From the Mailbag: Dressing well at work without looking stiff
My workplace has a fairly business casual policy for most employees. I just found out that I’ll be serving in an interim role that will raise my level of responsibility. As a result, I’m thinking that I may need to adjust my style which leans more on the casual side of business-casual (Dress shirts, sweaters, Timex Weekender, Dockers D1s). The higher-ups generally wear suits to work each day.
However, I don’t want to suddenly start showing up in suits that would turn the heads of those who have worked with me for years. What would be the key pieces for a “higher-level” style? I know just the dress shirt and tie look isn’t recommended, but that’s my initial thought for a middle ground.
– Luke
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Congrats to Luke for the promotion. Here’s to hoping the situation is ripe for that “interim” tag getting removed once he shows his superiors how valuable he is handling the new responsibilities.
Luke makes a great point. The cliche is “dress for the job you want,” but y’have situational awareness too. Ike said: “Leadership is the art of getting someone else to do something you want done because he wants to do it.” Fair or not, going from khakis & polo to three-piece power suit overnight might be off putting to those who didn’t get a promotion. Here’s a few key options for Luke when it comes to ratcheting up his office style without going crazy.
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#1. Non Plain White Dress Shirts + Casual Ties and Tie bars

You can still wear a shirt & tie but look casual and streamlined. Leave the stark white dress shirts on the hangers, and stick with light blue, or better yet patterns like checks and gingham. Try solid color knit ties. Cotton or wool blend ties work too. Steer clear from super glossy looking silk ties. A tie bar keeps your tie in place and thus, your lines clean. Make sure your shirts are tailored. Roll your sleeves up the right way. And see Adam Scott’s character Ben Wyatt on NBC’s Parks & Rec for the overall look. He sticks with a lot of plaid, but it works.
#2. Cotton Blazers + tieless: B.R. Tailored Fit Cotton Blazer – $198 (but on sale a lot)

Jackets man. They do wonders. Skip anything wool and real formal, and opt instead for cleaned up cotton blazers and sportcoats. You can wear these with a simple button up shirt and chinos (or dark denim if your workplace is that informal) till the cows come home. Or Kingdom Come. Or, well hell, whenever, but you’ll look good when it happens. Why no link? They were selling these online for, if memory serves, $198, and they had just been added not too long ago. Plenty of sizes too. But they’re gone. They do seem to be carrying them in-store, so check there. Why the sudden disappearance online? Not sure. It vexes me. I’m terribly vexed.
#3. A ridiculously clean, simple watch: Bulova 96B104 – $77.95

Why wear a watch when everyone has a cell in their pocket? Because a watch says: “I have enough going on that I need to know what time it is, but I’m also not married to my phone. You can’t get a hold of me whenever you damn well please. Sometimes, people have to come find me.” Facebook and Angry Birds can wait. Smart phones are like cats. Who owns who is always in question. A watch like this, even for as cheap as it is, is all business.
#4. The non messenger work bag: Bosca Slim Brief – $196.90 ($395)

Here’s the brutal truth. Messenger bags, as convenient as they can be, often look like you’re transitioning between that Jansport you wore in middle school and an actual briefcase. You want something with handles. Not just a shoulder strap. If you bike to work, then all bets are off. Otherwise, get a briefcase. Doesn’t have to be a hard sided attache, but you want something that doesn’t make you look like you’re about to hop on a segway and deliver a sandwich to some stoner holed up in his apartment. Examples over here.
#5. A once every three weeks haircut (or about there)

Everyone’s hair grows at a different rate, but you want a haircut schedule that prevents people from saying: “You got a HAIR cut!!” once you get back to the office. A trim every three weeks should do it for most. Once a month can be pushing it for many. Keeping your hair from crawling down your neck/spilling over your ears makes a big difference.
Other suggestions for Luke? Leave them in the comments section. Barber Pole Photo Credit: Ross Griff
Nice post. I just want to throw in there that a diver watch with steel band can be pulled off pretty well in this look (not-too-formal shirts, rolled up sleeves, knit ties, khakis). It’s a step up from Timex Weekenders and can be a nice foil to a simple watch like one listed above.
I’m really digging the Orient Mako that I recently bought.
Links to any cheap knit ties like that one?
I love #5! My coworkers tease me for getting a haircut every 3 weeks. I had a boss who said, “You never want to look like you got a haircut; you want it to look pristine all the time.” SO I converted from every 5 weeks to every 3. And now no one says, “Hey Paul, you got a haircut!”
