Tailored, But Casual
I think most men want to look well-tailored, but not overly dressed-up. One solution is to wear casual, unstructured sport coats over equally casual button-up shirts. Perhaps shirts with crisscrossing plaids, such as madras, or ones made from “rougher” weaves, such as oxfords or chambrays. The bigger and bolder the pattern, or rougher the weave, the more casual the shirt is considered.
In some parts of the States, however, even that would look too dressy. Which is why I assume some men wear sport coats over t-shirts. The problem with this, besides the fact that you’ll look like you’re stepping off an MTV set, is that the chasm between the formality of the sport coat and casualness of a t-shirt is too big. There’s also no collar to frame your face or long sleeves to give the requisite show of some shirt cuff.
The best alternative, then, is the long-sleeved polo shirt. The long sleeves will ensure that no skinny wrists will ever be exposed, and the collar will give you the same effect as a dress shirt. The only difference is that nobody will mistake you for having just come from the office.
My favorite version on the market is by Kent Wang. His long sleeve polos are slim enough that they appear to be more than sportswear, and the reinforced collarband means that the collar will stand up on its own and not disappear underneath the jacket’s lapels. He has them made from different fabric weights. I prefer the heavier, denser weaves, but the others are just as wearable. For hot days, they may be even preferred since they’ll breathe more easily. Other good sources include Drake’s, Sunspel, and Brooks Brothers. Brooks doesn’t seem to have anything good this season, but last year they had a decent cream-colored model that went on sale.
You can wear this combination with casual wool trousers, perhaps those made from open-weave tropical wools, or cotton chinos. Footwear options should be equally casual. Derbies and slip-ons should be preferred over oxfords. When these are all put together you’ll achieve that perfect balance that many men look for today - tailored, but casual.
(Photos above taken from Drake’s Diary)