Dress for Failure

You’ve read the “dress for success” stuff, right?  You know the top 10 things you need to do to dress for success, for an interview, network event, one-on-one meeting, etc?

Well, I am absolutely, 100%, categorically not qualified to write a post on how to dress for success.  But I figured I could write a post on how to dress for FAILURE. Please understand that my younger brother got the gene to know how to dress for success.  I got the gene that makes me socially backwards.

One thing I should note, the more offensive things (like #1) are not expensive to fix. I realize if you don’t have the cash to dress appropriately, you are stuck between a rock and a hard spot, and even Will Smith in Pursuit of Happiness pulled of an interview in horrible attire.  But please, don’t break my #1 rule below 😉

Top 10 Things a Guy Can Do To Dress For Failure

  1. Wear white socks with your suit pants. This really is the funniest combination I’ve seen, and continue to see.  In all age groups.  I’m not too surprised when I see a 13-year old kid with a suit and white socks… but when I see an adult sport the white socks I wonder if this is the only time they are wearing something other than jeans or shorts in this next five years.  My favorite dress socks are either black or dark gray.
  2. Wear Dickies pants. These are work pants.  If you are trying to impress someone, and this is your idea of dressing up, you probably ought to be applying for a position where you need to wear a hard hat.  If it’s an office spot, Dickies looks like interesting jeans, and I doubt you’d interview in Jeans (even really nice, overpriced $250/pair jeans).
  3. Don’t align your GIG-line. This refers to the line that your shirt buttons and pants zipper make.  Imagine you take your shirt, and pull it far to the side, so if it were to keep going the line went to your foot, instead of straight down the zipper.  The zipper and the buttons should align in one straight line. (thanks to Jonathan David, whom I dined with in Silicon Valley, and his Navy training, to set me straight… it is not a jerk line, it is a gig line… you can see a bunch of results on a google search for gig line)
  4. Tie your tie so the front, fat part is HIGHER than the back, skinny part. I was taught your tie (the front part) should fall a few fingers below your belt.  Not higher than your belt, and not much lower.  Definitely NOT higher than your belly button.  Bonus, have the front fat part higher than the back skinny part. My seven year old son has to tuck the back part of his tie into his shirt, because the tie is to long for him… but the point is, the back part is supposed to be out-of-sight.
  5. Wear your pants too high or too low. No waders… I don’t really want to see your socks when you are standing.  And, don’t let your pants hang below your hips, like you just got back from the skate park.  I’m not interested in seeing your boxers, or tighty whities.
  6. Wear a short-sleeved shirt with a suit jacket. No problem… until everyone takes their jacket off and you want to, too.  It just seems stupid.  Maybe I’m wrong on this one… but I’ve been embarrassed when I’ve done it.
  7. Wear a brown belt with black shoes. Your shoes and belt should somewhat match.  Black goes with black, brown with brown, etc.
  8. Walk into the room with the back of your shirt untucked. I’ve seen this happen when someone has been working, bending over, or just getting out of the car.  Before you are “on,” check to see you are tucked in nicely – all the way around.
  9. Don’t wear a full undershirt. I don’t want to see aspects of your body through your white shirt.  I’m not talking about those sleeveless undershirts, I’m talking about a white shirt that looks like a t-shirt. NO LOGOS, or other artwork, either!
  10. What’s your number 10?  (or number 1)?

I’d like to do a Top 10 Things a Woman Can Do To Dress For Failure, but I only got three.  What are you Dress for Failure tips (for men or women)?

30 thoughts on “Dress for Failure”

  1. Other men tips: Wearing sneakers, even with business casual is a Dress to Fail!

    As for women: (1) It’s ok if you want to wear sexy undergarments to work, it’s NOT ok if everyone else can tell you’re wearing them. (2) flip-flops. (3) Ill-fitting clothes – too tight or too loose gives two very wrong impressions.

