Simon Crompton of Permanent Style recently did a post about baseball caps and logos (see here). I think the gist of his post was about authenticity and that ball caps can look good. He prefers a logo that means something to the wearer and doesn’t care for made up logos. I said something similar about ball caps and authenticity in 2016 (Are baseball caps trad?), but I don’t mind made up logos, no logos, or luxury caps. Why I am writing about this is that Simon’s post created a lot more controversy in a trad/ivy related sub-reddit that I follow (here) than I would have anticipated. Specifically the part about wearing a ballcap with tailoring. Some people like it, but people that don’t like it seem to really really hate it.
I will add my 2 cents on the subject. I don’t think of the ball cap and blazer look as anything new. I used to have a great floor to ceiling window in my old office which was located near a few banks, the courthouse, and some law offices. I have seen men downtown in blazers, sport coats, and suits put on a baseball hat when it’s windy, raining, or very sunny for well over a decade. Keep in mind this was in a smaller city. In Ohio. We are talking main street USA not LA, NYC, or London where Simon mentions that he has never seen the look. Maybe it’s newer that men are wearing ball caps not for weather protection, but for style or maybe it’s new that it’s featured in look books and advertising. I am not sure. I seem to recall a Muffy Aldrich or Ivy Style blog post about men in NYC wearing ball caps with blazers 7-10 years ago, but I couldn’t find it. I have a more open opinion than many it seems. I think like most things it can look good or it can look bad. It just depends.
I leave you with a few pics. The first is man that I spotted on the street about 4 years ago. He was a wearing a 3/2 roll patch pocket blazer, p3 type glasses, OCBD, foulard tie, khakis, tassels, and a tan baseball hat. I thought that he looked cool so I snapped a pic. He reminded me of the men that I described above. An old school guy throwing on a ball cap outside of his office (probably to protect his head from the sun). I highly doubt that this guy reads about menswear trends online. The other two pics are of me. I am wearing a hat in one pic because it was rainy and in the other because it was very windy. My down vest will probably cause as much pushback as the cap, but I like it. I thought that the cap looked pretty good too. Hence the pic. The hat is from a golf course that I played in case you were wondering.
For more hat related content here is a link to my post: Horrible Protestant Hats By P.J. O’ROURKE
Hey Jerrod, nice post.
I have done the low profile unstructed dad cap (baseball cap) and blazer or tweed sports coat in the past. It helps if it’s done with chinos as opposed to jeans. It looks good when done in an Ivy Style, but not necessarily a Neo Ivy or Neo Prep style.
Personally I have an issue with Simon Crompton. He promotes anti-Sartorialism far too often and it’s ruined his credibility. He also just writes fluff pieces to make money of google ads and affiliate links.
Case and point, have a look at the way Simon wears an OCBD shirt. He wouldn’t know the first thing about a Brooks Brothers OCBD, in fact I would wager he’s never even owned one.
Simon is too much mate, lets keep him in the dog house.
Thanks, Tie Clip. It seems you have a good handle on how to make it work for you which is more than half the battle. I am not that familiar with Simon, but your take is interesting. When I glanced at his blog I thought it was probably high end for me.
This reminds me of the downside of the fall of the grand fedora. There is no standard headwear to wear with tailoring like our grandfathers enjoyed. Nearly any hat—beanie, ball cap, flat cap—in many/most cases look odd with tailoring. This is highly impractical, because as you say, weather is a reality whether or not you are wearing a suit and men need some kind of headwear to handle that. Somehow society found a way to make any headwear worn with tailoring seem odd! (Including the fedora, which has a heavy stigma)
Miami Trad, You are not wrong. My Grandfather was one of the last holdouts. He wore a suit and a fedora everyday until he stopped working around 2010. He would change into a sweater and slippers when he arrived at home. It was a different time that I envy in many ways.
Muffy Aldrich in a ball cap:
https://www.saltwaternewengland.com/2023/06/remembrance-of-schools-past.html
Thanks, Old School! This looks like a good one. The post that I mentioned has pictures of men in Manhattan wearing mostly blazers and baseball hats. Glad to see you around here!
Blazer, tweed jacket, chinos – fine. Down vest over sport jacket, not so much.
Men wear baseball caps with blazers because they feel self conscious about wearing any other type of hat. So they end up wearing them with tailored items, which looks plain wrong. Ballcaps are okay with workwear, outdoorsy type stuff. I like them with badges on the front about motorcycles or old oil companies and fitted i.e. not with snap backs.. Other than ball caps, brimmed hats are now so rare that they attract stares on the street, the wider the brim the more the stares. The fedora takes you into eccentric territory in most people’s eyes. Newsboy caps were quite niche and edgy In the UK, but then every man jack was wearing them thanks to that awful Peaky Blinders TV show. In inclement weather I tend towards a pork pie, with a straw version for summer, this draws mutterings about ‘jazz’, which is okay with me.