This look demonstrates that it is totally worth investing in such timeless menswear pieces as a brown three piece suit and a dress shirt. When not sure about what to wear when it comes to footwear, go with burgundy leather dress boots. When leaves turn yellow and red and fall takes over, you'll love this look as your favorite for unpredictable fall weather. So if you're searching for a good-looking but also age-appropriate outfit, this just might be it.