Engineering The Perfect Business Wardrobe feat. Ian Anderson

April 3rd, 2014

A well-dressed man’s wardrobe doesn’t have to be large. You certainly don’t need all of this.

The beauty of menswear is that you can be sharply dressed for just about any occasion by investing in, I’d say, roughly 50 quality pieces (maybe I’ll do a follow-up post on that).

Nobody understands the science of building a streamlined, versatile wardrobe better than Ian Anderson in San Francisco. Ian is a structural engineer who took a scientific approach to redesigning his wardrobe when he graduated from Stanford and entered the working world.

“My interest in men’s clothing began when I was starting grad school. I was working on my Master’s degree at Stanford and suddenly realized that I would need a major wardrobe overhaul when I entered the workforce after graduation. I spent a good amount of time learning about clothes and slowly creating a professional wardrobe in order to prepare for life after college. My college-kid thriftiness made me concentrate on buying only the most versatile items that I could find. It also made me focus on quality and getting as much as I could out of every dollar I spent. Now that I’m out of college I have a bit more flexibility in what I can purchase, but I still find myself drawn to the most basic and pared-down items.

My time working in downtown San Francisco taught me that looking sharp helps, but standing out too much does not. At the end of the day, I try to dress in a way that leaves a good impression but doesn’t stand out; I want the people I interact with to remember me for what I say, not what I wear. And to accomplish this, I find that the more limited my choices are, the easier it is for me to leave the house looking my best.”

Here Ian shows us some of the staples of his day-to-day style, and shares some of his science beyond building an efficient business wardrobe.

    1. Two Suit Tango


    “This is a great example of how I like to dress for a typical workday – simple, neutral-colored tailoring in classic-leaning proportions. I try to avoid overly trendy details like cropped and tapered fits or skinny ties/lapels in my professional clothing. I want to feel like a professional when I’m at work, and I use these clothes to emanate that feeling. Confidence is everything in corporate America, and these items are my secret weapon.”


    “One of the easiest ways for me to increase the breadth of my professional wardrobe is to wear my suits as separates (of course, this must be done with some restraint so that the suit pieces don’t wear at different rates).

    I wouldn’t normally wear worsted wool suits as separates like I’ve done here, due to the fabric’s obvious “suit-y” feel. To compensate for this, I’ve added some texture with the raw silk tie and suede captoes. This gives the look enough contrast to feel cohesive, in my opinion.”


    “A few months ago my buddy Conrad in NYC sent me this tie from his new neckwear collection Conrad Wu. I absolutely love it, and think that his ties might be the best out there for under $100. They’re made out of incredible fabrics from Europe by a small group of artisans in New York City.”


    2. Study Your Ratios


    “You might be noticing some similarities between this and the first look; that’s no accident. I almost exclusively wear grey trousers and blue shirts in the office, and cycle through neutral colors like brown and navy for my ties and sportcoats.

    Having this go-to “uniform” not only makes getting dressed easy, but it allows me to focus on the important things, like getting the fit right, instead of trying to figure out what ties goes with what shirt. As long as I stick with a light shirt, dark tie, and simple jacket, I know it’s going to be bulletproof. Some may find all of this boring and restrictive, but I find great satisfaction in the simplicity of it.

    Inspired by Articles of Style and other men’s style websites, I started writing about menswear on my blog From Squalor to Baller. Contrary to what the title might imply, it’s a place where I discuss my thoughts on dressing simply and classically for various settings and my search for products that provide the best quality-per-dollar ratio.”


    “Another aspect of my wardrobe that I tend to fixate on is the fit of the collar and lapel zone. I think this is the most critical area of tailored clothing, and it is often overlooked by men. I try and keep my collars substantial enough to tuck neatly under my jackets, and keep my ties and lapels in proportion with the shirt collar. When these three elements are in harmony the whole rig looks so much better.

    My late grandfather is my style hero, and this vintage Omega is one of several items that I have inherited from his closet. I swap the band from time to time, but it’s on my wrist every day.”



    • Blue stripe shirt by Proper Cloth
    • Navy Silk knit tie by Ralph Lauren Purple Label
    • Pocket square by the Tie Bar
    • Watch by vintage Omega
    • Grey Flannel trousers by Howard Yount
    • Oxblood Wingtips by Allen Edmonds

    3. California Tuxedo


    “Here’s an outfit that can get you through every Bay Area event on your social calendar – for years to come.

    Lightweight navy blazer, chambray shirt, worn-in chinos, and slip-on loafers. The California Tuxedo.”


