Work Style

    Outfit of the Day: A Smart Look for a Casual Office

    25th September 2012

    Today’s Outfit of the Day is inspired by Mark, a reader who just wants to look nice at work. Us ladies should be so lucky to work with more Marks in our offices.

    Mark asks:

    My office is pretty casual, for financial services anyway. One of the many benefits of being in Southern California.  Currently I wear a pair of nice slacks, dress shirt and loafers most days though I throw in some jeans sometimes if I know I won’t have any meetings on a particular day.


    I was looking to add some chinos to the mix as something in between the slacks and jeans.  Something comfortable but also decent looking.  I know pleats are bad but can you give me some guidance on cuffs?  Also, while I’m asking, can you recommend some casual, but nice shoes?  I’m currently either a loafer or chuck taylor sort of guy.  I’m a little lacking in the in between.


    As an example and because their shorts fit me well I was looking at these [from Land's End]. Thanks for the help.



    I used the pants in question, and chose khaki because it’s so versatile. They’re still a little..mmm, stodgy? But knowing a brand fits is invaluable, so I won’t override them here.

    Don’t be afraid to play up contrasting patterns in your shirt and tie, like with this striped Brooks Brothers dress shirt and polka dotted Paul Smith tie. It adds personality but still looks professional.

    Us ladies notice a guy who punches up a work outfit with some visual interest. It shows extra effort. We like effort.

    I was really stuck between the two pairs of shoes, because they’re both great options that will instantly elevate your footwear game. Then I found this reversible belt, and…problem solved! The other little bits – the watch, the bag – add to that “finished” look that I think so many guys are missing these days, where everything’s, y’know, fine, but it’s not really a look. It’s just a bunch of clothes.


    The Details:

    Pants: Land’s End, $44
    Belt: BOSS, $95
    Brown Buck Shoe: Original Penguin, $100
    Black Saddle Oxfords: Florsheim By Duckie Brown, $335
    Shirt: Brooks Brothers, $88
    Tie: Paul Smith, $135
    Bag: Jack Spade, $425
    Watch: Fossil, $135


    • Derek

      Those pants. And those shoes. And that shirt. And that tie.

      What am i looking at.

    • average joe

      Dear Megan – Even though I hate the Packers, you were robbed last night. That is all. JK.

      • Style Girlfriend

        oh man! I heard about that! what is going on with the nfl??

        • average joe

          arguing over money

    • average joe

      There are a lot of good pieces shown here MG, but not all of them would work together. Let’s start with the good stuff though…

      Those brown shoes are a hit. The detailing on them makes them more casual and they’d pair well with khakis, chinos, or jeans. (They wouldn’t work as well with dress pants though). The shirt would set up nice against khakis and those shoes you’ve selected too.

      I’d avoid black shoes with khakis though. I know it can work – but unless you really go all out flamboyant peacock-ish, you start to look like every other guy in the office with rubber soled square toed Sketchers. (And most guys aren’t going the peacock street style route). This oufit, tie included, would work beautifully with the brown shoes. Switch in the black shoes and it comes off a little schlumpy.

      Since you asked (about cuffs), I’ll expand it to the whole piece. Those khakis are a little “old man” if you ask me. Several of Land’s End’s cuts cater to the older generation – fuller cuts, less slim. For my money, I’d go with Nordstrom’s brand khaki’s – about $70 plus free tailoring. There’s other brands that are even slimmer that Nordstrom’s but you’ll run close to $200 – but if you pick them up at Nordstrom’s you’ll get that free tailoring as opposed to J Crew or some place like that. Personally, I’d avoid tailored cuffs on khakis or chinos. If they’re tan dress pants, then tailored cuffs would be ok.

      • Mark

        I hear you on the Land’s End pants. They’re fairly unremarkable and safe. I’m open to other options.

        There’s a Nordstrom across the street. I may go over there and check these out:

        or these:

        Thanks for the tip on the cuffs and thanks Megan for the help. I love the shoes and Brooks Brothers is definitely a staple in my wardrobe.

        • Style Girlfriend

          Of course! Will be anxiously awaiting a pic of your new look :)

        • K to the Poon

          I’m a huge fan of Bonobos pants. I find that the fit for them is similar to Levi’s 514′s, which is perfect if you don’t have skinny legs, but are still looking for a slimmer fitting pair of pants. Definitely a better option imo than the LEC ones above.

