A Montecristi blocked into a derby shape.  For the dedicated collector.  Photographed at Optimo, Chicago. — A Montecristi blocked into a derby shape. For the dedicated collector. Photographed at Optimo, Chicago.

A head, unlike a waist, doesn’t fluctuate seasonally, and unless a person loses or gains a significant volume of hair, once a good measurement is on file with a hat-maker, the task of ordering really becomes a styling exercise. With creases, dents, crowns, welts, brims, bindings, bands, and bows to consider, this is no trivial task, but compared to the multiple appointments necessary for a suit, a visit with a hatter is comparatively brief. When your hatter is Optimo of Chicago, brevity is a shame; between all the dense felt, the spools of grosgrain and billowing steam, it is a particularly evocative place. I have often been in the shop and witnessed other customers finding reasons to linger well-past orders have been placed. Others might have noticed the same of me.

The hat wearer is considering straw at the moment. At the top of that broad, warm-weather category is the Montecristi, the finely woven toquilla straw hats from the namesake Ecuadorian city. Ultrafino qualities can run into the thousands and are highly collectible; the best I’ve handled was basically indistinguishable from linen. Regular Montecristis are also beautiful, and less likely to cause a man-overboard scenario if blown from your head while boating. Whether the finest or the entry level, Montecristis project a crisp, formal character; they can be worn casually, but seem to reward those unafraid to dress for an occasion.

Further down the price spectrum is my personal favorite—the Milan (MY-lan). This courser, golden weave has a variegated texture and a rich seagrass aroma. Mine started life quite stiff but has softened and fuzzed over time, exchanging some of its blocked shape for a slouchy, well-worn character. It is head, rather than hat-shaped and accompanies nothing more formal than a shirt worn open at the neck and loafers.

Milan seams to do best in a standard teardrop crown with a soft pinch and brown-toned hat band. More exciting bands with tonal or contrasting stripes can be very handsome, but limit somewhat the hat’s compatibility with other clothes. Montecristis classically have a black band; the contrast is perfect next to the pale cream straw, like a calligrapher’s bold underscore on a luxurious calling card.

But don’t linger over these choices for too long; Memorial Day, the traditional start of straw season, approaches.