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How to dress up at a dressed down workplace

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5 Ways to Look Good in a Casual Work Environment

Top Photo credit: WBAIV

He, wearing pleated dress pants, a traditional fit dress shirt, and wide iridescent silk tie:
“Why are you dressed so nice all the time?“

Me, wearing jeans, a tailored button up, and an Old Navy sport coat:
“What?“

The current state of most workplace dress codes seems to fall somewhere between non-existent and go-kart track.  And frankly, that’s awesome.  Not everyone feels comfortable in traditional dressed-up work clothes.  And the only thing worse than a cranky co-worker is a cranky co-worker in pleated microfiber pants.

But while they smile through their 9-5 in bowling shirts, Lees, and Avias, you’re stuck trying to figure out how to look the way you want without showing up overdressed.  It’s not easy, because you want to be at ease without putting your colleagues on edge.  Here’s how to express a little personal style at your job, without going over the top:
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#1 Casual Brogues: Allen Edmonds Elgin – $236 ($295) | Sebago Brattle – $65* – $101
The leather and the sole ease them down to casual.

Brogues and wingtips were originally intended to be tough, hard wearing shoes that weren’t worn for dressed up occasions.  That’s no longer the case, but there are plenty of dressed down brouges that’ll work extremely well with denim.  Look for less shine and a lighter contrasting sole. Reader MNPilot brought up the A.E.’s over here, and the Sebagos have been featured before.  Both currently 20% off at Endless, no code is needed, and they come with free 2-day or overnight shipping.
**UPDATE** The Sebagos are available for a ridiculous $65icon (in black and taupe suede, not the tan) on the very much appreciated sierratradingpost.com.  You’ll need the code ALVAPRIL1 for the final discount.  Expires 5/4/11.  Big credit to BobMighty in the comments.

 

#2 The tailored cotton Sportcoat:  J. Crew Cotton Blazer – $148 | CK Cotton Blazer – $119
Both over $100, but there are cheaper options.

Death, taxes, and us here at Dappered endorsing the well tailored cotton blazer.  Navy, black, grey, khaki, striped, gingham, whatever.  Just make sure you get it tailored so the end result is that athletic V shape.  And skip the t-shirt under the blazer look.  It’s too clubby for work… and pretty much everywhere else.  Including the club.

 

#3 Embrace the Wrinkles.  Iron Less.
The dryer ironed it.

You can’t escape the word rumpled in men’s style.  So embrace it.  Don’t starch the life out of your shirts when most of your male colleagues think of golf when they hear the word “iron.”  The blazer will hide the wrinkles anyway.

 

#4 Knit or cotton ties:  TheTieBar Silk Knit 2″ Tie  – $15.00
Trump would not approve. Which is good.

As long as you’re working somewhere casual, they can absolutely be worn year round.  They’re not all slicked out like a standard boardroom silk tie, and they also keep your collar under control during the day (I know, shocking).

 

#5 The Rubber Band Watch: Victorinox Alliance Chrono – $176 ($300) | BOSS Chrono – $295
Wear your rubber proudly.

You don’t have to be a certified SCUBA diver to wear a watch with a rubber band.  It transforms a dressed up dial like either of the two above, to something that could be worn all the way down to a t-shirt and jeans.

Any other ideas for dressing well at an ultra-casual workplace?  Leave those in the comments below…

Comments

  1. Great post Joe! Did not disappoint after the hype 😉

    I agree–especially as somebody younger (20) it’s a bit of a challenge. You don’t want the “why are you so dressed up” comments (as addressed in your how to take a compliment post a few days ago), but as we all do on Dappered, I dress for ME, and me alone.

    For me it boils down to three key factors: fit, consistency in dressing, and “standing out quietly”, which is obviously hard to quantify. Embracing a bit of colour, keeping the “balance” right of the whole outfit while working in a few stand-out pieces is always tricky, but achieves this.

    I love the watches–very nice examples of toeing the formal/casual line.

    I must admit that I always end up ironing my collars even for casual “rumpled” shirts… personal pet peeve, but I think they have to be as crisp as possible.

    And that bowling shirt, lees and avias outfit is truly shudder-inducing to imagine together… Not to mention the rave reviews all three pieces get!

    Keep it up–great as always.

    Cheers,
    Ben

  2. Great post, Joe. Unless one is a lawyer, this is something that the majority of the readers of this site will encounter at some point in their careers.

    The best advice I ever received on this subject was to dress to the same level of formality as your coworkers, but dress well at that level of formality.

    Application of this advice is in line with Joe’s example. If you work in an environment where dress shirts, ties, trousers or jeans are required, then wear fitted dress shirts, fitted chinos or jeans that will last, and maybe a knit tie. Similarly, if you work in a “t-shirt, shorts, and flip flops” environment (like I do), then you wear fitted polos, chino shorts, and some nice sockless dress(y) shoes. These examples illustrate standing out from the crowd without being pompous.