    “I rely on Proper Cloth almost exclusively for my dress shirts. The online made-to-measure scene is a bit murky at times, but this NYC-based company has provided me with great shirts over the years. Now that I have my size perfected, it’s a little too easy to order a new shirt.”



    • Navy Cotton blazer by Boglioli
    • Blue Chambray popover by Proper Cloth
    • Khaki Chinos by Bonobos
    • Brown Belt by Equus Leather
    • Pocket square by Kent Wang
    • Watch by vintage Omega
    • Brown Penny loafers by Crockett & Jones for Brooks Brothers


    Thanks, as always, for reading.

    Yours in style,

    Articles of Style


    Photography by Alex Crawford 

    • Big Jon

      This was awesome. Add in some cool fedoras or Kangols and then it works for me.

    • TheDoctor

      As a certified member of the type of straight female persuasion that enjoys looking at dudes, I can 100% vouch for the awesomeness and virility that is Ian Anderson’s sense of style.

    • JM

      It’s funny how a 7.5 or 8 inch leg is considered to be large by some. It shows how large the adoption of skinny jeans truly is. Loved seeing Ian get the recognition he deserves.

    • Owen

      First of all I have to say that Ian, you look great! Your colour and material choices are well considered and the fit of your jackets is perfect.

      I’m not really a fan of the wide openings in the first two looks. In my opinion I think tapered trousers would provide a younger, more dynamic appearance to these two looks,.

      I’d happily wear look #3. That Boglioli jacket is beautiful and is certainly a true staple garment!

    • Gazman

      Have been reading Alex’s insightful blog for some time and agree with his style philosophy. I’m pretty sure it was him but go check out his post on form and function as it relates to style – spot on. The less-is-more approach is the epitome of style.

    • RAS

      Best post yet! CBD done right.

      • From Squalor to Baller

        Thanks! I’m all about CBD and old man style – that’s where it’s at!

    • Matto

      Long time S2B reader here. I’m a big fan of Ian’s style, and particularly the reasoning behind it. 1 & 3 are by far my favourites. What I love about #3 is that it looks great in the real world – it’s not super-sharp, it looks easy to wear without being ostentatious, whilst still maintaining on-point details.

      Great article.


    • David

      The shirt in look 3 is killer! I only recently bought my first chambray shirt and I’ve become a real fan of the fabric.

    • Jaws

      What’s your experience/review of Proper Suit in comparison to your other MTM/OTR?

      • From Squalor to Baller

        That’s a good question with a long answer, but I’ll try to answer it succinctly. The jacket above from ProperSuit was half of a suit that was given to me by the owner of the company. Many aspects of it fit well, but the jacket length and button stance are both about 1″+ higher than what I desired (which is a lot). A big difference between Proper Suit and, say, Beckett & Robb is that PS doesn’t offer any real MTM “security” – tailoring $, remake options, etc (at least not to my knowledge). That’s their business model, and I have no problems with that, but it essentially means that what you get is what you get and you’re on your own from there. I wasn’t too upset since the item didn’t cost me anything, but if I had paid $700 I would have been. The main reason I’m wearing it in the photos is because when I got dressed that morning I had no idea I’d be in front of the TSB lens.

        At the end of the day, I’m starting to have a strong preference for off-the-rack clothes (although it certainly wouldn’t seem that way, given the photos above). I’d rather have something 90% of the way there than something that is unknown and could be perfect or unwearable. There is a place for MTM clothes, but there’s something to be said for knowing exactly what you’re getting. Hope that helps.

    • AFH

      Look 2 just isn’t that strong – the sports coat is kinda dull, the office shirt feels off; a really great choice of square could have saved the outfit but…. it was not to be.

      I think he does a good job of making double worsted work in Look 1, but he does it using a special tie. The half-placket shirt, which is less versatile than the full placket version, makes Look 3. Versatile pieces in brown, grey and blue are great, but they only take you so far and I think this is demonstrated here.

      • From Squalor to Baller

        Look 2 is actually my favorite by quite a bit, and features many of my favorite items to wear. Two muted patterns, lots of texture, and rich, simple colors. And I think the fit of Look 2 is also the best by far, but that’s just me. A heavily patterned pocket square would have added some more complexity, but I decided to abstain. Thanks for the input, though! I totally agree that there’s more than one way to make these looks come out well, and many would prefer to take them one notch up in complexity. Feel free to expand on what you’re saying about the the sportcoat and shirt being off.

        • AFH

          A plain white pocket square would have been better imo than the one you chose.

          I can and will break it down, but the photo on my laptop screen – I just see a look that doesn’t quite gel and the analysis comes afterwards.

          The shirt just looks too much like an office shirt imo; an Oxford, or at least a plain blue, would have been a better choice.

          I think the flannels are a touch too pale for the jacket – that might be my personal taste; I do appreciate the lighter flannel for the Spring.

          In the final analysis, I think the jacket is the problem. You’re wearing a November jacket with March basics, though I’m not sure the shade of brown works optimally with your skin tone (similar to mine incidentally) – again on this photo on my laptop.

          Don’t get me wrong, you are doing a good job of getting 80% of the results from 20% of the effort (or whatever) and there’s nothing wrong with a bit of self-satisfaction. I do think the idea that you can build a great wardrobe with 50 pieces is suspect, unless you play it very, very safe.

          • TO

            Thinking over it little too much my man- Ian looks great in look #2 and it perfectly expresses his preference of fit.
            And how many pieces do you think you need- 100? 200?

            • AFH

              a) If you’re going to patronise me, please at least read the post;

              “I can and will break it down, but the photo on my laptop screen – I just see a look that doesn’t quite gel and the analysis comes afterwards.”


              b) 1004

              • TO

                I don’t understand what that quote means. I find it unclear what you’re saying there. To me, it sounds more like you are patronizing Ian.

                But at the end of the day everything you say is your opinion and I can’t take that from you, I just wanted to point out that I think the guy looks great.

                • AFH

                  Well if you don’t know what that quotes means, then I don’t really see how you can accuse me of patronising him. I think the meaning is pretty clear; I made a snapshot judgement and then I worked out why I came to that judgement – partly at the invitation of Ian.

                  You can point out that he looks great, indeed you have. You don’t need to attack me to do that.

                  • AFI

                    AFH is a clown

                    • Got dat Heat 4 niggas – AHVB

                      After reading the above exchange, I’d have to agree. WTF is AFH talking about?

                      • AFH

                        If you provide specifics, I can clarify…..:-)

    • Fernando

      One of my favourite posts ever. A perfect example of how someone can look great without overdoing anything. It doesn’t look like he is trying too hard. It doesn’t look like he is trying to be noticed. No frills. Just simple and stylish. Great job. I’ll definitely check out his blog.

      • Gazman

        I agree with your comment. Ian keeps it understated and classical. Too many style blokes over-do everything and dress each day (or for their photo-shoot) like they’ve spent an hour beforehand scrolling through #menswear tumblrs, ticking off every ‘trendy’ item. Yes, check out his blog. It’s informative and interesting.

    • Al Bizzy

      @fromsqualortoballer:disqus Good job, Ian! Way to rep us out here in the Bay.

      • From Squalor to Baller

        Thanks dude! I learned from the best. It was a fun shoot, that’s for sure!

    • MF

      No worries – I think its awesome that you rarely re-blog and actually put up helpful posts geared towards guys like me in their 20’s. Also, since I live in Palo Alto and go to school in SF, I feel obligated to rep Bay Area menswear folks!

    • TO

      Well done, Ian. It is so obvious that your proportions on each look are so well thought out.

      Some underlying tips I got from this was to find go-to custom online vendors and be on the look-out for (less expensive?) design collabs to streamline a budgeted business wardrobe.

      You pull off “bigger” proportions very well, such as a wide leg opening and fuller trousers. But you are also probably 6’4″ right? Which def helps with this. Look #3 is so well balanced, every item is perfectly in sync with all the others… where are those socks from?? The ribbing on them is insane.

      • From Squalor to Baller

        Haha I’m a hair under 5’10” with a 36″ chest – tricked ya! That’s the power of good proportions, and one of the reasons I don’t opt for super slim clothing. I think the socks are from Uniqlo, nothing too fancy.

        • TO

          Wow! That’s incredible! I thought for sure you were a big tall guy. What is your preferred leg opening (or the ones in this post) if you don’t mind me asking? Well done.
          Dam, I was at Uniqlo’s flagship last week, I should have checked out their socks! I love lux the look of the ribbing on that pair.

          • From Squalor to Baller

            For dress trousers like the ones above, I usually opt for 7.75-8″ openings (which isn’t that big, really, they’re just not super tapered). For casual stuff like jeans I will go slimmer, but I never go under 7.5″.

            Yeah, I’m all about Uniqlo socks right now. Hard to beat for the price.

    • Chris

      Is that the Soft Ivy collar style from Proper Cloth on the popover?

      • From Squalor to Baller

        Yes it is. It’s great, but looks/feels best on thicker fabrics like oxford cloth and chambray IMO. Great proportions.

