Dressing for the Man in His 50s 

The Advantages of Age: Personalize Your Look Over Time

Older men, on the other hand, enjoy a solid starting baseline: they've  got a good twenty or thirty years of accumulated clothes to work with. Get some of the old clothes back into rotation, with a trip to the  tailor for adjustments if you need them. 

Items Every Man in His 50s Should Own

A certain level of refinement goes well with gray hairs — and there are a  few classic items worth having in your wardrobe no matter what your  personal style leans toward.  Blazer jackets, Sports jackets, Fitted sweaters, Gray slacks, Wool overcoats, Dapper hats, Wristwatches

Dressing for Specific Occasions

Not all men need a business suit for work. These days, the majority  doesn’t, although the percentage of middle-aged men who need one is  higher than the percentage of younger men. As you rise in the ranks, a  higher dress standard is only natural.

Business Attire

Dressing for Specific Occasions

Now that we've covered the highest standard, let's look at what most  men end up wearing to work these days: the broad, nebulous category  known as “business casual.” 

Business Casual

Dressing for Specific Occasions

The more dressed-down and sloppy you look,  the more younger people are going to think “depressed retiree.” Stay  clear of work-out clothes and gym shoes, and sharpen up your look with  some non-work dress clothes:

Daytime Errands

Dressing for Specific Occasions

How dressy you look in the evening depends a lot on where you're going. Broadly speaking, be thinking darker colors rather than light, suits and  blazers rather than sports jackets, and open collars rather than  neckties unless you're somewhere very formal.

Evenings Out