  2. For a woman – dressing to show you mean anything BUT business. This includes looking like you just rolled out of bed, that you’re cruising for a date, or that you forgot this was an interview instead of a poolside rendezvous. No plunging necklines, micro minis, or see-through ANYTHING unless it’s an overshirt with a nice FULL COVERAGE top underneath, not a camisole.

  3. 10. Don’t wear aftershave. Some people are highly allergic to fragrances, perfumes etc. I know this isn’t “dress” per se, but this can be a show-stopper if you have an important meeting or interview. Jason — same goes for women. So you can add that to the Top 10 list 🙂

  4. For people who has glasses:
    10. Stained & slanted glasses: Since most people will be looking at your face when you talk, so your glasses is just as important. Wipe off the stains/spots & make sure it’s not slanted at an angle.

  5. Some items for the ladies top ten:
    – too much makeup (a wise lady told me when I first started wearing makeup is to make it look like you are not wearing any)
    – too much jewelry, bling so to speak (too much glitz and glam is not good in a professional setting, it’s work not the Oscars!)
    – “jersey girl” hair style ( I’m an Italian New Yorker and my cousins are all about the big hair. Tame it down when in a professional environment.)

    Side note on the white socks with dress shoes, I could not agree more!
    One to add….please match! Drawing on personal experience, I’ve been embarrassed by family members who can’t match to save their lives. I’ll never forget my grandfather wearing maroon pants, a red sweater and a pink collared shirt underneath. When I commented on his attire, he told me they were all shades of red. Not good!

  6. #10… your socks should match your shoes, not your pants.
    #11 EVERY man should have at least two french cuffed shirts and some niee cufflinks.

    good refresher Jason, as the CEO of a self-improvement and leadership org i am constantly having to review and remind people about some of these very, very simple and basic steps to looking your best.

  7. No stains. With ‘tide to go’ in every attache case, desk drawer, and your car glove box. No coffee waiting for an interview. Some how I always drip something.

    Now if I can just remember to take off my bib before I leave for the office.

  8. 10. Forget about shaving.

    Going into an interview with 2-3 day stubble is a sure fire way to dress for failure. Now, if you have a late afternoon interview and your 5 o’clock shadow is coming on, you can probably get away with it. But if the person interviewing thinks you’re trying to grow a ‘stache, you’d better make sure you’re interviewing for a police or fire department job.

  9. Put pleated pants in the box with your grandmother’s photo albums.

    Stay out of Tommy Bahamas.

    Invest in your shoes.

    Pant cuffs are lame.

    Hem your pants with enough break so that you don’t look like you are preparing for a flood.

  10. I just posted the Dress for Failure for Women, today!

    I sincerely appreciate your input on these things…

    @Tracey and @Diane – thanks, your stuff made it into today’s post for Dress for Failure for Women 🙂

    @Rich – agreed! But I have small hands and wrists and jewelry looks dumb on me.

    @Mary – excellent points for women… I like how you put it!

    @Tara – Totally agreed… I’m not allergic but I am very sensitive to smell.

    @Ian – one of the things in my pocket is my glass cleaner… I hate not having it, and wonder if people can see me sometimes through their dusty or spotty glasses.

    @Jenna – on your side note… that is SOOO funny… !

    @DMX – excellent point on socks matching shoes, not pants. I forgot that one.

    @reinkefj – you always crack me up. No stains. No bib.

    @John – yes, shave, please. And floss, while you are at it.

    @Carolynn – I beat kelly to it 😉

    @Robert – excellent. I’ve been eyeing a pair of shoes, just not ready to make that investment. But I know I should.

    @Jonathan – THANK YOU. I didn’t think jerk line was right… !

  11. A tip for both men and women: NO HICKEYS! I once interviewed a person that had every single quality that I was looking for but I could not get pass the hickey on her neck to hear what she was saying!

  12. How about ;earning how to use an iron. I once interviewed an attorney whose suit literally looked as if it had been wadded up in the hamper for a couple weeks. The best bet before you interview, drop everything you are going to wear at the dry cleaner. Honestly, I would rather see an interviewee in slacks and a blazer that look sharp than a wrinkled suit that is holding over from the late 70s.

