How to dress up at a dressed down workplace

5 Ways to Look Good in a Casual Work Environment

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

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 $65 (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

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.

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

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

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…