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Winter Suited & Booted

January 16th, 2013

It’s been a very mild winter here in NYC.

For the most part, my overcoats have remained closeted in exchange for heavier suiting fabrics – and nothing goes better with a heavyweight suit that a sharp pair of boots.

For the past few seasons I have been using Ariston Cloth exclusively for my bespoke suits. The third generation Neapolitan mill makes some of the most unique, tasteful and luxurious fabrics available – I highly recommend them.

Here are three of my favorites this winter.

1. A Little Punk on Park Ave


This is one of those suits that you wear more often as separates. It’s an awesome blazer with dark jeans and an even better pair of trousers with a black leather jacket.

Every once in a while, though, you want to make a statement. And the full glenplaid suit certainly accomplishes that.


Keep in mind, depending on your line of work and your office culture, a plaid this bold may not be appropriate. In a conservative corporate setting, for example, this is typically too strong for an up-and-coming analyst.

That said, the jacket can be styled more conservatively. For example, with solid light grey trousers and a simple shirt/tie combo, it could be perfect for “casual Friday”.

Just have to know your office, and your role.


These pants are much more versatile than I anticipated.

Styled properly, they work just as well for an early morning on Park Ave as they do for a late night in Bushwick.

  • Grey tortoise shades by Matsuda ·
  • Plaid flannel suit ·
  • Grey stripe contrast collar shirt by Ralph Lauren Black Label ·
  • Burgundy Pindot Tie by Polo Ralph Lauren ·
  • White cotton pocket square ·
  • Watch by Montblanc Timewalker Automatic ·
  • “Brooklyn” slim briefcase by RO Bags ·
  • Black leather wingtip boots by Paul Smith

2. Flannel Suit, Suede Chukka


I remember the first time I put on a flannel suit. It single-handedly reshaped the way I looked at fabric and tailoring.

Quality wool flannel is not only soft, warm, and durable, but also has an intriguing depth and beautiful drape.


Simplicity is mature and masculine, but it doesn’t have to be boring. The pieces in this look are subtle and refined, but not “plain”.

From my experience, the more closely a person has to look to find the real charm of an outfit, the more they appreciate it.

In many cases, good taste is knowing when not to put emphasis.


Just because you’re wearing them with a suit doesn’t mean your boots have to look brand new.

These chukkas are a little scuffed and imperfect – just the way I like them.

  • Gold Plated hand-engraved shades by Matsuda ·
  • Pink stripe shirt ·
  • Beige/Pink Silk/Wool glenplaid tie by Marshall Anthony ·
  • Polka dot pocket square Vintage ·
  • Watch by Montblanc Timewalker Automatic ·
  • Brown suede boots by Massimo Dutti
  • · Blue flannel suit

Wool Flannel Suit in Navy

3. Country Tweed, NYC


As I mentioned in a prior post, I recently made some fit adjustments to some of my bespoke patterns. This new fit, still slim but inching closer to “classic”, is not only more comfortable but can also be more flattering, in my opinion.

The jacket is a touch wider across the shoulders, roomier in the upper back, and, most noticeably, longer through the body. The pants are wider through the leg, pleated, and hemmed with a slight break.

This change is due partly to my style maturing, but also partly as a reaction to the current state of suits among style-conscious men. Especially young men. The way I see it, the ultra-slim-fit obsession is going too far – in many cases suits have become tight and have lost all the romanticism of their drape.

A slim suit flatters a man because it creates a lean shape, but a tight suit makes a man look larger and uncomfortable.

More on this later…


Recently I’ve been a big fan of the “makeshift three-piece” using a mis-matched waistcoat.

It’s a great way to mix complimentary colors and textures – like this forest green donegal tweed and camel hopsack.


Nothing finishes off a well-tailored winter look like a badass pair of oxblood dress boots. #Beast

  • Camel hopsack Vest ·
  • Burgundy/Tan check shirt ·
  • Brown flannel tie ·
  • Brown wool flannel pocket square by Armstrong & Wilson ·
  • Watch by Montblanc Timewalker Automatic ·
  • Canvas & leather tote bag by Mismo ·
  • Oxblood captoe dress boots by Scarpe di Bianco
  • · Forest green donegal tweed suit

Forest Tweed Suit


Thanks, as always, for reading.

Yours in style,

Dan Trepanier


Photography by Alex Crawford