Reader Question: Classic Style at the Workplace with Business Casual Dress Code

Words by: Andrew Williams

I am graduating college in 6 months, have had a few unpaid internships, and all of a sudden find myself with the chance at an incredible job.  I have read a few of your articles on suits on a budget, I especially liked the one on maximum shirt and tie combo (, but I had a couple of questions.

1. How much does classic style differ from region to region?  I’m hoping to work in Silicon Valley and from my experience, the atmosphere is much more relaxed.  Ties are uncommon, jeans with a buttondown shirt is very common.  Keeping in mind a recent graduate’s budget, how can I straddle the line and look laid back but not sloppy, and not overdressed/classic?

2. Operating in this internship and the interview process, I have found myself in a variety of situations.  I have been invited to dinner, afternoon family tea, breakfast/lunch, as well as a semi-touristic visit to the city.  I always visit the site to understand what is best to wear, but how do I make the transition from a sloppy, sports memorabilia-wearing college student, to a Silicon Valley professional on a budget?


Dear Graduate,

First let me thank you for your e-mail and congratulate you on your exciting new position. I thought I’d answer this question in two parts. Part 1 will cover a few general principles which should help you. In the second part we will cover the ‘core wardrobe’ concept and I’ll list those key items I’d buy if I were in your position.

1. Find a look that works for you, and if you can a role model or two

The essence of your question, as I see it, is how can I dress well when the environment I work in has a relaxed view of business dress? This is a problem that many men face, particularly if they work in the creative industries, though not an insurmountable one. Sadly, from what I observe on the Tube each day most men make a complete hash of it. They don’t look well dressed and casual, merely scruffy.

I’ve always defined classics as items of clothing and looks that flatter the wearer and all those who subsequently adopt them. This is why they stand the test of time and translate the world over. While regional variation is a factor, it’s not so big a factor as you might think. While an English suit is different from an Italian suit they are still fundamentally the same thing. The devil lies in the detail of construction and silhouette.

I guess my first bit of advice is don’t get hung up on any one idea of classic dressing. If I asked you to list some classic dressers I’d bet that it would be dominated by men whose principle mode of dress is formal, suited and booted. But in my view Steve McQueen is one of the great all time classic casual dressers, managing to look good, comfortable and at ease all at once. Except in a few film roles, like the iconic Thomas Crown Affair, the man almost never wore a suit. His ubiquitous Baracuta G9 ( Harrington jacket) is in some circles, including my own, considered a classic. But there is nothing formal or flash about a Harrington. The same can be said of button down shirts, chinos and even jeans; but they are classics and can be made to work to wonders. This brings me neatly to my next point.

2. Remember the three F’s: Fit, Fit and Fit

What really sets apart one man from another in terms of dress is the fit of the clothes he wears. If your clothes fit properly they will flatter you and you will always look smarter that the man who ignores this; that applies whether you’re in the same type of clothing as the man next to you or you’re in jeans and a shirt and he’s in a suit. Poorly fitting clothes no matter their cost or type never look good. This lesson is true whether you’re skin and bone or a hefty unit. An example of this in my case is jeans. I freely admit I buy Gap jeans. I’ve tried designer label pairs but they are usually too short in the drop and too tight around the seat and crotch. That’s not to say Gap’s are always perfect in every other regard. But I can get that fixed and do so. I’ll have them shortened and hemmed and will even get the legs tailored either from the knee down or mid thigh depending on how sharp I want them to look. Whatever you buy take the time and make the effort to get it altered by a good alterations tailor. In my case this always pays a dividend over and above anything I might achieve by spending more money on the jeans in the first place. As it happens the cost including alterations works out cheaper.

The only exception to this rule is when it comes to jacket shoulders. Few things look as cheap as an overly large jacket shoulder. They are a nightmare to fix so you’d be better advised to simply return the garment to the rack. If necessary find a different label to buy your jackets from.

3. Don’t be too proud

Money is no bar to dressing well. Indeed, as the point above also highlights, it can sometimes be a hindrance if it inclines you to believe that simply by spending money on clothes the job is done.

Find clothes that fit and require the minimum of corrective surgery no matter what the retailer. There is a lot of snobbery concerning clothing and it’s easy to get caught up in it. Find retailers that work for you and stick to them regardless of the conventional wisdom. And that can include vintage and second hand outlets. It doesn’t matter how you acquire what you need to acquire, only that you acquire it. While these days I have my suits, jackets, and trousers made for me that wasn’t always the case. But even when I was a low paid Researcher I still had a lovely wardrobe of bespoke suits because I cheated. Mine were vintage suits, some from Savile Row, but they fitted far better than any off the peg suit I could afford. Of course your wardrobe requirements are unlikely to extend to Savile Row suits but you get the point.

4. The Devil is in the detail

The reason for picking some of the pictures above was to illustrate this very point. You can still dress casually and look laidback and comfortable without being sloppy, and it’s the details that make a difference. If we look at Steve McQueen it’s the sunglasses and Tartan lining of his G9 which raises the game. On the chap in the middle photo it’s the belt which ties the look together whilst adding a touch of personality and interest. In the far right hand picture the use of suede and the coloured socks add luxuriance and interest to a pair of ordinary ecru jeans and in the bottom left hand picture it’s not the yellow mac that makes the look but the tie which at once raises the game. In each case a subtle detail uses contrast to make a statement and develop the look beyond the humdrum constituent parts.

These rules apply no matter the type of clothing or the size and shape of the body in them. In the next post I’ll provide a few specific examples of what would work as a core wardrobe for someone on a low budget and working in a casual dress environment.