13 Tips For Men: How (Not) To Dress For Casual Friday

Before I even start talking about what to wear on casual fridays, I’ll acknowledge that all offices are different, and most are getting more and more casual by the second.  So the term “casual friday” is a little outdated in some cases.  Granted.  And I do hate the idea of people telling other people what to wear, and I think rules for the sake of it are silly.  But I did want to take a moment to point out that while the objective of all of this rule relaxation is to reflect flattened organizational structures and an emphasis on innovation and to lure the young folk into the workplace, there is some potential danger to your career here if you aren’t just a bit careful.  You don’t want this to devolve into what you would wear sitting on your couch watching sports.  Or while working out.  The objective is to look cool and casual and feel comfortable.  Not to look like you might fall asleep with nachos on your chest or like you just finished a ten mile run.  

Here are some good rules of thumb:

1. Clean clothes only.  You still want people to believe that you have your act together in all areas of your life.  Among other things, this means you do your laundry.

2. You need to shower. One time I had to talk to an employee about body odor because people were complaining about him.  Mortifying for all involved.  

3. Undershirts are meant only for under.  Think of them like underwear.  Because they are.  

4. No sports jerseys.  Not everyone loves your team.  Some people hate them.  We don’t need them to hate you.  Also, jerseys are really only cool with deep context.  Wearing them to the office kind of looks like a costume. 

5. No gym attire.  Running shorts, sweatpants and spandex tops are revealing and just don’t seem to match with a workday persona.  And on a somewhat related note…

6. Definitely no tank tops.  I feel like it’s safe to say that your coworkers don’t want to see your armpit hair.  

Now for some ideas:

7. The uniform: you can still do casual dress pants and a button-down shirt.  You absolutely cannot go wrong here in terms of appropriateness.  Just make sure it all fits.  I know a site that can help…

8. Here’s a little secret to men’s style: layers.  Button-down shirt plus plus button-up cardigan plus casual blazer.  This reminds me of the Friends episode where Joey puts on all of Chandler’s clothes.  Which I now feel compelled to share:

9. Jeans are fine.  Just not with holes, rips or crack.  As in butt crack.  Or visible boxers.  Just generally keep your underneaths underneath.

10. Khakis.  Sure.  But again, fit.  Please don’t wear big old baggy ones with pleated fronts.  You are better than that.  

11. For tops - sweaters, short-sleeved sweaters, polos - all cool.  

12. I actually think shorts can be ok, depending on your work environment.  Just make sure they are to your knees and that they basically look like a shortened version of casual dress pants.  And consider a belt and tucking in your shirt to compensate a little.  Business on top, party on the bottom.  And by “party” I am only referring to bare calves.  


13. Shoes - dress shoes, loafers, all great.  Nice leather sandals might even be ok depending on your workplace, but never socks with sandals. (Special public service announcement about socks: please never wear white socks with dress shoes.  Thanks.)  Sneakers can look cool if they aren’t running shoes and if the rest of the look is somewhat dressy.  See below - with or without the jacket.  


And finally, some more inspiration: