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Our second article on how to dress for work will focus on what to do after getting the basics down and onto how to fine tune the details. In the movie Crazy, Stupid, Love, Ryan Gosling’s character gives fashion advise to Steve Carrell: “Be better than the Gap,” he tells him. I have no quarrels with the Gap to be honest but I like the speech. Don’t settle, reach further, and be better when you can. 

The first part of our series on what not to wear in the office was fairly well received. A few reddit users noted that any fashion rule can be broken if done appropriately. We tend to agree with this, there isn’t a rule in the world that cannot be broken or least bent a little under the right circumstances. That being said, those were the most basic and least likely you’ll get away with breaking. Most of them I’ve never seen anyone pull off ignoring. These next rules will be much less written in stone but still fairly standard. It’s not about spending your life savings on the perfect wardrobe, but making smart choices and knowing when drop an extra couple bucks where it makes sense.

The Shirt

The Fit: It’s difficult to get a good fitting dress shirt in this part of the world. American made shirts tend to balloon at the waist with sleeves resembling the fit of a windbreaker. A well fit shirt shouldn’t feel like it was draped over you but cut around you. You shouldn’t be able to fit more than two fingers in distance between your neck and the collar and the sleeves should sit just beyond the wrist bone with your arms hanging. H&M has a surprisingly strong line of relatively slim fitting shirts in mostly favorable patterns at $40 a shirt, even $30 if there’s a sale. A second option is to take a favorite shirt to a tailor and have the sides taken in which will set you back about 20 bucks. Avoid the dry cleaners and look for a pro. Try it once and feel the difference. If you haven’t worn a slim fitting shirt you don’t know what you’re missing.

“Hi, I’m from the year 2004.”

The Style: There’s a lot more collar styles than you think. A tailor I went to showed me no less than a dozen options. From this to this and everything in between. I’ve seen a few articles recommending the collar by the size and shape of your head but I don’t buy into it. Shirts with a wider (“spread”) collar provide a subtle flair to help you stand out without going overboard. It will give you a lot more play with your choice of tie knot and less like an extra in Goodfellas. Splurge by spending $4 for package of extra collar stays and be sure to replace them the moment your collar shows any sign of curve. (aka the Flying Nun) French cuffs – or double cuffs if you’re British – work well when supported by a decent pair of cuff links and you can still be casual going tie-less with them.

The Color & Pattern: The first article mentioned that the only solid colored shirts one should wear to work are light blue and white. This ended up being one of the most hotly contested rules but we stand by it. We’re taking a stand against all pastels, blacks and particularly any shade of red. That being said, the world is your oyster once patterns come into the mix. A safer bet is to stay with lighter colors and no more than two or three per shirt. Go easy on the multi-colored striped shirts. Express seems to love these and so do people who shop at Express. Be better than Express. The stripes on shirts should be subtle and thin, but with check – as in checkered – you have a lot more leeway. Gingham and plaid are types of check that tend to have smaller and multi-colored/dimension checkers, respectively. Thomas Pink, who makes great but expensive shirts, has a good website to browse shirt types.

The Tie

The Color & Pattern: One of the first tie rules people tend to bring up is the use of the “Power Tie,” the bright red tie showing everyone who’s boss. I’ll say this; if you have to relie on the color of your tie alone to demand respect you’ve got bigger issues than clothing. Ties are the trickiest to describe of anything else here as much of it depends on the shirt. I could easily write an article on this alone. (as others have) For majority of the items we discuss money can buy most of your way into style but choosing the right tie is left up to the thinking man. One of the more standard rules is to have a standout tie or a standout shirt but not both as it can seem cluttered, though there certainly can be exceptions. Another truism is to make the tie match the outfit, not the outfit to the tie. If you absolutely have no sense of matching ties then you can use sites like this to figure it out.

It’s best to have a good mix – diagonal stripes, (small) dotted, check, solid and even paisley – and definitely more ties than shirts as it’s much more noticeable when you have to recycle within a week (not that it’s recommended) or if the same shirt always gets the same tie. In time you’ll get used which ties go with each shirt.

