I find most dress shirts either too traditional (way baggy, with dated patterns) or too stylin’ (overly fitted, with patterns that are soon to be dated), so I’ve been thinking about going custom. There are a million options out there. What’s the best way to go about it without wasting a bunch of money in the process?

Rob B., Nashville

Yours, sir, is an all-too-common dilemma, and one that most custom shirt makers seem uninterested in addressing. The typical session goes something like this: They trot out a mind-numbing array of fabrics, collar types and cuff options; feeling a little woozy, you make a few unsteady choices. Then, four to six weeks later you’re presented with five new “custom” shirts that fit exactly like the blousy, droop-shouldered off-the-rack numbers you’ve been trying to avoid. Oh, and it’ll cost you a buck-fifty a shirt. Now, assuming you aren’t an unusual size—and that seems a fair assumption, as you probably would’ve noted that—I’d actually recommend you do a better job with brand selection.

My first piece of advice, and I don’t just say this because the name’s on my paychecks, is to regularly scan Gilt MAN for shirts from brands that design with guys such as yourself in mind. These include Seize sur Vingt and Thomas Pink on the traditional end, or Billy Reid, Trovata, or Steven Alan on the more “stylin’” side of the equation. All are dedicated to helping you look sharp while evoking neither a 50-year-old tax lawyer nor that “Hey, check out my striped shirt” guy from a few years back.

That said, if you insist on going the custom route, make sure you ask around first. See who you know that has had shirts made and been happy with the results, and take a look at how those shirts actually fit the gent in question. On top of fit, be sure to size up the details like the quality of stitching, the way the patterns match up, and the buttons.

Or, if you know your measurements, you could also do a trial order from the likes of Alexander West or Michael Andrews in New York, who produce good quality, affordable custom shirts that are measured in the U.S. but made (at significant savings) overseas. And James Jurney, the banker-turned-clothier behind the aforementioned Seize sur Vingt will be happy to make you a French-styled, Italian-made shirt if what you find on Gilt isn’t to your liking. But whatever you do, I’d recommend starting with our authoritative and gratuitously well-written piece on How to Buy a Dress Shirt.