Thanks for the kind words about the job search!
That’s a really tough call, to be honest. The square I have is from Howard Yount and I wear it with everything. It is, however, larger than your typical pocket square, measuring 16”x16”. This causes it to be a bit thicker in the pocket and more substantial.
Unfortunately, Howard Yount no longer has these in stock (you’d have to email Jamison to see if they’ll return). You can currently find his 13”x13” one for $25 and it’s made in Italy. The one critique I have of the square is that the edge rolling seems slightly flat. It’s still textured and bumpy from the stitches, but the edge could have more thickness to it.
Vanda Fine Clothing does an absolutely superb job on their pocket square. The edges are more cylindrical in the hand-rolling and I feel they have the best craftsmanship I’ve seen on a pocket square. I have an ivory silk one from them that’s from an old kimono silk and I’m really impressed. Their linen one is also 13”x13” and I’m sure the stitching quality is of the same level. But they’re also the most expensive at about $37. Still, I believe Diana and Gerald do phenomenal work and I’m happy to support them and find their premium luxury prices are worth it.
Kent Wang's squares are slightly smaller at 12”x12”. Might seem like a trivial detail, but when I TV fold my squares over I find folding it into fourths along an edge makes it just a bit too short to fill the pocket, so I fold it into sections of 3.5”, 2.5”, 2.5”, 3.5” instead. Still, they're the cheapest of the bunch ($20) and do have a great thick edge on them.
I’ve never bought from Sam Hober — either neckties or squares — but maybe that’ll change in the future. His squares for $30 seems about on par with everything else made from an independent shop. I am fan though that his squares are 15”x15”, which might be pretty ideal.
I’m not sure there’s really a definitive answer for you. Price plays a factor. Obsession over details plays another. And it’s all over some piece of cloth that sits idle in your pocket all day. You can’t really pick a wrong one, to be honest, because most people won’t care or notice.
If it were up to me right now, I’d probably go with Vanda. I’d probably pay a little extra and have it monogrammed in the corner with my initials to add a personal touch to it. I’ve become especially fond of Vanda’s work and they’re my first preference now for ties and squares.