  13. For #9, I think you meant to say to wear a v-neck shirt under a button-down, as the o-neck (or whatever it’s called) would show through the top of the shirt.

  14. Before I begin…I agree with Robert Payne and @dmx’s #11 point.

    Now as for me…
    1. The socks –
    I am more on the stylish side of dress and have worn various colors of socks with my suits, while meeting clients, and have never been denied the work. However, not everyone can pull it off OR maybe they just weren’t able to see the colors of my toes! lol

    2. Dickies –
    No MAN (over 25 yrs) should have a pair of dickies unless he works on an assembly line, as a mechanic, or in construction…even then, most of them wear jeans now.

    4. Tie end –
    I am a GQ man and they say to let the tie point end no lower than the bottom portion of your belt buckle. However, depending on your height will the length differ.

    5. Pant height or lack thereof –
    Robert Payne said it best…see above.

    6. Short-sleeve –
    This remedy is only good for women. Men should never, unless in a casual dress environment, own a short-sleeve button down shirt. Even in a casual environment the shirt should be shot and hung for all as an example of bad clothing choices. ONLY children are allowed to wear these shirts, for holidays and no other…lol.

    7. Black w/Brown –
    Now, I wear and have worn black w/brown on several occassions BUT I also have many shades of brown that work well with my any of my black shoes (my wife enjoys that I have more than 3 pair of black shoes, lol, women will get that quicker). Again, if nature can pull off colors in any way then so can I…ONLY with the effort of much more work because I didn’t create nature but I have to create my look.

    8. Shirt back untucked –
    He set himself up for that one, I feel when my shirts are ‘out of whack’ and not how they should be.

    9. Undershirts –
    This one can vary based on the person, style of dress, and level of perspiration.
    A-shirts (slang, wife beaters) are perfect for a thicker, more expensive, and well made dress shirt.
    T-shirts: good for those persons like me, I sweat alot and it absorbs the excess so I don’t have a wet underarm when I do remove my jacket.
    No-undershirt: ONLY can a well made, thick dress shirt allow for this to be done and if you do not perspire much.

    10. Clean SHAVEN!!!!!! (no need for elaboration)

  15. I have a long time friend who has worked in human resources for at least 25 years. He says this story is absolutely true.

    He was interviewing job applicants one afternoon when a male candidate walked into his office cross-dressed as a woman. He had everything — a very short dress and a low cut top, but it was quite obvious he was a cross dresser.

    Oh, the guy did not get the job by the way.


  16. For men or women, if you are wearing socks, if your pants ride up at all when you sit or you feel comfortable enough to ‘mirror’ someone who has crossed their legs, your socks should not reveal skin or hairy legs!

    Also take note of the what the people in the office are wearing; it will give you a good clue as to what to wear to a follow-up interview or even the first day of work assuming you are hired. A good recruiter will also give you clear guidance on the dress code in advance, in case it is a more creative environment where you may show a little more flair.

    Wear a color that makes you seem alive! I am so fair-skinned I cannot wear pastels; they make me look
    ready for the undertaker!

    And even if it is Casual Friday, unless told to do so by the person interviewing you, show up in business attire… it is a sign of respect.

  17. Great post and comments. I agree with everything except that I don’t quite get the objection to pleats. They can add a subtle note of distinction, in my opinion. (Just make sure the pants fit well, which you’d do anyway, right? Pleats stretched out because they are too tight don’t *quite* give the effect you’re looking for.)

    I’d add that in some settings — academia, libraries, probably museums and nonprofits, to name a few I’m acquainted with — a mustache or beard is fine if it’s well-groomed and doesn’t look goofy. (I can pull off a beard but not a mustache by itself, for some reason.) But please please please, either shave or don’t. That ubiquitous two- or three-day stubble look is like the Harpo perm so many women were wearing in the late 70s — there are probably six or eight individuals on earth who can actually wear it well. (Actually if you have a beard you’re still going to shave around it. I can’t imagine a jacket-and-tie setting where a neck beard wouldn’t look grotesque.)

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