    I’ll close out this already long comment with a story: At my first job out of college, I wore a dress shirt and dress trousers to work everyday. Everyone else was rocking t-shirts, jeans/shorts, and sandals/flip flops. I was having kind of a hard time making friends. One day, a coworker pulls me aside and very politely tells me that my level of dress is a bit off-putting. He wasn’t a jerk about it, just trying to offer advice to a fresh grad. I started dressing more casually but still dressing well, and sure enough I started connecting with my coworkers a bit more.

  3. An excellent philosophy. I full-heartedly agree.You’ll still stand out, but in the right way!

    Cheers,
    Ben

  4. I work at a digital marketing firm where sweatpants are the norm. I will say that ruffled shirts and casual wingtips have been saviors. I can dress up and look like an honest to god professional without getting the “what, are you meeting a client today” comment.

    Next step – knit ties. Great post Joe! Now to order those Sebagos…

  5. Killer post! I work where suits are the norm. But I love reading about this stuff for the day I can get into a more relaxed environment.

  8. Those Sebagos. Any feedback? I like the black ones and would they look right with chinos or grey Khakis? By the way, love this site and have made some sweet purchases. Thanks a million!!

  9. Excellent post. I’m a PhD student, nearing the end of my degree and work in an Academic (scientific) environment. Over the last year I’ve been “upping” my personal style but trying not to overdress. A blazer is actually pushing it around here most of the time, but paired with jeans instead of slacks and it works well. I started out going a little over the top ultra traditional (but was getting plenty of compliments) but have no transitioned to a more “dressy” casual look that is really working well.

    Great post!

  10. Really glad to read this one. I work in a “business casual” (aka go-kart track) office and this was so helpful. It also proves that to acheive that “sort of dressed up” look, you gotta spend the dough. C’est la vie.

    But yeah, this has got to be the best post I’ve seen on Dappered in a while – this is like a throwback post to 8 months ago. Thank you so much.

  12. I really don’t worry about the “why are you dressed up comments”, people who make them are not up on their game, so they can’t relate to yours. As dapper men, we’re in the minority.

  13. I really don’t worry about the “why are you dressed up comments”, people who make them are not up on their game, so they can’t relate to yours. As dapper men, we’re in the minority.

  14. “this has got to be the best post I’ve seen on Dappered in a while”
    Agreed. I’d like to see more tips/suggestions and less straight product reviews.

  15. I was going to say something similar. If I was at an event that was officially labeled “casual” – whether that be a self-described casual work environment or a get together – and someone wore a tie (knit tie or not) – even if they look great I’d still think they didn’t dress according to the occasion.

  16. Definitely, although there is a balance you can do to make tie wearing casual. Leave the top placket button undone on the shirt collar and loosen the tie knot (especially with a knit tie). It’s a bit of an affectation, and one I haven’t attempted, but I’ve seen it done successfully before. Especially if it is paired with jeans and a casual leather shoe of some kind, like those pictured in this post.

  17. Yea definitely see that. I’m a lab tech at a major university so I assume we have very similar work environments. Do you wear leather shoes to the lab?

  18. I do. I should note that I do Computational Biology so there are no real concerns about spilling reagents on them or anything like that, and as a student I don’t have expensive shoes anyway. But even if I was doing benchwork I would wear leather shoes in the lab anyway, as long as they didn’t have too slick of a sole.

  19. But what if they are your supervisors or managers? They might think you’re having an interview for another job. I get those comments all the time…

  20. Nice find on those Sebagos. This is a great post. I’ve been trying to find balance between how I want to dress and how people dress at my job.

  21. So what if you were having an interview?? What you do outside of company time is none of their business!! Besides, would you tell them if you were??

  23. That’s incredible. NICE catch. Sierra Trading Post… man do they get it good sometimes. Updated and credit given. I’m showing the code doesn’t end till 5/4 which is pretty sweet.

  24. Thanks. I found it when I was disappointed endless.com ran out of my size. Thank goodness for Google Shopping and retailmenot.com haha.

  25. Just sent out an APB over Facebook and Twitter in case anyone bought the Black or Taupe Suede yesterday. I’m sure Endless will let them cancel their order (or, since shipping is free, they can just send them back.) With Sierra Trading Post had those in the British Tan. Crazy find. Thought I had scoped out the net for anything cheaper and couldn’t find em’ anywhere for less. Again, great catch. Those are slick.

  26. One thing I did notice is that on endless is said the shoes come from the Dominican Republic, and on Sierra it said from China. But i haven’t found anything online to suggest either site would sell fakes.