Sutherland Wool Cashmere Topcoat | $310 (sale) at J Crew

A: It’s hard to go wrong with a suit for any interview, but of course it may be unnecessary given the industry.  Then again, there’s that saying that those who overdress may feel like idiots, but those that underdress are idiots.  Moral of the story?  Wear a (casual) suit.

I really do think that while suits are traditionally a formal look, they can also be made to look very casual.  It’s the little things that matter.  Here’s three ways you can make a suit more casual: no belt, a skinnier tie that’s loosened just a little bit, and no socks.  Oh yeah, cufflinks don’t scream "formal," they scream pretentious—especially for a creative job. Leave them at home.  Skip the contrast collar too; you can wear it when one day you’re on the other side of the interview table.

And suits can still be "edgy" – a suit by Thom Browne takes some real confidence to wear, for example.  I’d be safe (and thifty), though, and avoid the Thom Browne suit, unless you’re going into a really artsy industry (no negative connotation intended).

Sidebar: If you’re trying to get a job on Wall Street, stick to navy or charcoal and a white shirt.  You can’t go wrong with a solid or striped tie, either.  The conservative culture of such firms may cause the interviewer to frown upon anything more.  Besides, you should be more worried about trying to answer questions about WACC and Deferred Tax Liabilities than what you’re wearing.

1.  Start with a buffalo checked button down shirt. 
2.  Add a pair of dark rinse jeans (or dark trousers).
3.  Layer on a hooded parka.  Extra style points for interesting pocket detailing.
4.  Slip on a pair of loafers.  Loafers are nicer than sneakers, yet they’re still casual enough for this outfit.

In recent years, one-strap bags (“messenger” bags) have become the craze, if not the cliché.  I can see why: they’re practical, more refined than most backpacks and not unstylish.

Who should wear it: College students, IT guys.
Who shouldn’t wear it: White-collar types (unless you’re traveling).

The briefcase is the most refined “bag” a man can have – and accordingly, it’s usually the most expensive.  A briefcase is a statement that you’ve made something out of your life (career wise at least).  Formal and usually made out of luxe materials such as high-grade leather and precious metals (think 24k gold metal locks), briefcases mean business.  But keep in mind there are two types: soft and hard.  Both are pretty much office standards, but the soft ones are a bit more informal.  Keep your briefcase simple and traditional: get one in black or dark brown.  Skip the high tech ones like the $16,000 carbon fiber piece from Hermes.

Who should wear it: White-collar types.
Who shouldn’t wear it: Anyone that’s not a white-collar type – you’ll come off as pretentious.

I don’t know if there is technically a difference between a duffel and weekend bag, but I tend to think of a weekend bag as a more refined version of the traditional rugged duffel.  Weekend bags are really for those guys in New York who want that 3 day trip to the Hamptons or Maine and need something to put clothes, shoes, bottles of wine, and whatever else you want to put in there.  And that’s the beauty of it; it really is a holdall bag – just throw you’re stuff in there. One of my favorite pictures on The Sartorialist is of Michael Bastian wearing a wrinkled dress shirt, Nantucket reds and loafers, while trying to hail a cab carrying a weekend bag (ok it’s a duffel bag…I guess Mr. Bastian can make even duffels look cool).

The downside of weekend bags is that they are a luxury: you don’t really need them.  As a result, most good ones are expensive.  If you do get a weekend bag, though, pay a little more and get one that’s well made.  I like the motto, “Beat up the pretty things;” it describes exactly how I’d treat a beautiful weekend bag.

I don’t know what’s happening, but the level of sloppiness in what some guys are wearing is simply getting out of hand.  Loud colors, ill-fitting clothes, sunglasses at night– it’s not stylish, it’s sloppy.

If you want to look as if you don’t care, that’s fine, but please do it with style.

Or more specifically, with sprezzatura, the Italian term for “artful dishevelment” as I call it (it’s not a literal translation).  You may do it already without knowing: sprezzatura is dressing like you don’t care, taking a nonchalant attitude with your appearance—when in fact you do take time and effort to create your look. 

The trick to pulling it off is subtlety, confidence and an otherwise impeccable outfit.  Let’s examine probably the greatest example of sprezzatura, Mr. Gianni Agnelli. Look at this picture of Mr. Agnelli in deep thought.  What is peculiar about his outfit?

Look carefully…do you notice his wrist?  It’s more apparent in this photo because your eye is naturally drawn to that area, but it has to do with his wristwatch.  Mr. Agnelli would often wear his watch outside his shirt cuff but under his jacket. 

The trick to successful artful dishevelment is twofold: subtlety and great sartorial know-how.  Imagine meeting Mr. Agnelli.  Would you even notice the watch?  Only if you looked carefully.  And that’s the point: the fashion quirk is subtle and understated.  If Mr. Agnelli didn’t comb his hair or if he wore an extremely wrinkled dress shirt, the dishevelment would no longer be “artful” but simply sloppy.

But even more important is that Mr. Agnelli’s suit is impeccably well cut.  He has great sartorial knowledge and flawless taste—and it shows.  If he wore an ill-fitting suit and a strange shirt/tie combo, people would consider him sloppily dressed.  But because his suit fits him perfectly, he still looks sharp.  That’s the fine line between artful dishevelement and simple sloppiness.

First of all, notice the loosened tie.  Many men do this out of comfort, but they don’t consider how sloppy it can look.  But when Mr. Bastian does it, it looks stylish. Also, notice his jacket cuff.  See the two buttons unbuttoned?  Finally, look his unbuttoned jacket.  There’s a style “rule” that suit buttons should always be fastened whenever you’re not sitting.  Mr. Bastian looks like he’s giving that rule the proverbial middle finger.  You know he knows that rule, but he doesn’t care.  Sprezzatura is as much about confidence and attitude as anything.

I’ll share one more sprezzatura example: Stefano Tonchi.

Take a look at two things: (1) the single button fastened on the jacket, and (2) the part of the collar outside the jacket lapel, but not in a Tony Montana kind of way.  That’s his subtle quirk; what’s yours?

Notice in all three cases the lack of obnoxious wear: well cut suits with no loud colors, and confidence without cockiness.  That’s what separates these three from the average guy at a club on a Friday night.

It’s hard to look like you don’t care when you do.  When it’s done wrong, you have stereotypical “Los Angeles fashion”; when it’s done right, you have Mr. Agnelli, Mr. Bastian, and Mr. Tonchi.  It’s the difference between sloppily bad and eternally cool. 

Style tip? Steven Alan produces a great line of shirts that come wrinkled (if you’ve never seen a display of his clothes, they even hang on the rack at stores wrinkled and creased).  These shirts are a great place to start if you’re trying to get a feel for this sprezzatura.  But the bottom line is that true sprezzatura can’t be done for you and no one can tell you how to pull it off; it’s about feel.  And it varies from outfit to outfit; a wrinkled shirt in one outfit won’t necessarily look good in a different outfit. 

(1) Start with your basic summer chinos.  
(2) Add a basic button-down over a solid colored tee.
(3) Slip on a henley sweater (or a cardigan).
(4) Finish off the outfit with a sharp pair of oxfords.