          • Mark

            Good to hear. I’ll have to check them out. Super skinny doesn’t look good on me, I don’t think.

            • Style Girlfriend

              I think most guys would be surprised to find out how good they look in a slimmer cut pant – give them a try at least.

            • K to the Poon

              That’s exactly what I thought at first, but I found that it makes a huge difference in your looks. I grew up wearing baggy jeans, because that’s just what kids did in the 90′s, but the slimmer fits make a great impression. Makes an outfit go from a-ok to awesome.

          • Style Girlfriend

            Love Bonobos!

    • Freaketchic

      A good piece of advice, although I’d check for a better fiting pair of pants. Also, a tie without a coat, or cardigan or at the very least a tie bar to balance it? If you are going to wear a tie you can’t let it just float around. You need to balance it. The simplest method to look “finished”, as Megan rightly suggests, is to get a vintage tie bar on ebay or etsy (for cheap).

      • Style Girlfriend

        Face palm on the lack of a tie bar – thank you!!

    • Kalen

      I work in a super casual workplace. I am talking jeans, maybe a polo, and steel toed shoes for the office folk. I get right after it, sport coat, tie, no short sleeves and Allen Edmonds shoes. Did I look like a jerk at first? Sure. Now it is my style though, and it only took a week or two for people to ask why I am so dressed up. I received great advice when I was just getting out of college….”don’t make it a crime to look good!”

      If I had the money, I’d suit up every day. Just because everyone else looks like a slob doesn’t mean you have to drop to their level to “fit in”.

      • Mark

        I live by the “dress slightly better than your clients” which is not hard to do here in SoCal when clients come into the office in Hawaiian shirts and flip flops (we’re near the beach so I think they’re still acceptable). I just try and keep it neat and put together but still comfortable.

    • CJL

      Say no to old man pants and black shoes/belt/watch with khakis. And cuffs.

      • average joe

        hear hear

    • Jim

      Navy or light grey cotton chinos are nice alternatives to khaki if you want to mix it up a little. I’m not really a fan of the black shoes Megan posted, but Florsheim makes some great shoes for under $200 in their Limited collection. I think the most versatile shoe you can own is a dark brown blucher wingtip like these:

      Dressing well doesn’t necessarily mean dressing up. Wearing a suit when everyone else is in jeans is just silly, and even a tie by itself might be too much. Make sure you find the best fits for your shirts and pants (that Brooks Bros’ button-down is labeled “Slim fit” but it’s not, at all — unless you’re overweight you need to go with BB’s Extra Slim). If you’re not wearing a tie, make sure your collar buttons down. Maybe mix in some light cardigans or V-neck sweaters, or even an unstructured cotton sportcoat, if the weather calls for it.

      Absolutely, a sharp watch and bag will upgrade any outfit. But I wouldn’t worry so much about putting together a “look” for work. Sure, effort counts, but buying ridiculous two-toned patent-leather/suede shoes because you saw them on a blog isn’t real effort — you need to take the time to find the right fits and colors that flatter you and work together (for example, don’t wear khaki pants with black shoes.)

      Also, you’re a grown-ass man: just buy two belts.

      • Mark


        I usually go with khaki, blue, olive, grey and , maybe black for pants. I’m just due for an upgrade which is why I was looking.

        Those shoes are nice. I need some more versatile/casual shoes.

        I’ve never gone with a fitted shirt but I may try it out. The regular brooks brothers ones are definitely a pretty generous cut.

      • hornsup84

        Not sure who you’re trying to impress with your tone, but BB Slim fits are a perfectly fine fit for those of us who weigh more than Megan and who work in conservative industries and/or prefer some room to breathe in our shirts. One may need to tailor the waist a slight bit so that the shirt doesn’t start tapering back out if you’re tall, but for OTR shirts that are consistently sized, they aren’t a bad option.

    • ChrisReetz
      • Style Girlfriend

        I like it!

    • Guest

      A Style Girlfriend outfit without chukkas? I feel lost and confused.

    • ct

      Too american. Who wears stuff like this to work? Poor guys.

      • Style Girlfriend

        curious: too american how? too casual?

    • grzars

      Tie no coat? Makes me nervous. I’d rather lose the tie and throw a soft shouldered blazer over top.

    • corrid

      I dislike almost everything here, sorry, but major bonus points for paul smith! so i guess it evens out. The belts are nice too…