobe. To give this outfit a sleeker touch, why not go for derby shoes? So as you can see, this look is a really wonderful idea, especially for transitional weather, when the mercury is getting lower. How's that for fashion inspiration for dressing in your 50s?

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White Crew-neck T-shirt Olive Long Sleeve Shirt Silver Watch Light Blue Cardigan Light Blue Jeans Dark Green Socks Brown Leather Derby Shoes

A crew-neck t-shirt and light blue jeans paired together are a match made in heaven for gents who appreciate casual styles. Play down the casualness of your outfit by finishing off with derby shoes. Seeing as temperatures are starting to drop, this ensemble is a viable idea for the transitional season. Dressed like this, any older gentleman is bound to put most 20-somethings to shame.

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Navy Baseball Cap Clear Sunglasses Grey Crew-neck T-shirt Navy Shirt Jacket Blue Jeans Dark Brown Leather Derby Shoes

This off-duty combo of a crew-neck t-shirt and blue jeans comes in useful when you need to look cool and casual but have zero time. Rounding off with derby shoes is a guaranteed way to infuse a hint of sophistication into your getup. So when summer is over and fall is setting in, you'll find this look to be your everything. A safe bet ensemble appropriate for 50-something gentlemen.