White and Blue Dress Shirt with Chelsea Boots Dressy Cold Weather Outfits For Men After 50

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White Dress Shirt Black and White Horizontal Striped Tie White Pocket Square Black Overcoat Black Double Breasted Blazer Dark Brown Leather Briefcase Blue Wool Dress Pants Dark Brown Suede Chelsea Boots

Try teaming a white and blue dress shirt with blue wool dress pants and you're bound to turn every head in the room. Finishing with a pair of chelsea boots is an effective way to infuse a more laid-back finish into this look. So if you're looking for outfit ideas on what to wear as you get into your 50s, this pairing is a perfect example.