Also, Bulova is a great watch at a great price. It’s a classic American brand (even though no longer made in USA) that is super affordable. And there’s always some kind of sale/coupon at Macy’s if you’d prefer to see and try before purchase.
thetiebar.com has some great, inexpensive ties
Where can I find that purple tie?
Does that tie/plaid shirt (Ben Wyatt) look work for a guy in his late 40’s? I’m 49, and can dress business-casual at my law firm, and while I’d like to graduate from the white shirt/chino pants routine, I don’t want to look like I’m trying to recapture my 20s.
Used to be at LEC. I don’t see it there anymore.
I cut my own hair every 5-7 days. But mine just consists of a sideburn edge trimmer all around my head to create a very very close buzz. And no, I’m not bald, I just have always kept my hair very short.
I really need to start getting my hair cut more often.
I also dig the Bulova. It was between that and the Skagen 858XLSLC, and ended up going with the Skagen just because. Both are beautiful timepieces.
Great bag comments. I work at a university, and I bike around a lot, and while I want to carry a nice bag with handles, it’s too dangerous due to the weight imbalance of my handlebars. Might there be nice, handled bags out there that have inconspicuous strap attachments to allow for the best of both worlds, the messenger AND the briefcase?
I would recommend you ease your way into it and go as far as you are comfortable. Start with conservative checks, windowpanes, and tattersalls. Then try some shirts in larger, bolder tattersall or gingham. If you want to do full-on tartan-style plaids after that, go for it.
For good ideas on where to start, scroll through the Brooks Brothers dress shirt pages and look at everything that is not stripes or solids. I don’t think anything they show is age-limited. They also have some good tie-shirt pairing ideas, although they tend to be more formal than the Ben Wyatt look.
Yep. Sadly, that one is lonnnnng gone. Made in Italy. I think I paid $12.
I would replace the watch with upping your shoe game. Can wear the same dress pants with shoes from Target (eek) or with full grain leather shoes for a massive difference in effect. =)
That is the best of both worlds, and a shoulder strap is great for when you’re walking through airports. The Bosca does come with a detachable shoulder strap.
For something real inexpensive, KCNY has a few bags with top handles and shoulder straps. Some like to complain about the quality, but as long as you treat it decently, it’ll probably hold up.
You mean something like this? I got one in grey nylon/cotton, but I can’t fit all my files in it so I might end up returning or selling it.
If you have the money for it, Saddleback Leather Thin Briefcase. You can’t go wrong.
I just got the Saddleback Thin Medium briefcase as present from my parents for completing my Master’s program, and it’s phenomenal. Handle for the briefcase, shoulder strap for the messenger look, and converts to a backpack for easy transport while biking – a key component, as I just moved to a big city. My first day carrying it, I got a compliment on it from a woman who was interviewing me for a position at one of Boston’s biggest law firms. It’s definitely expensive, but totally worth it.
I am thinking about getting that Bulova, but I found a very similar watch on Amazon from Stuhrling Original for about the same price ($79), model number 601.33152. Does anyone have any thoughts on advantages of one over the other?
http://www.amazon.com/Stuhrling-Original-601-33152-Classic-Swiss/dp/B00132UP22
Really can’t go wrong with either at that price point. Personally I’d go with the Bulova. I think they make a better watch than Stuhrling. And the Stuhrling name has some negative connotations similar to Invicta.
Good post, Joe, it’s a great question (one that I face too), and the suggestions are right on. I would ADD upping one’s shoe game to wearing a watch. Going tieless but with a good jacket and good shoes (not those shineless chelseas I see everywhere), puts you way ahead.
Bulova is a no-nonsense brand – was American, now owned by Citizen last 2 years or so – with a great history (Bulova clocks are on the moon for NASA, timing for the Olympics, etc.). Not fancy, not prestigious (sold in dept stores) – just works.The other guy you mentioned sells novelty watches in the back of car magazines.
Once I bought my first pair of Allen Edmonds, I started paying attention to what shoes other men were wearing at work, or on the train. It really is shocking how many men are wearing absolutely horrific shoes to the office.
I really like this. Any thoughts on an alternative blazer? I’m moving to a big law firm in the Bay Area so dress is very casual and I feel that jeans, button up, AE strands and a jacket will be my uniform but I’m a little uncertain on the jacket, now that the BR seems to have disappeared.
> a watch says: “I have enough going on that I need to know what time
it is, but I’m also not married to my phone. You can’t get a hold of me
whenever you damn well please. Sometimes, people have to come find
me.”
