Causal Dress Shirts

If you want to dress down a tailored jacket, there are few better ways to do it than wearing a casual dress shirt. Things in slightly more textured or patterned materials will be less formal looking than your traditional, solid white and light blue broadcloths, and make you look less like you’ve just come from the office. In his books Dressing the Man and Clothes & the Man, Alan Flusser has some suggestions that I think are particularly good. A few of them are pictured above. All are unique enough to be casual, but also still unassailably in good taste. 

Some other pointers for picking good, casual dress shirts:

  • Stripes work year-round, but checks can sometimes be seasonal. Gingham and madras, for example, work better in the warmer months, while tattersalls, graph checks, and tartans look better with the tweeds and corduroys we wear in the cooler seasons.
  • Although light blue is a staple for many men, don’t be afraid of colors such as burgundy and dark green. Just get them in patterns, instead of solid colors.
  • Forgo the tie, especially if your shirt is particularly casual (e.g. busy patterns or non-traditional fabrics). 
  • Remember: the bolder the pattern, the more casual the shirt.
  • Consider less-formal materials. Brushed cotton flannels, chambray, and wool-cotton blends have a visual heft that goes well with tweed jackets. Linen and madras, on the other hand, are good with summer jacketings. 
  • Small collars can give you a very modern look, but they’re more likely to collapse underneath your sport coat when you’re not wearing a tie. If you want your collar to stand up, you have two options. The first is to go with a button down collar, which will stand up once you fasten the collar points. The second is to get a semi-spread collar with a tall enough collar band, long enough points, and stiff enough interlining. Be careful to not get something too big or stiff, however. Things can quickly look cheesy. I think our advertiser Ledbury has a particularly nice collar for wearing casually with sport coats. 
  • Shirts with a slightly lowered second button will give you a more attractive neck line when your collar is unbuttoned. Again, our advertiser Ledbury does this well. You can also request it on custom shirts. I use Ascot Chang and think they do a great job. For other options, consider MyTailor, Dege & Skinner, and CEGO (the last of which you have to be in NYC). For online made-to-measure companies, check out Cottonworks and our advertiser Proper Cloth. We have a series on custom shirts that can help you through the process.

You’ll rarely go wrong with a solid white or light blue shirt, but if you’re trying to dress down a sport coat, consider more casual options. Again, any of the patterns in Alan Flusser’s guides above would be a great place to start, so long as you pay attention to the details. 

Modern Tailor: First (and Second) Impressions
A month or two ago, the Chinese made-to-measure operation Modern Tailor offered a special introductory offer: a basic oxford shirt for $19.95. I jumped at the opportunity to try out the overseas, internet-based MTM experience. I’ve finally got my shirts in hand, and thought I’d offer a quick review of the process and product.
The Status Quo
Most of my shirts come from one of two sources: the New York made-to-measure operation CEGO or the thrift store. At CEGO, Carl Goldberg (who runs the joint) measured me in person, and offered me an array of fabrics, including both bolts and swatches. He’s a genuine expert, whose advice is immensely valuable. When I order from him, I know what I’m getting, but the prices are (by my modest standards) steep. Shirts usually end up costing around $150 - an amount I could best afford when I had a small wardrobe budget for my TV show.
Thrift store shirts are much cheaper, of course, but they have their own problems. Fit is iffy, even with alterations, and you have to take what you find, style-wise. It can be difficult to build a basic wardrobe through thrifting.
My hope was that online made-to-measure might fill the gap, especially for the readers who write me with difficulty finding any off-the-rack shirts that fit. The answer? Yes. It might.
The Process
I found the ordering process at Modern Tailor simple and clear. I grabbed a shirt that fit me well (one of my CEGO oxfords) and took measurements from that with a seamstress’ tape. Input was easy, and my order was processed very promptly. Too promptly, as it turned out - I realized a few hours after clicking “send” that I had forgotten to account for shrinkage.
Customer service at MT was extremely helpful. They tried to correct my order, but it had already gone into production, and they instead offered to send me the shirt in production for free, and allow me to adjust measurements for the three shirts I ordered on that basis. Shipping was prompt (took about two weeks, total).
The shirt, when it arrived, had all kinds of problems. The fabric wasn’t what I’d expected. An oxford, yes, but a very, very lightweight one, almost untextured. This is, of course, the kind of problem one can reasonably expect from online - if you don’t have the fabric in hand, you can’t judge it well. (Modern Tailor does offer a swatch book, which comes with some coupons, for $25.)
The sizing was badly off. I’m not sure if it was my measurements, laundry shrinkage or a manufacturing mistake - my guess is a mix of the former two - but it was simply unwearable. Customer service at Modern Tailor was happy to wait for adjusted measurements, though, and I finally found time to make the appropriate changes.
The final shirts were made promptly thereafter, but were apparently held at the post office for a few weeks. My mailman never left initial notice (they require signature on delivery), and only left a second notice after Modern Tailor inquired as to why the package hadn’t been delivered.
The Product
You can see the results above. The pattern still needs some tweaking - it’s tight in the shoulders and the waist. (Unflatteringly so in the waist… that I posted it on the internet is a sign of my commitment to you, the reader.) There are also things an in-person shirtmaker can account for, like shoulder pitch and posture, that are tough to impossible for online to handle, even when measuring from a perfectly-fitting shirt.
The cuffs have a stiff interlining that I’m not crazy about. The mother-of-pearl buttons (an extra couple bucks a shirt) are quite nice. The shirts, as they are, are very wearable and were a bargain at $20. Would I buy them regularly at the standard $60 price point? What about $100 or $150 for premium fabrics? I’d have to consider it.
The Bottom Line
There are people for whom it’s very difficult to buy clothes that fit off the rack. The very tall, the very thin, the very thick, the lopsided. Some of those folks can afford to consult with an expert shirtmaker - and I recommend that those do. For those who can’t afford it, online custom is a reasonable substitute.
The process is fraught with challenges. You’re not a professional measurer. You may not have a shirt to measure from. Shirts may vary in manufacture. It’s tough to judge fabrics without experienced advice and in-person evaluation. These are smaller problems in shirts than they are in suits (witness the disastrous online MTM tailored clothes that show up every day on the clothing fora), but they’re significant problems nonetheless. The end result of all this is that it’s more of an adventure than a luxury. I’d certainly send a friend to CEGO before I’d send them to Modern Tailor.
That said: I think there is a place for this kind of operation for those with developed taste and specific needs, but slim bankrolls.

