14 Dead Give-aways You Dress Like an Office Amateur

Dressing for the role is a big part of doing the role. People need to take what you say seriously and credibility tends to sink with each mustard stain on your mismatched tie. Just because you can’t judge a book by it’s cover doesn’t mean people won’t try. Recommended office attire can vary greatly depending on the line of work you’re in or even the season. Most of my advertising friends dress like they’re going to an Ivy League frat party while some of the big firm lawyers aren’t allowed to undo the top button of their oxford dress shirt. There are very few steadfast rules of thumb that don’t carry exclusions. This I can say most confidently: it is always better to be overdressed than underdressed. Why? Because trying too hard is always more respectable than not trying hard enough. (Don’t worry, we’ll teach you the limits too.)

Here’s the first installation of our three part series on guidelines to live by regardless of your office environment or clothing expertise that will move you from the bottom of the pack to the top of the food chain. After all, if you can’t do the role well at least dress like you can.

Part 1: Dead Give-aways You Dress like an Office Amateur

The first part of our office fashion guide is for the beginners – whether rookie, fashion dumb or just historically misled. You don’t have to be trying to impress anyone, just stay under the radar. These are just the bare basic rules of the road. If you can read through this and confidently say you break (almost) none of these rules, congrats, you can graduate to the next level.

1. White socks

They should never see the inside of your office. No one in the history of anything has ever uttered “White socks would look good with that.” You may not believe me, but I actually don’t own any white socks. I’ve gotten rid of all of them and no one has ever noticed.  Black is the new white. (speaking in purely sock terms of course)

2. Brown on black leather

This seems like a basic rule of life like ‘cover your mouth while sneezing’ or ‘thou shall not kill’ yet somehow I see it all the time. Black shoes = black belt. Brown shoes = brown belt. The rule bends a bit for other shoe colors, but for these two it doesn’t budge even a little.

I’m here to kill you.

3. Solid colored shirts other than blue or white

The only solid colored dress shirts you should wear to work are white or light blue. We’re on the fence about light pink so long as it has the right tie. We would extend this to being the only shirts you should own period but perhaps a black does well at night on the weekends. (and only then) This being said, may God have mercy on your soul if you own a red shirt.

(Edit: This is with reference only to the ‘solid’ color shirts one should own. We stand strongly by it. This does not include patterns.)

4. Short sleeved dress shirts

The only guy that has ever pulled this off was a cartoon named Dilbert, and even he has been known to be a bit a whiner.

5. Too long pants

I see this often. Your pants should have no more than one subtle break max and should certainly never come close the floor behind your heel.  (a break is the accordian crumple at the bottom)  You can go no-break which is allowed though it has to be just right or you risk looking like a flood victim. A standard measure is to make sure the cuff doesn’t go past the top of the back of your shoe heel.

This is the farthest his pleated pants could get him.

6. Pants with pleats or cuffs

I put these together as they go hand in hand. The last time anyone was impressed by either of these was 1998. There’s no better way to say “Yes, I shopped at Bugle Boy until recently…very recently.”

7. Jacket size too big

This is one of the more common offenses. If you’re reading this, there’s a 50% chance your jacket is 2 inches too big and you need an inch off your sleeve. Simple rule of thumb: the sides of your shoulder (delts) should show ever-so-slightly, or as close as possible without showing. The jacket cuff should stop at your wrist bone. Anything over and you look like a door to door salesman. You know how they get actors to look so good in suits? They’re tailored to fit every little contour of their bodies. Now you’re two steps closer.

8. Visible undershirts

Never wear a crew shirt with an open collar, that’s what v-necks are for. Get rid of every beater you own.

9. Matching shirt & tie package

Very often there’s actually nothing wrong with the shirt or the tie, individually speaking. The problem is that they succeed almost too well at what they set out to accomplish by actually making you look like guy who bought a shirt & tie combo pack. This leaves people thinking, “Did he buy the $14.99 pack, or did he splurge and go all out for the $24.99 deluxe?”

Some shoes scream, “My step-mom tied these for me.”

10. Square toed shoes

Kenneth Cole Reaction’s cornered the market in the pilgrim-shoe-with-a-massive-rubber-sole department for a long time. Interns cornered the market in owning them. The one upside is that they appear to be indestructible which is coincidentally just as big of a downside. It’s like the tuxedo army boot. Look for something a bit more narrow.

11. Buttoning only the top button of a 3-button suit

Unless you want to look like cholo at a bar mitzvah, it’s the middle button alone (preferable), the top two, or none at all. Better yet, avoid the conundrum all together and stick with 2-button suits.

12. Brown shoes, black suit

This is the true sign of someone trying to punch above his weight class. I’ve seen two people pull this off and both of them had clearly spent a ton of money on the ensemble and seemed to have exquisite taste to back it up. It’s unlikely you’re one of these guys.

13. Symboled Belt

A dead give-away of someone who has no idea how to dress fashionably is someone who thinks looking like an advertisement replaces it. Even the real ones tend to look like they were made in Chinatown. Simple belts have never gone out of fashion.

14. Too long or short tie

I don’t care if it takes you fives times to get it right. The recommended length from your dad is just down to your belt buckle which is about right for wider ties.  If you have a slimmer tie, just above it – we’re talking a centimeter – is the way forward. This also helps when you loosen it on your neck later in the day and it won’t go down to your fly.


Now that you now what to avoid, our forthcoming edition will tell you what to go after. Follow us on Twitter or Like us on Facebook to be the first to know when it’s up. (or just go to the site every day like you should be doing)