Um, no…a watch says “look at my pretty watch”.
Or usually, “look at my expensive watch”.
Or, it says “I’m not creative enough to come up with more interesting ways to spend my money.”
Or, “I’m so uptight that I obsess on the time – it’s not enough that there are 5 different clocks I can see from where I am standing.”
Or, you know, “I’m hiking in the wilderness, I don’t have my phone and I want to know what time it is”
Or “I want to know how long I have left of happy hour, but I’m not rude enough to pull my phone out of my pocket while having a drink with friends”
Or “I’m on the subway, the train has no clock, and I want to know if the delayed train will make me late for work”
And I don’t own a watch that cost more than $100.
People who incessantly play with their phones look distracted, and I do not think it is a good idea to look distracted like that during an important interaction . I, for one am not always in a location, even at work, which has a clock (let alone six).
I do the same thing, but I’m definitely going bald 🙂
You are one angry bird.
Well, it’s hard to get a watch on when you have wings!
Unfortunately once you notice, you can’t ‘un notice.’
While I think it’s absurd that some men think of watch as an accessory and nothing else simply because they have a phone that also tells time, I think it comes down to manners. Whether you realize it or not, it’s rude to pull your phone out mid conversation just to check the time because the person you’re talking to has no idea what you’re looking at. They might get the idea that you’re checking to see if you’ve gotten a text or an email and that it’s more important than your conversation. Those of us who were raised with manners wouldn’t do something like that and thus like having the option of being able to discreetly glance at their wrist to see what time it is. That plus the fact that it’s always faster to look at your wrist than to reach into your pocket and pull your phone out.
I’m happy to let guys go the phone route though….it just makes us gents who wear them look that much better (and mature) by comparison.
True that.
Your “logic” could be applied to any piece of apparel in this post or on this site (“Look at my structured blazer!” “Look at my shiny shoes!”). But if you approve of dressing nicely (which you must since you are reading), why can a nice watch not be included in the ensemble? It is arguably more functional than a belt (when pants fit properly).
While I personally would be very happy to own that Bulova; in the realm of nice watches, it resides on the low end. Help me understand your malcontent regarding this $75 timepiece.
And pray, do tell, what would be an “interesting way to spend my money?” I am always dreadfully concerned about what others think of my spending habits. Surely others can relate…
Personally, im not a fan of the “Adam Scott” look. Maybe its just me but it looks like a hipster intern. I can’t take someone serious in a knit tie, and gingham. Its like “hey look im trying to dress in my big boy clothes but I could also be mistaken for a uo sales person”. Suck it up and put on some well fitting slacks, leather cap toe oxfords, maybe narrow tie and dress shirt (white, light blue or nice stripe). Inception wardrobe > Deathcab wardrobe.
Personally, im not a fan of the “Adam Scott” look. Maybe its just me but it looks like a hipster intern. I can’t take someone serious in a knit tie, and gingham. Its like “hey look im trying to dress in my big boy clothes but I could also be mistaken for a uo sales person”. Suck it up and put on some well fitting slacks, leather cap toe oxfords, maybe narrow tie and dress shirt (white, light blue or nice stripe). Inception wardrobe > Deathcab wardrobe.
You know, it’s really just about as rude to look at your watch in the middle of a conversation, too.
Damn…this is one butthurt comment. Because the dude is wearing plaid rather than solids, you think he’s a little kid? Most of his ties are just narrow-ish silk stripe ties. His slacks, and his shirts as well, actually, are both very well-fitting.
Also, I think you are getting the actor Adam Scott confused with the character Ben Wyatt.
Really the only hipster thing he wears is the narrow ties, but you recommended that in your comment too. Not everyone has to conform to the ultra-conservative, formal look you seem to prefer. Having a little fun with your style is often a good thing.
Agree. Ben Wyatt looks does not look very serious and kind of little kidish to me. I would upgrade to grey wool pants, nice shoes, and blue, white, or subdued patterned dress shirts and no tie. It won’t be shock to your co workers since you really will not be adding any item to your look (like a tie) but will also be wearing some of the same components as your superiors (dress shirt, wool pants, dress shoes).
You can work your way up to a jacket.
You’re absolutely right and it’s something that you should avoid doing at all costs. I wasn’t making the case for obviously holding your wrist up…the key phrase to what I said was ‘discreetly glancing at your wrist.’ Subtlety isn’t really an option when you’re using a phone to tell time.
