A Beginner’s Guide to Dress Shirts for Men

A Beginner’s Guide to Dress Shirts for Men. A History of Dress Shirts for Men. A majority of men in the United States have never designed a dress shirt.  A century ago, all shirts were custom made to your specifications. You would walk into a store like J.C. Penney, look at fabrics, have measurements taken, and six weeks later, a shirt would show up manufactured for you.

Then, retailers figured out they could save a lot of money by making large runs of limited patterns in a handful of pre-designed sizes.  Customers could walk into a store, get a decent approximate fit, and have instant gratification.  This dropped costs substantially and, within a generation or two, most men had no idea that there was any other way to order shirts.

In fact, even the term “dress shirt”, which signifies a more formal pattern as contrasted to “sports shirt”, which is a more casual fabric and style, only became necessary with the rise of the t-shirt as everyday clothing.  Our great grandparents would have called a dress shirt nothing more than “a shirt”.  It was what people wore.  There really were no other kinds of shirts suitable for wearing in public.

This created an interesting split in society.  Those who had sufficient resources, or the sartorial culture, in their family continued to have their dress shirts designed, tailored, and manufactured specifically for them.  Those who lacked these inheritances believed that shirts were something you bought off a rack from a local discount retailer.  Nowhere is this split more evident than if you walk into a shirt maker’s showroom floor with someone who doesn’t know the process.  I’ve heard several friends’ remark about great clothiers, “I stopped in once but didn’t see anything I liked, so I left.”  They truly have no idea that for every one dress shirt on the showroom floor, there are 100x as many fabrics in the shirting fabric books; that the clothing on the racks are mere samples.

Bespoke vs. Made-to-Measure vs. Off-the-Rack Dress Shirts for Men

When you are looking at dress shirts for men, all shirts will fall into one of three categories: Bespoke, Made-to-Measure, or Off-the-Rack.

Bespoke Shirts are completely custom designed for you based on a pattern drawn to fit your exact body size and preferences.  Once your pattern is on file, you can order new shirts any time you want simply by flipping through fabric books.  You have total control and virtually anything you can sketch or describe can be made.

Made-to-Measure Shirts are modified based on a set of existing patterns to adjust for your own measurements and limited preferences.  If you have a fairly standard body type with ordinary proportions, there isn’t an enormous difference between made-to-measure shirts and bespoke shirts.  It may or may not be worth the additional money for you to pay for bespoke.  Your pattern adjustments can be kept on file so you can reorder when you find a new fabric you love without needing to get re-fitted.

Off-the-Rack Shirts are based on pre-established sizes and limited shirting fabrics, often by neck size / sleeve size for men.  For example, a 16.5/33-34 would be a 16.5″ neck with a 33″ to 34″ arm.

Off-the-rack shirts can be great bargains if you shop intelligently (e.g., during the day-after-Christmas sale at Nordstrom, dress shirts from Italian shirt maker Canali are priced at huge discounts, taking $275 retail shirts down to $165), you fit comfortably into a standard size, and you are lucky enough to find a pattern you like.  If you are looking for decent dress shirts for men to wear under a sweater or with a pair of blue jeans, off-the-rack shirts have their place.  The problem you are likely to face is one of experience.  Once you’ve become accustomed to having your shirts fit exactly how you want, move precisely how you desire, feel just as you like them, and be made to your specifications and personality quirks, it can be very difficult to accept anything else, even if the alternative is nice.

All else equal, even a $500 off-the-rack shirt is going to be inferior to you, as a wearer, than a $200 made-to-measure or bespoke shirt.  It always amazes me, for example, to see people buying Charvet or Brioni shirts off-the-rack at the Saks flagship store in New York when, for very little additional money, you could have them custom made to your specifications in the respective showrooms of each fashion house.

My rule of thumb: If you are willing to invest a little bit of money into your wardrobe, you should never pay more than $250 for an off-the-rack shirt, and even that is pushing it.  Beyond that price, if you are intelligent about your purchasing, you can get a much higher quality made-to-measure or bespoke shirt in the fabric of your choice, personalized down to the cuff style, collar style, and cut (“fit”) by a great shirting house.

Speaking for myself, I have no problem buying inexpensive clothes off-the-rack for casual summer ware.  In fact, I am partial to the $15 shorts sold at J.C. Penney for hot summer days when I want to sit outside and read with a glass of water and flip flops.  When it comes to dress shirts, I want spare-no-expense comfort since I like feeling good, and looking good, all day.  That makes buying off-the-rack difficult.  The last dress shirt I bought off-the-rack was a Breuer gingham at Saks for $225 nearly a year ago.

This is not a screed against off-the-rack clothing.  For some people, a nicer shirt has no marginal utility to them.  That is perfectly acceptable.  Other people should not buy nicer clothes due to their financial situation; they’d be better off repaying credit card debt or buying a home.  In short, the reason you’d buy bespoke or made-to-measure instead of off-the-rack is the same reason you’d pick a Bentley or a Lexus over a Ford.  You buy it because it is nicer and you can afford it.

The Primary Fit Styles for Dress Shirts for Men

Once you’ve chosen between bespoke, made-to-measure, and off-the-rack, you need to pick a fit.  The fit you select will depend on your body type and your personal preference.

Slim Fit shirts are tailored in the chest, waist, and arms for a closer, sleeker look.  It has nothing to do with being “slim” or “fat”.  If you like your clothes high, tight, and tailored, you probably prefer a slim fit.

Extra Slim Fit or Super Slim Fit shirts are a more extreme version of the slim fit.

Regular Fit shirts are typically close to a traditional shirting fit with slightly tapered sides.

Traditional Fit shirts are cut more like a box.