1969 Mens Fashions via JC Penny's

Season 7, more so than any other season, I see Janie Bryant really taking some risks with the mens costumes, especially with characters like Harry and Stan, who have already shown during Season 6 that they are moving along with the times, wearing more of the up-to-date trends while many of the other man slowly eased into the end of the decade.

I'm really pulling for one last shot of Pete in shorts -- maybe in a pair like G (yellow and green floral print) above -- allowing his character to come full circle fashion-wise.

    

As you can see from the press release above, it seems that Bryant is sticking with the tight tapered leg pants that have really dominated the series.  And while this look is prominent in the JC Penny's catalog, I am hoping that the closer the season gets to 1970, the wider the mens pants legs get. 

 Roger is really one of the only "older" men on the show that is pushing outside the normal limits of his character this season and has possibly come the furthest (fashion-wise) from Season 1 (although a just as good argument can be made for Harry as well).  It looks as though he could trade places with the JC Penny's model on the left, demonstrating his ability to keep up with the times.  Roger's transformation seems the most fitting between the lead men on the show.  Whereas Don is classic, I see Roger as being more trendy, especially after his relationship with Jane.  I predict Roger being one of the firsts to exhibit flared bottom pants.

Where do you see the men of Mad Men going this season?