Modern Tailor: First (and Second) Impressions

A month or two ago, the Chinese made-to-measure operation Modern Tailor offered a special introductory offer: a basic oxford shirt for $19.95. I jumped at the opportunity to try out the overseas, internet-based MTM experience. I’ve finally got my shirts in hand, and thought I’d offer a quick review of the process and product.

The Status Quo

Most of my shirts come from one of two sources: the New York made-to-measure operation CEGO or the thrift store. At CEGO, Carl Goldberg (who runs the joint) measured me in person, and offered me an array of fabrics, including both bolts and swatches. He’s a genuine expert, whose advice is immensely valuable. When I order from him, I know what I’m getting, but the prices are (by my modest standards) steep. Shirts usually end up costing around $150 - an amount I could best afford when I had a small wardrobe budget for my TV show.

Thrift store shirts are much cheaper, of course, but they have their own problems. Fit is iffy, even with alterations, and you have to take what you find, style-wise. It can be difficult to build a basic wardrobe through thrifting.

My hope was that online made-to-measure might fill the gap, especially for the readers who write me with difficulty finding any off-the-rack shirts that fit. The answer? Yes. It might.

The Process

I found the ordering process at Modern Tailor simple and clear. I grabbed a shirt that fit me well (one of my CEGO oxfords) and took measurements from that with a seamstress’ tape. Input was easy, and my order was processed very promptly. Too promptly, as it turned out - I realized a few hours after clicking “send” that I had forgotten to account for shrinkage.

Customer service at MT was extremely helpful. They tried to correct my order, but it had already gone into production, and they instead offered to send me the shirt in production for free, and allow me to adjust measurements for the three shirts I ordered on that basis. Shipping was prompt (took about two weeks, total).

The shirt, when it arrived, had all kinds of problems. The fabric wasn’t what I’d expected. An oxford, yes, but a very, very lightweight one, almost untextured. This is, of course, the kind of problem one can reasonably expect from online - if you don’t have the fabric in hand, you can’t judge it well. (Modern Tailor does offer a swatch book, which comes with some coupons, for $25.)

The sizing was badly off. I’m not sure if it was my measurements, laundry shrinkage or a manufacturing mistake - my guess is a mix of the former two - but it was simply unwearable. Customer service at Modern Tailor was happy to wait for adjusted measurements, though, and I finally found time to make the appropriate changes.

The final shirts were made promptly thereafter, but were apparently held at the post office for a few weeks. My mailman never left initial notice (they require signature on delivery), and only left a second notice after Modern Tailor inquired as to why the package hadn’t been delivered.

The Product

You can see the results above. The pattern still needs some tweaking - it’s tight in the shoulders and the waist. (Unflatteringly so in the waist… that I posted it on the internet is a sign of my commitment to you, the reader.) There are also things an in-person shirtmaker can account for, like shoulder pitch and posture, that are tough to impossible for online to handle, even when measuring from a perfectly-fitting shirt.

The cuffs have a stiff interlining that I’m not crazy about. The mother-of-pearl buttons (an extra couple bucks a shirt) are quite nice. The shirts, as they are, are very wearable and were a bargain at $20. Would I buy them regularly at the standard $60 price point? What about $100 or $150 for premium fabrics? I’d have to consider it.

The Bottom Line

There are people for whom it’s very difficult to buy clothes that fit off the rack. The very tall, the very thin, the very thick, the lopsided. Some of those folks can afford to consult with an expert shirtmaker - and I recommend that those do. For those who can’t afford it, online custom is a reasonable substitute.

The process is fraught with challenges. You’re not a professional measurer. You may not have a shirt to measure from. Shirts may vary in manufacture. It’s tough to judge fabrics without experienced advice and in-person evaluation. These are smaller problems in shirts than they are in suits (witness the disastrous online MTM tailored clothes that show up every day on the clothing fora), but they’re significant problems nonetheless. The end result of all this is that it’s more of an adventure than a luxury. I’d certainly send a friend to CEGO before I’d send them to Modern Tailor.

That said: I think there is a place for this kind of operation for those with developed taste and specific needs, but slim bankrolls.

Episode 3: Clothing Credits

Intro:

Suit - J. Crew

Shirt - Thom Browne

Tie - Carrol & Co. (Vintage)

Square - Vintage (Courtesy: Grand-Uncle Philbert)

Shoes - Nordstrom

On Set

Suit - J. Crew

Shirt - CEGO Custom Shirtmakers

Tie - Courtesy  of Berg & Berg

Shoes - Gieves & Hawkes

Square - Holland & Holland

Nerd Boyfriend Picks

Jacket - J. Crew

Shirt - Uniqlo

Pants - Hentsch Man

Shoes - American Apparel

On Roxana

Shirt - Marc Jacobs

Skirt - Marc Jacobs

Rudiments

Tie - Turnbull & Asser

Q and A

Blazer - hickey

Shirt - Lands’ End

Pants - Incotex

Tie - Benjamin Bixby

Shoes - Sebago (Vintage)

Square - Grand-Uncle Philbert