I would go with the Bulova or the Skagen linked to above. I have the Stuhrling and the Skagen, and the Stuhrling just feels kind of cheap next to the Skagen. It’s hard to tell in the Amazon pictures, but the band on the Stuhrling is very shiny/glossy and a bit stiff. The face on the Stuhrling is bleach white while the face on the Bulova and Skagen are silver, which I think give them a more modern look.
Not butthurt at all. Just my opinion that his clothes look a little too hipster. Not sure what the precise definition of “narrow” is (I think I remember reading that 2.75 to 3 inch is narrow) but his ties seem more closer to skinny ties. And yes his clothes are well-fitting, but in my opinion they’re far too casual (chinos 24/7, plaid shirts, etc). Especially the fact that this article is about “promoting” your office style. The guy mentioned he’s in Dockers and dress shirts now. So the “Ben Wyatt” look is really only adding a psuedo tie. If you’re in business casual and the higher ups are in full blown suits go a little closer to their look minus the jacket. And if its an issue of $, H&M has decent looking slacks for $30.
And yes, I was referring to Adam Scott’s character. Didn’t know his name.
If a dude dressed like Ben Wyatt came into one of my meetings my first question would be to ask him when Purity Ring’s new album comes out. Kidding. But sort of not.
:]
Another plus for wearing a decent watch is that it gives pretty ladies an opportunity to ask you for the time. It can be a great icebreaker. Not as good as a puppy, of course, but easier to haul around.
Okay guys. Let’s move on.
Like I mentioned above, I think his ties would be considered ‘skinny’ not ‘narrow’. And I mentioned narrow ties because they look slightly less conservative, and if you’re on the slimmer side, most people don’t even notice and they’ll look nice. And if a proper dress shirt and leather oxfords is your idea of “ultra conservative/formal”, well, that’s just sort of weird. You can certainly have fun with your style without looking too hipster/ben wyatt.
I’m telling you, if this guys higher ups are all in suits, and he walks by them in the hallway in a knit tie and plaid shirt, theres a good chance they’re going to make fun of him behind his back. I see it happen often at work.
I like that clean watch, as for blazers, what about that Target Kensington? Much easier on the wallet
Any reason you went with black instead of brown band? http://www.amazon.com/Skagen-858XLSLD-Steel-Super-Brown/dp/B004N98S3A
One of the most commonly recurring themes on this site in the comments section is confusion about what constitutes ‘hipster’ attire. I know it’s subjective, but to call Ben Wyatt’s outfit hipster is a real stretch…
Great Thread Joe.
Really feeling that watch. Does it come in brown?
Office style definitely depends on what part of the country you’re working in. I work in one of the most conservative professions and even the partners come to the office in jeans and a sport coat on most days.
Not sure if they are the “Kensington” but I have seen Merona cotton blazers (Navy & Khaki) at Target that are great-looking & summer-ready. Unfortunately for me, the Medium shoulders are a little too large & the Small is perfect except that I threaten to turn into the Hulk when I cross my arms. Perhaps the Med. could be tailored & turn out ok.
I have that Sateen Blazer and … it … is … amazing.
I read somewhere (maybe an Amazon review) that the band on the Bulova is a bit thin/cheap. Can anyone comment on that?
Hey Joe, any idea where I could find a shirt similar to this? Totally dig the Ben Wyatt look. 🙂
http://benwyattfacialexpressions.tumblr.com/post/3566114217/being-his-charming-self
Sounds like you’ll want more than one well-fitting, unstructured blazer. In which case, I recommend at least one in linen, possibly khaki. Of course you’ll also want a cotton one in blue for your dress up days. Maybe seersucker for casual Friday?!? Regardless, if you aren’t ready to order yours made-to-measure, you’ll need to hit the stores. The usual suspects are: J Crew, Banana Republic, and perhaps Macys.
I agree – he looks like a little boy, certainly not a business exec or successful person to work with.
Funny coming from a site where guys spend major $$ on shoes and other accessories.
A fine watch is like any other fine item – a great car, a decent piece of furniture, awesome shoes or a well-made suit – the difference is immediately apparent and once you experience quality you won’t go back.
Price is not the only measure – sometimes a Timex casual watch is appropriate, sometimes a Swiss automatic.
If you want a Rolex quality watch but not pay Rolex prices then a British Company called Christopher Ward is the way to go. Swiss made and quality components and styling. I recently got the Christopher Ward C11 and it’s awesome, so many people at work admire it and pay lots of compliments. I already looking at the C60 trident and C5 as a next present. Just thought I share this info for anyone wanting to spol themselves without breaking the bank for an Omega or TAG.