The Width: Stay clear of the wide tie and go a bit thinner. This one’s easy but you should also have a slimmer fitting shirt to pull it off. We don’t recommend going full hipster skinny but the days of 4 inch wide ties have gone. Have it slightly shorter, above your belt buckle but within an inch.

The Knot: Know how to tie at least two knots, but three is too simple to learn not to. Here are the the three most basic; Four-in-hand, Half-Windsor and Prince Albert.  (though I did have to look up their names) Some people have taken to the Full-Windsor which, frankly, is the easiest way to look gaudy. It might be worth knowing if you have a tie made with thin material and a wider collar, but use at your own risk. Simply put, thinner collar widths get thinner knots. A wide collar can get a skinner knot but a thinner collar shouldn’t have the full opening taken up by the knot.

The Suit

The Fit: We cannot stress how important a well fit suit is. Look at the side-by-side below. You can have a lot of minor alterations by a tailor but one big fix one can distort the shape and designed. Tailors can take in (make smaller) but it’s ill advised to take out. (expand) It starts at the shoulders which should never hang over your own, perhaps even slim enough for your delts to make an ever so slight impression. Be sure the pant bottom isn’t too wide, 8 inches across when flattened at the cuff and the length should hardly rest on top of your shoe if at all. The jacket cuff should end at the bumps on your wrist while hanging down – showing a half inch of cuff – and the jacket shouldn’t go below the bottom of your rear. Lastly, you should be able to stick your flattened hand inside of your buttoned jacket, thumb on your chest and pinkie against the top button, and have little to no extra room.

The Style: For me, it’s always a two-button, double vent. (those are the slits in the back) Nothing wrong with single vent but everything wrong with no vent. I wouldn’t yet say three button suits are out of style but they’re at least a bit dated at this point. Better put, a three button may at times look as good as a two button, but it will never look better. Common advice is that they’re better for taller people but Lebron James is 6’8″ and he’s usually in a two button. Excuse that he’s got both buttons done here – it should just be the top. Perhaps huge people should just get buttons the size of steering wheels instead. (Just kidding…but really, how awesome would that be?) Every year GQ puts out an article that says the double-breasted suit is making a come-back and shows some model sporting a $2500 Versace and even he barely pulls it off. You don’t have a chance. It’s dead. Forever.

The Color: Navy blue is the first go-to followed by either a charcoal or grey. Lately I’ve been hearing a lot that solid black suits make you look like a waiter or you’re attending a funeral. I certainly have felt this way about many but I think it’s way overstated as our friend above proves. It’s all about the fit here along with the right shirt & tie. Pinstripes should be very subtle or you risk looking like an old time mobster.

The Shoes

People notice your shoes more often than you think and they will stand out greatly when you want them to. I must say that with all the previously mentioned clothing pieces it’s not too difficult to be a smart shopper and get away with a cheaper option. Unfortunately with dress shoes it’s much harder to get away with. ‘You get what you pay for’ strongly applies here. Whether you have one pair of shoes or 10, your first pair should be basic black oxfords with leather soles. Cap-toe works as well. Choose one really good pair over three decent ones. Smartly spending three times as much will have equivalent impact on their look and duration. You can wear them every day and they’ll last years with the proper care. For starters, the first thing to do is put on a pair of plastic heel taps, probably toe taps as well, which cost a buck a piece to put on at a shoe store and will significantly slow the wear. Once you’ve worn it down, re-soling a shoe can be expensive – in NY as much as most people’s new shoes – but it’s worth it if you bought the right pair. You can save by just re-soling the top half if necessary, but the whole shebang including heels can set you back $50 to $80. Use a personal polish stick/sponge every 5 to 8 wears and get professional shine every month. Lastly, every decent pair of shoes you own should get oak shoe trees. They’ll preserve the shape and deter the smell.

Next week we’ll be adding our third and final installation to this series with a few tricks on how to truly stand out.

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