This is the intersection of so many things that I like, it’s almost sick.  Star Wars menswear art by John Woo (not that John Woo).

(Images via The Pursuit Aesthetic)

In the fall of ’07, bolstered by a strange fascination I had at the time with The Specials, I decided I wanted to purchase a great pair of black and white saddle shoes.  This is weird on a few levels, namely that I just tried to find a picture of anyone in The Specials wearing saddle shoes and wasn’t able to do so, even after a stalker-deep Google search.  So, I’m not sure where I got the idea that they wore them.  Also weird that I wanted to dress like a semi-defunct British ska band, but it must have resonated pretty deeply, because I also bought a pair of Fred Perry suspenders for the same reason and wore them in public approximately once.

Anyhow, after resigning that I couldn’t justify buying the pair of saddle shoes I saw in the Bergdorf’s window on my entry-level PR budget, I went ahead and got a tan and brown suede pair from J. Crew (you can see them in an earlier post here).  There were a few problems.  As anyone else who wears a size 12 or bigger can tell you, sometimes shit doesn’t translate well that large.  These shoes were huge and clunky, which led to problem #2: at the time, the only jeans I owned were skinny (thankfully that fact cannot be traced to any sort of ska style inspiration).  Still held captive by the shackles of a business-casual dress code at work, I refused to wear khakis outside of the office.  So, after a few ill-fated attempts, the saddle shoes pretty much sat in my closet for about a year, until I broke them out again last spring and found that, like everything else you wear, the likelihood of any piece of clothing or footwear succeeding for you increases dramatically if you don’t give it too much thought.  I wear them now pretty regularly.

Had my saddle shoe fixation kicked in a few years later, I would have had a lot more options.  Saddle shoes are all over the damn place this spring, and don’t appear to be letting up any time soon, with more styles rolling out by many designers this fall.  Forgiving my shoddy Photoshop collage above (I’m tired), you can see a few current and upcoming offerings from Mark McNairy, Florsheim by Duckie Brown, Billy Reid and Opening Ceremony.  I’ve already showed you some great ones from Band of Outsiders, and there are more popping up every week on the blogs.

So, I guess being a clothes-hoarder and holding onto those J. Crew suckers did have its upside.  Since I already have the saddle shoes, I can spend my money on other items brought on by bouts of 80′s nostalgia.  LIKE THIS.

Every so often, men’s magazines extoll the virtues of “all gray everything” as an alternative to black on black or a respite from bold prints and bright colors that menswear designers offer each spring.  In truth, it’s not difficult to find a huge variety of well-designed pieces in gray in any season, across a spectrum of labels and price points.  Dressed up or down, gray is versatile and easy to wear.  Details on some of my current picks and where to buy them after the jump.

Norse Projects Borderline Crew Knit in Heather Grey, £95
Available at Oi Polloi

Rag & Bone Hammer Shirt, $275
Available at Odin

Super Flat Top Sunglasses in Gray, $131
Available at Revolve Clothing

Florsheim by Duckie Brown Weld Brogue, $425
Available at Odin

Rodarte “Radarte” Hoodie, $155
Available at Opening Ceremony

Raf Simons x Fred Perry Roll-Neck Intarsia Sweater, $375
Available at Opening Ceremony

Company of We Steel Captain Sports Blazer, $294
Available at Oak

Band of Outsiders Raglan Cropped Sleeve Sweatshirt, $189
Available at Odin

Warriors of Radness Black Stone Officers Jean, $138
Available at Oak

Tretorn Grey Hockey Boot Puffer, $95
Available at Urban Outfitters

Weeks after the Band of Outsiders AW10 presentation in New York, I keep coming back to these great saddle oxfords.  Everyone was talking about the staging of the presentation (the kid swinging from the chandelier was an inspired touch) but I really think this was a standout collection outside of the theatrical flourishes, too — capped off with smart details like these shoes.

(Photos via Luxist)

Most likely a reaction the DB’s of my youth, immortalized in the First Communion photos at my parents’ house, I’ve pretty much had a blanket policy against them since I first started dressing myself.  Turns out, that might have been a bit harsh.  The Company of We version nods to its brass-buttoned forebearers, but the slim fit downplays it stodgy past.  Worn with a t-shirt, it’s smart, but definitely on this side of casual.

Company of We isn’t the only label giving the DB another chance live outside of mafiosos and 80′s business tycoons; they’ve been featured prominently in SS 2010 collections from a whole spectrum of designers — from Alexander McQueen to Michael Bastian and everyone in between.

(top row: Company of We, Bottega Veneta, Michael Bastian; middle: Alexander McQueen, Band of Outsiders, Neil Barrett, bottom: Dries van Noten)

The 80′s reference is there, but designers sent them down the runway paired with jeans, shorts, open collars, and boat shoes, updating the look to reflect a more current sensibility.  So, maybe my mom was just ahead of her time when she forced me to rock one back in the early 90′s.  In which case, let me be the first to announce the return of Starter jackets.

Or not.

(Photos via Company of We and NYMag.com)