Denim Shirts For City Boys

nov 06 2014

In my last post, I talked about how Walt Longmire’s sense of self should be something you should emulate in your style. But I got some questions about how to take things in a more literal direction: denim.

I’ll never outright condone wearing denim on denim . I think it looks as boring as any monochromatic nonsense. However, adding a denim shirt to your mix of workwear can make any Wednesday (or Tuesday or Friday) a bit more fun.

The quick and dirty version of how to wear a denim shirt is as follows: If you would wear a light blue, wear the denim and see how it looks (very business pro and formal occasions aside, of course). Like it? Good, now you’re dressed. Go to work.

If you need some inspiration, check out these fine lads over on (
I like to wear my chambray with a textured navy tie, tie bar, belt, and khaki cords. I throw on some brown shoes (and some suspenders if I’m feeling fancy) and I’m out the door and headed down town.  For shoe inspriration, check out this neat little pic.  I love contrasting laces!  It really ties the whole outfit together.

For rocking it with a blazer, follow this guide to be sure that you have a look for every season.

These are what makes a denim shirted outfit really shine


It’s funny. I really love this combo (maybe that’s why I wrote about Walt). It feels modern without being unapproachable. And I get compliments every time I wear it. Ladies love that my style gets so “out of the box” and guys dig how easy and uncomplicated it is.

Believe the hype about layering with sweaters too.  It’s effortless modern cool.  The modern gentleman’s take on the old time working man.

Overall, I give the denim shirt 10/10. Would definitely recommend.


I’ll leave you with one final bit of inspiration to take with you:

This guy’s look is worth imitating.

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