This week’s #OOTW winner is….

Bobby!

SG reader Bobby will be rewarded for this great look with $200 to spend at styling service Trunk Club.

Here’s what the newly-minted Philadelphia lawyer had to say:

“The photo was taken after I bought the jacket in Florence – it was a gift that I gave to myself as a reward for taking the bar exam at the end of July. I really just wanted to fit in – to look like an average Italian and not resemble a tourist.  Kind of a clean, crisp look that seems natural and effortless – sprezzatura.”

Here’s Bobby’s breakdown of his outfit:

Here’s what I like:

Two things, actually.

1) Bobby made a point to intentionally not dress like a tourist on his trip to Italy. Since Americans are usually the worst offenders of the, “Me come to your country, talk loud English and wear fanny packs,” travel attitude, it’s refreshing to see the thought Bobby put into his outfit planning. At least make an effort; you can still look like yourself while giving a nod to the traditions and culture of the country you’re visiting. And I bet he’d tell you he felt supremely comfortable in his sightseeing look, despite the lack of sneakers and cargo shorts.

2) He took my advice to shop on vacation! That leather jacket is a great investment, and he’ll always have warm memories of his trip – and passing the bar! – when he slips it on.

Would I make him take those socks off if I could? Sure, but we can’t all get everything we want in life, now can we?

Gabi’s Take:

I thought you were an Italian local from the picture! Supple leather jacket, casual – slightly unbuttoned – button-up, slim khakis, and classy gent shoes: all things point to classic European styling. And it looks awesome! You managed to make a bunch of neutral colors  and basic pieces dynamic. If only more people in Philadelphia dressed like that…

Bobby, we can’t wait to see what ‘stylish young lawyer guy’ clothes you select with your Trunk Club stylist!

Tell us:

What’s the best gift you ever bought for yourself?