Archive for November, 2023

The world keeps getting more casual while us trad’s try to remain the same. I’ve always struggled with casual outfits. When I say casual I don’t mean business casual. I am talking about Saturday type casual. I’ve had some success with switching out my chinos for green fatigue styled pants, wearing flannel shirts, and by leaving my shirts untucked. Lately I decided to branch out even further.

The trad’s instinct is to always wear an OCBD under a sweater. This is a great instinct because the shirt keeps wool off your skin and the OCBD collar gently protruding from under the sweater just looks fantastic. The problem is that this is my go to office look so it doesn’t look all that casual when I do it. Even if I swap my penny loafers for blucher mocs it doesn’t quite get there. Sneakers help, but this has been my casual Friday look. My current solution has been wearing a long sleeve t-shirt under my sweaters.

As I was writing this post I realized that this is a look that I have done done in the past. However back then I typically used a turtleneck. This is a nice way to dress this look up a touch and it still looks more casual than wearing an OCBD underneath. I am currently a big fan of the long sleeve-t though. It’s even more casual looking especially when paired with jeans, fatigues, or even our beloved chinos.

I can’t leave without mentioning how this look really helps with one specific type of sweater. The tennis sweaters or cricket sweater (depending on which side of the pond you live on) can have some 80’s movie spoiled/evil rich kid baggage. The t-shirt underneath seems to help kill a lot of that vibe. I hope this helps any of you that are struggling with those weekend casual looks. Before you ask, I just wear Hanes or Fruit of Loom long sleeve t’s!

This week I am back with another installment of people watching. Although he longer posts this UK based all-around cool guy who goes by Charlie don’t surf on IG (see here) continues to give me inspiration. Specifically he gives me fall/winter inspo with his casual-leaning-heavy-duty-rugged-ivy style mixing trad, ivy, and old school/new school gorp with fantastic results. It reminds me of an updated version of the 70s trad looks that HTJ used to post and it is really good.

Here’s how he does it. He goes for a boxier straight but not super baggy silhouette. The pants are almost always denim, but there is the occasional corduroy 5-pockets in brown. The shirts are OCBDs in blue or white. His shetlands are typically earth tones. The outerwear is rugged 70s gorp (down jackets, down vests, 60/40 jackets, etc.) and always offer a nice contrast with his sweater. The shoes are casual, often chunky and suede (Padmore 204s, camp mocs, Paraboots, desert boots, grey New Balance). His accessories are a cap (bucket or baseball) and a ribbon belt in green/red. David’s style is a study in silhouette, color, and texture. Couple that with his knowledge of self and you have some very very good fits.

A few takeaways. David’s reinforces my belief that a simple uniform style approach to getting dressed is the way to go. He keeps it simple, does variations on what works for him/what he likes, and it pays off. I have never really been into low top wallabee style shoes or ribbon belts, but now I am considering both. If you like his old school outdoor outerwear look for older REI, L.L. Bean, and brown label North Face on Ebay. You know I love my old green down vest. David is more proof that you can look cool wearing trad/ivy and that it doesn’t have to be all heyday, repp ties, and navy blazers even though that’s cool too.

After checking out this post you might also enjoy, The Late 70s Prep Checklist that I did back in 2015. It can provide some more inspiration for this style. I’ve included more pics of David below. Be warned, when imitating these looks that he is a very cool guy and your results may vary. Have a great weekend!