    • Jeanscuffed

      Although I do like a bit of flair or edginess in my wardrobe and seeing others display that as well, I tend to find Ian’s looks pretty well put together. Look #3 is my favorite for the casual vibe. I’m not really feeling the looser drape of the trousers he has in Looks #1 and #2 but like Dan said before, looser duds might be coming back, to say that Ian might be one of the “Cool Kids” Dan was referring to. Good stuff guys.

    • Andrew G.

      This is one of my favorite TSB posts. Well done Ian; you’ve got some serious style. I love FSTB!

      • From Squalor to Baller

        Thanks Andrew! It was a lot of fun working with the TSB guys on this. Glad you’re a fan of the blog!

    • John B

      I’ve recently discovered his blog and I really like his style. Looks like there’s a light blue windowpane check on the trousers on the first look which is pretty subtle but awesome.

      • From Squalor to Baller

        Good eye, John – there definitely is a subtle check! Thanks for reading.

    • Alex

      Dan, please do a follow-up article on the 50 essential pieces. I think that would be extremely useful to a lot of us here.

    • Geezer

      I love this post. It is realistic. You could wear this style in many situations without looking like a peacock. Well done.

    • kid_icarus

      This exceptionally cold, harsh, and long Winter, here in the Northeast US, has put me into a sort of style funk. It’s been jeans and t-shirts and chunky shawl-neck cardigans for months on end. I told myself I would start getting more varied and creative in my outfit choices once the air started warming up, but now that it is getting (slightly) warmer, I’ve been having a hard time actually doing so.
      This post seems to have helped me realize one of the reasons why – having far too much in my wardrobe. I’m admittedly a low-level pack rat, so I hold onto clothes long after the point where I’ll no longer keep them in regular rotation. Having so much to choose from does seem to make picking an outfit more difficult. I think I need to pare it down.
      So, thanks for this post, TSB and Ian!

    • TT

      Def a hilarious left brain/right brain thing going on here. But his approach is, uh, straightforward, if not particularly creative.

    • Shawn

      Ian, I am a follower of your blog FSTB and I’m glad you made an appearance here! My favorite look of yours in the second; that Suit Supply jacket fits you perfectly and those HY trousers are “on point”. I also like the fact that your belt hardware matches your Omega case in color! If I may, can you tell me which Proper Cloth collar is this, in look # 2? I’m about to order my first shirt from them and I can’t seem to decide between 2 or 3 of their collars!


      • From Squalor to Baller

        Hey Shawn – nice bumping into you over here! It was a lot of fun putting this together with the TSB team. That collar is the “President Spread” – 3″ points, 5.5″ spread, super easy to wear. I’m using the normal fused one here, but they just released an unfused version of it if that’s your thing.

        • Shawn

          Thanks man for the reply! Best regards!

    • Miguel

      A great feature, as he says, he tries to keep it simple but looking good at the same time by investing in pieces that go a long way,

      Thanks guys.

    • Sergio Arteaga

      By far one of the best features on the site, ever! Ian, thank you for showing simplicity is key and for showing me that I should really invest in some light gray trousers or suit.

      • From Squalor to Baller

        Thanks so much, Sergio! Glad you enjoyed it. Yeah, I’m all about the gray trousers (obviously).

    • Adrian B

      Nailed all three but number one is definitely my favorite. I go to TaT for nearly all of my suiting so it’s great one of Jason’s pieces on here. As for the Wu tie…..dat slub
      Bravo Ian !

      • From Squalor to Baller

        Dat slub indeed. Thanks, Adrian!

    • MF

      I don’t know if there was a link to Ian’s blog in this editorial, but all TSB readers should check out his blog “From Squallor to Baller” – I think it is easily one of the best menswear blogs out there due to its original and helpful content.

      • From Squalor to Baller

        Thanks so much for the kind words! There’s a lot of great stuff out there, and I’m honored that you think it’s worth mentioning. It’s been a lot of fun to write.

    • Mr Saint

      Really helpful ‘real life’ post – thanks Dan, Alex and not least Ian.

      Some useful pointers about constructing a wardrobe on a budget that will last you years to come. I just wish I had Ian’s foresight (and this website) as I was entering my first professional job after graduation. Years of expensive ‘fashion’ choices mixed with chronic under investment in correctly fitting, quality basics like jeans, shirts and shoes cost me hundreds (thousands?!) of pounds and I still found it hard to put an outfit together.

      My style journey could be summed up in three words that can be appliaed to nearly everything in life…. education, education, education…

      Keep up the good work y’all.