Specifics to look for include:
- Caps should be low-profile with unstructured front panels; not the foam fan structured hats favored by large farm equipment operators.
- The bill (also called a visor) should be preshaped; not flat. The bill should always be worn at a right angle; never slanting upwards.
- There should be six fabric panels; no mesh, with matching cloth undervisor.
- The obvious fabric is 100% cotton twill. Cotton canvas qualifies as does wool; synthetics do not.
- Preferably, the cap should be a single color. Ideal colors are Navy, White, Khaki, Hunter and at times a bright Pink. The combination of Hunter Green and Khaki and Navy and Khaki are exceptions and acceptable.
- Any logo needs to be embroidered, not printed. It goes without saying that the logo be tasteful.
- They should be fastened with a cloth tuckaway back-strap or with a leather strap and a brass buckle and grommet. No plastic tabs.
- It should be fastened snugly. Nothing looks worse than a loose fitting caps.
- Women should never wear their hair down when wearing a baseball-style cap. It should always be pulled back. Ponytails should be under the bottom edge of the cap - never through the hole in the back.
- It should have tonal sewn eyelets and buttons.A clip is always a nice feature, especially for sailing.
While to many this list may seem overwhelming and even trivial, to others it will provide a framework to help understand why some people wearing some hats look the way they do.

3 comments:
These are caps, not hats.
Technically, a cap is a type of hat, but I like your more specific descriptor, and will make the change. Thanks!
I must take issue with one point, for the women...
I simply do not look good in low ponytails, whether there is a baseball cap on my head or not. As such, although all my caps meet all of your criteria for attractive caps, I do pull my ponytail through the hole in the back. To leave the ponytail below the cap is to have the ponytail hang very low. There is just something about my appearance which cannot accommodate that look. Fear not, my hair doesn't end up looking like a 1950s cheerleader, and I don't pull the hair through and secure it with a giant scrunchy, or anything like that. I use a subtle, thin, Goody hair elastic. I've examined the look from all angles, and it looks much better than having the ponytail hang low.
I think on this one, people really have to go with what works for them and not with any hard-and-fast rule.
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