A Gent @khakinehal has asked what kind of outfit goes with baseman shoes (wingtipped boots). I just love a good pair of boots and wingtips are perfect for casual outfits. They will go with pretty much any outfit including dark wash jeans or chinos.
For a couple of ideas, if you've got some dark brown ones (don't get tan or light brown), pair it with some navy chinos and a white linen short sleeve shirt - perfect for Spring.
If you've got a black pair, have you thought of an all black outfit? Even in spring these work. Get some black jeans, black t-shirt and a black dress watch - perfect any time of the year.
With boots it's important to get your trouser length right. You don't want the fabric gathering at the bottom. So you either need a pair of your shorter trousers or you need to roll them. If you do roll, just a couple of tight rolls will do, making sure they are flat against your boot.
Hope this helps 👍👍👍