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Dressing sharp in an ultra-casual environment

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    Dressing sharp in an ultra-casual environment

    Hi guys,

    As I mentioned in my earlier post, i'm relatively new to fashion. One of the reasons it is so, is that I come from a very easy going country. I mean,evenlawyers hardly wear suites here, and in most buiness occasions, an oxford shirt will suffice. Flip flops are an immensly popular streetdress here, as well as printed Tees and undershirts, Crocs shoes and cargo pants. The sharper lookin guys I see usually go with sneakers, dark jeans and some sort of casual shirt. I saw the "looks you liked" thread, which are precisely what I like, but I fear they will look weird, because even a sports jacket is uncommon here. E.G. I just bought a blazer, and the chest pocket isn't a real pocket (The same happened as I tried on a suite-jacket). And even the most luxurious suite stores don't sell pocket squares! So how am I to dress sharp on an everyday basis, without looking funny?


    Fit, fit, fit, fit.

    Make sure it all fits perfect; that means slim fitting, possible alterations, etc. Take a look at what fits and start by taking one piece and bringing it to the next level. So if everyone is sporting cargo pants, bump up to chinos, but keep the rest what everyone else wears (except the fit, make sure it fits perfectly).

    This way you don't look out of place, but still look great. Also, keep in mind this is also about your confidence. If you feel out of place and odd, you're going to be perceived that way.



      The chest pockets are probably functional, they are usually just sewn shut. A seam ripper or small knife (carefully!) should open them up easily.

      And you can make a pocket square out of pretty much any fabric. Just search the net for some ideas.

      If you want to stay casual, the most important thing is fit. Jeans and a shirt can look either extremely sloppy or extremely put together depending on how the pieces fit. Find some things you like, make sure they fits well -- not to baggy or long -- and rock it.

      Also, get a cool watch or something.

      My friends give me shit all the time for dressing differently than them. Not like I'm wearing 3-piece suits everywhere, but these guys wear workout gear out to bars. Under Armour and such...

      Out of curiosity, what country is it?



        Thanks for the advice!

        It's Israel.



          I feel your pain. I work in an industry (wildlife biology/conservation) and office where you're actually frowned upon if you "care too much" about what you wear and people do most of their clothes shopping at places like REI, North Face, Patagonia, etc. (not that ALL clothes at those place are bad). Part of that attitude comes out of the eco-conscious and "consumption is bad" mindset that many in my field subscribe to. Not that I disagree with many tenets of this philosophy, but I think many people just get carried away with it (especially here in the Bay Area), especially when most clothes made by outdoors clothing companies aren't even made in the US (hey, if it's organic cotton, who cares?). Like you, I'd get made fun of in my office for wearing something as simple as a blazer or sport coat with an OCBD and chinos (e.g., "geez, are you trying to look like a banker or something?").

          I agree with and try to follow John's basic advice of simply wearing jeans and casual shirts (OCBD, patterned) that fit really well (a challenge with my body type) and shoes that aren't too casual but not too dressy, either. I've found that my Clark's desert boots and Cole Haan Paul chukkas (which are 10 times dressier than what most guys here wear) are well-suited to this.

          But yeah, unlike most of my co-workers I somewhat envy guys who get to wear suits and/or dress nice for work every day. I love most of the looks in the WIWT and "Looks that You Love" threads on here but it just isn't an option for me given how casual both my workplace and the Bay Area culture in general is.



            Hi Matt,

            It's pretty much the same around here. My personal analysis is that the mandatory military service at the age of 18 for 3 years, the informally mandatory long trip abroad afer the service and relatively late college era keep people in the "Teenage mode". To that, you might add the inherent informality you can see throughout the Israeli history and culture and the heritage of a society comprised of small towns and agricultural settlements, not to mention the very hot weather.




              You said the pocket isn't a real pocket on a jacket that you bought? I you sure it's not just sewn shut? Most suits and sportcoats are sold that way.



                @Matt: Everyone else in my department wears sneakers and untucked polos. I just wear suits and sportcoats because I want to. There's a lower bound for the dress code, but no upper bound. I caught jokes for a few weeks, but they got over it. We're all friends so it's all in good fun. Now nobody really gives it a second thought anymore.



                  Dress well and dont care what others think too. I was the only guy on a plane in a 3 piece suit...I worked it with a smile!

                  Same thing about work, people were like wtf now if i dont dress well they ask if im ok, generally guys make the joke comments, women tend to encourage the well dressing.... Im not into dudes so it works well



                    Hi Allan,

                    Well, I just cecked - the blazer doesn't have a pocket whatsoever. I guess I should be optimistic and believe that in the suite-jacket's case it is indeed just swen shut :-). You are correct about the "no upper bound'.

                    Shadow4life - The "Not into guys" advice is solid. We shouldn't care what guys think.

                    Matt - In one of the offices I worked in, 40 year old high-ranking guys came with printed Tees and running shoes. Whenever I put on a buttoned shirt I'd get stares. The problem is that in many a workplace, some sort of conformity is still expected, even if it's for underdressing.



                      Resurrecting this to show just how casual my office is. Upon walking into my boss' office (who is also the Treasurer of the entire company) wearing dark blue Levi's and a lavender OCBD (from JC Penney) under a dark gray merino V-neck sweater (BR):

                      Boss: "Wow Matt, you're all dressed up!"

                      Me: "But I'm wearing jeans."

                      Boss: "Yeah, but with that sweater and shirt you look all ready to take the kids out Christmas tree shopping or something."


                        "I'm here to take your job"

                        that's what you say!