I’m leaving for NYC tomorrow. I’m counting it as a vacation, but I’ll definitely be doing a lot blog work while there - meeting with vendors, trying on awesome clothes, taking pictures, writing - sounds terrible, doesn’t it?

Oh, and since I always get so many questions about where each item comes from in these posts, I’ve included product links when available. Keep in mind, though, that none of these items were bought at full price and many were bought used.

Here’s what’s going with me:

Hopefully I’ll get to meet some of you all while I’m there! You can find my other packing posts here.

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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. 

WIWY: Classic

In the past year, the menswear community has really begun to feel the tides change from “slim is in” to “relaxed fit is right,” i.e. the classic “shape vs. drape” argument. I’m sure this will ultimately pass through the median “classic” point and head to the other side of the spectrum, as it always does. It is as if the menswear community is constantly trying to recover from the previous extreme, and in doing so enjoys a brief moment of classic proportions before heading into the opposite camp (or perhaps that is just my own personal experience). This pendulum behavior seems perfectly natural, and is quite nice in brief moments like these where both skinny and wide ties are passé, trouser legs are moderate in size, and the pleat/no pleat argument is a matter of taste, not some sort of ultimatum. However, it is in these instances that I feel most strongly that “classic” style can’t be unanimously described in inches of tie, lapel and trouser fabric. In my mind classic style is one part historical and one part what looks right on you.  I’ve put together this look as my nod toward classic proportions, while acknowledging my own body type and personal preferences.

Some hard numbers: 3” jacket lapels, 3.25” tie, 8” trouser leg opening (slight break, classic rise, mild taper), classic-leaning (butt-covering) 29” jacket length. Nothing skinny here - except for me, of course.

Shirt - Proper Cloth | Tie - Vintage Polo RL (ebay) | Blazer - Part of a suit - Thick as Thieves | Flannel trousers - Howard Yount | Shoes: Sid Mashburn (ebay) | Pocket Square - The Tie Bar

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Over the past couple of days my girlfriend Mary and I have taken nearly a thousand photos at men’s clothing events and have had many great conversations with some of the best in the menswear business. It’ll be a day or two before I can start posting more extensively about what I’ve seen and learned while in NYC (I am on vacation, after all), but stay tuned for lots of great content over the next week or two! 

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