There is a saying in fashion that it is better to be overdressed than underdressed. I am 90% casual so in order to upgrade my look I select a long sleeve shirt or sweater and wear dress shoes or boots. These changes totally affect the image because I am also very comfortable with either option.
I tend to wear jeans all the time. I have a lighter , straight leg pair that are my weekend running around Jean. But I have a bunch of dark and black jeans that are the staple of wardrobe. Last summer I added a couple of cotton, chino type pants that feel like jeans ( Old Navy ) to the closet in order to expand the palate. But the whole look depends on my shirts and shoes.
The same jeans with a Henley shirt ( my go to, and next article ) and Vans slip on, have a total different look when I wear a fitted polo shirt and loafers. But I can take my girlfriend out with a nice pressed long sleeve white shirt, a shot of cologne ( do it ! ) and my dress boots with those same jeans.
The key is to be as flexible as you can with what you already have. If you can mix and match items you can create many looks with the same articles. The shoes, which must be cleaned every time you wear them are the factoring point of whether a look works or doesn’t. A scuffed, muddy untied shoe drags the eyes down and kills the image you just created.
Be The Man 