Friday the 13th?! Uh oh, I hope I’m not bestowing bad luck on this week’s winner.

And that’s…

Jose!

Jose snaps up the Johnston & Murphy Clayton Double Buckle dub monks for his well-layered look.

Guys, I cannot tell you how tough it was to select this week’s best-dressed reader. Every one of you  brought your A-game to this fall look challenge. I’m not even kidding you, nearly any of you could have taken the top spot. And it wasn’t just the pictures; your explanations of why you’re wearing what you’re wearing have gotten so sophisticated! Either you’re actually retaining the info you read on here, or you’re just getting more verbose. Either way, I like it. Because everyone who entered was a total stylish, well-spoken (err, well-typed)  stud.

That said, Jose really knocked my socks off. And his description really got me, for a few reasons I think you’ll recognize.

Well, I’ll let Jose tell it:

“I’m teaching a class at my job all this week and felt kind of scholastic and with fall approaching though it was a great time to breakout my rugby shirt. It’s fairly thin and not too heavy so layering it wouldn’t be too hot. The crazy thing is that I live in South Florida and the weather is typically muggy and scorching this time of year, but between some rain clouds and the fact I spent all day in an air-conditioned room, I was able to pull it off without breaking a sweat.

These jeans I got on clearance one day at a ridiculous rock bottom price at Target. I think I paid like $5 for them. They sat unworn in my closet for quite some time until I decided to take them to a tailor. I had them tapered and shortened. Now I wear them all the time because they are a perfect fit and the wash is so versatile (SG note: Yeahh!!!!!).

I got the rugby shirt after seeing a post on another blog. I had been looking for a rugby like this one but all the ones I found were so expensive. I have two kids so I need to find cheaper alternatives whenever I can. I got it for like $40. Not dirt cheap like the jeans, but still cheaper than the RL one I had been eyeing. I typically love layering them over the shirt and tie combo. Just really feeling that look.

The tie I got out of a clearance rack at J. Crew. Loved the forrest green and loved the little scorpions. Kind of a subtle way to have a little attitude cause no one !#$%@#$ with scorpions.

I had been on the fence about the Weejuns for some time thinking they were an old man shoe but cashed in some of my AMEX points to get them for free from Zappos figuring I could return for free if I didn’t like them. Don’t regret the decision at all now. And with the Florida heat, you know ya gotta lose the socks.

JCP made such a huge u-turn when Nick Wooster was the creative director behind the menswear line. I hadn’t stepped into a JCP in years until I heard he had changed all the styles and fit. Walked away with many of their stuff including this OCBD. I got this one as an XMAS gift, but I bought a few other ones because I loved it so much. Shame they let that man walk out the door because my business left with him.

You can’t see the watch but it’s a skeleton watch. I just really love seeing the inner workings of these things.

As far as my personal  style is concerned, I’d like to think it leans modern prep. Working tailored blazers, sweaters (when not too hot), and shirt and tie combos into casual wear. Jeans are without question my go to pant over anything else so they get worked in often.

Here’s the breakdown of Jose’s dub monk-winning look:

Rubgy Shirt: American Apparel

OCBD: JCP

Tie: J.Crew (Forrest Green with small white scorpions on it)

Bracelet: Trashness

Watch: Stauer

Jeans: Converse for Target

Shoes: Bass Weejuns

Tell us:

What do you think of Jose’s look? Would you layer your rugby shirt like he did?

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