Congratulations to Steve, the winner of this Outfit of the Week!

A $250 gift card to Imperial Black is coming to you, Steve.

We asked you guys to give us your best look that expressed the idea that “eloquence always get you out of trouble”. Here’s what Steve had to say about his look:

I actually thought for a while about the ‘get out of jail free’ outfit. Would someone in authority be more likely to reward conformity – i.e. the menswear uniform, pulled of with impeccable style and detailing; or a maverick who might be a bit of a wild card? My first thought was the former. A cop, a security guard, etc. might want to see someone who is playing by the rules in fashion and cut them a break for bending a rule or two in the real world. But my experience has been somewhat the opposite. When I’ve gotten myself into (and subsequently out of) hot water it’s been because I carry myself with enough moxie to make people believe I know what I’m doing or that I have the authority to adjust the rules.

For that reason, I went for a look I consider sharp but definitely takes creative liberties. I’m in FL so a lightweight jacket is a must. Double monks are dressy, but no socks – not radical anymore but still uncommon outside of a small group of menswear folk – keeps it informal. Since I opted for color in the pants, a plain white shirt seemed like my best option. Stuff a pocket square in for good measure and you’re ready to convince the bouncer you belong in the VIP section or explain to your boss why your two hour lunch break was a good thing.

Gabi’s Take
They say the devil’s in the details, and I think the details in Steve’s look are exactly what would get him out of trouble. The stripe in his tie is perfect with his pants, and that wee little blue square of fabric on his double monks? Yeah we noticed that, and how it perfectly coordinates with the pocket square, even though you won’t see both from the same angle. Those things get you noticed.

Megan’s Take
You guys know I love a colored chino, so of course I was immediately taken with Steve’s look. Add that to the sock-free ankle, and that great pocket square just peeking out, and I was sold. As for what he can get away with, I don’t see anyone coming to get him down from that fence, so I’d say his “get out of jail free” style is working just fine.

And we couldn’t forget the outfit details:

Jacket: J. Crew Factory
Shirt: Geoffrey Beene Pants: Arizona originals
Shoes: Bar III for Macy’s
Tie: Vintage thrift (“sear’s men’s store”)
Belt: Vintage thrift (Perry Ellis portfolio)
Pocket Square: personal DIY project

Tell us,

What’s your ‘get out of jail free card’ outfit?