I love this Apparel Arts illustration. I found it last year on an online men’s clothing forum, and put it in my head to try to find similar pieces. Unfortunately, by the time I did, summer had already passed. This year, however, I’ll be wearing this on more than a few occasions once the weather gets hot (though, I’ll probably leave the ascot and pipe to more dashing men).
The great thing about this is how stylish it looks with just a few simple pieces. To get something like this for yourself, consider this long-sleeved polo from Kent Wang. Though not technically the same as what you see above, I think long sleeves rolled up look better than short ones. I also find that long sleeved polos have the advantage of being able to do double duty underneath sport coats. They show the bit of requisite shirt cuff underneath the jacket sleeve, and ensure that no bare wrists will be exposed when you move your arms. If you want something sportier, however, Kent has a number of short sleeve options as well.
The upside to Kent’s polos is that they have a few “button up shirt details” that make them look a bit smarter than your average tennis shirt. The collar band, for example, is reinforced, so the collar doesn’t flop down and lay flat against your shoulder (like you’d see on most polos). The downside, however, is that they fit very slim and the sleeves can be a bit tight. Kent has measurements posted though, and he accepts returns.
For other options, Jesse has recommended Lands’ End. I also really like this new polo at The Armoury, which I believe was made for them by Ascot Chang. To order one, you’ll have to call or email their store (expect the price to be higher than either Kent’s or Lands’ End).
Tan trousers are harder to find. For mine, I bought a pair of flannel ones from Howard Yount, but they’re sold out now and won’t be restocking until fall. Flannel has a bit of richness and mottling that’ll help keep this from looking like a Best Buy employee uniform. You can find something similar at the moment at O’Connell’s and J Press, the second of which is having a sale right now. And though they’re not tan, these Pantas look fantastic. Their prices aren’t cheap, but their pants are some of the highest quality you’ll find in the ready-to-wear market.
Finally, for the creped-soled shoes, consider some of the options I mentioned a few weeks ago. I think pair of sueded, dark brown chukkas with rubber crepe soles here would look great.