Tee, Brixton // Shirt, Gitman Vintage // Blazer, Acne // Belt, Epaulet // Bag, Archival // Jeans, Levi's Made & Crafted // Shoes, Tretorn // Hat, Supreme

I recently took a job with Svpply, a startup in NYC.  I’ve written about Svpply previously – it’s a fantastic company filled with fantastic people. Last week, one of our co-founders, Zach Klein, pointed me to this question on Quora: “What can a man wear in Silicon Valley business circles to be impeccably dressed with out being overly formal?”

While I’ve never been to Silicon Valley, the underlying anxiety here is something that I’ve seen nag at men in the creative fields everywhere.  In six years, I’ve gone from small ad shop, to digital strategy firm, to start-up, all of them companies founded one way or another on the idea of doing something unprecedented. The normal sartorial rules of the workplace are irrelevant here, so what’s a guy to do when there’s no suit and tie to fall back on?  Taking from my experience of working with whole cast of entrepreneurs/creatives/internet-makers, here are a few things I’d suggest:

1. Fit, Quality, Comfort…and Utility

First of all, no matter what, dressing well is built around fit, quality comfort and (in this case) utility. It is a complete waste of money to buy things that do not fit you, that are not made well that are uncomfortable or serve no functional purpose. Do not buy anything that does not check these boxes, you will regret it. (Also, functional does not mean sports/workout gear. Mesh shorts, like sweat bands, are only considered functional in the gym).

2. Invest (really invest) in a bag.
This is the most important item you own – you use it every single day so it needs to be as useful and durable as possible. Beware the messenger bag. They can be sloppy and bad for your back. Go with a tote or an informal briefcase.  A good backpack is completely acceptable as long as you cannot imagine a high school kid wearing it.

Suggestions: J.W. Hulme, Archival (above), Filson, Kelty, Skinny Vinny, Billy Kirk, Wm. J Mills & Co

3. Three pairs of shoes will go a long, long way.
One pair canvas, one pair leather and one pair boots. Formal shoes aren’t a must, but no matter what, each pair should look as good with jeans and a T-shirt as they do with chinos and a blazer.

Canvas: Tretorn (above), Converse, Zuriick, Vans // Leather: Epaulet, Alden, Common Projects // Boots: Wolverine, Red Wing, L.L Bean

4. One blazer. Uno. Ichi. Eins.
For those rarest of occasions, or if you feel like being spiffy, just one will do. Navy or grey but I advise against black as it can be too formal. I’d say an unstructured blazer (like above) will get you far.

Suggestions: Oliver Spencer, Gant, J.Crew, Steven Alan, General Assembly, Acne (above)

5. Graduate from (just) T-shirts.
Basic tees are important. About ten plain shirts in a combination of black, white and gray should do it. On top of that, it is ok to keep your old ones with sports teams or bands on them – that’s charming and cool in a kind of Street way, but do supplement with about five button downs.  I suggest a range – a couple solids, a couple patterns, in varying weights and at least one white.

Suggestions: Gant, Gitman Brothers Vintage, WWM, Thom Browne, Ralph Lauren

6. Half of your pants collection should be exceptionally high quality.

Pants get the biggest beating. Half of them should be able to last through the apocalypse and fit slim (i.e. do not puddle around your ankles or sag in the butt). Pants that look good and last for years are worth every penny. Plus, everyone loves a guy in five year old jeans. Means he’s crafty and dedicated.

Denim: Tellason, Raleigh, APC, Levi’s (above), Nudie, Rogue Territory // Non-Denim: Bonobos, Epaulet, Outlier, Dockers

7.  Hang on to your North Face, but have at least two other options.

In my experience entrepreneurs tend to be outdoors-men, (aspiring or otherwise), so waterproof/outdoorsy jackets are fine and necessary.  That said, make sure you have others that are not made for mountain scaling as you do not need to scale mountains while in the office.

Outdoorsy: for when you need to be all active outside.  Like this one.
Light jacket: not denim and can fit a sweater under it. Like this one.
Heavy jacket: should keep you warm. I suggest wool. Like this one or this one.

8. Rule of four layers
Thinking in layers helps you understand how many pieces you need/want. The idea is you need (roughly) one layer for Summer, two for Spring, three for Fall, four for Winter.  Like so:

One Shirt (Tee or button down) = Summer
Tee + (Button down or jacket) = Spring
Tee + Button down + (Jacket or Sweater) = Fall
Tee + Button down + Sweater + Jacket  =  Winter

With ten basic tees, five button downs, three or four sweaters and three jackets you can start to see how your options multiply. (Bonus points if you write a program that will create those combinations for you).

Tips on sweaters: go with merino wool, cashmere, cotton or a blend.  No synthetics – they make you sweaty and don’t actually keep you warm. I like ones like this and this.  For casual, hoodies are good perfectly acceptable. Like this one.

9. Ties
Not a must, but they make it easy to look slightly more dressed up and they’re just fun. I’m actually partial to the tie and sneaker look, these days.

Suggestions: Graham Withers, The Hill-Side, The Windmill Club, Pierrepont Hicks, Alexander Olch

10. “Every day, wear something that says something about who you are”- Put This On
Most importantly, have something that lends character and that you love wearing. Examples I know and love include big watches, bow ties, blue hoodies, red belts, and bad ass hats. Whatever it is, find that thing, big or small, and wear the hell out of it. The last thing we need is a sea of ‘creative professional’ clones wandering the earth. Plus, when you get all famous for building the internet, we’ve got to have something endearing make fun of you for.

**Editor’s note**
This post is inspired entirely by the gentlemen I’ve had the great pleasure of working with.  They’re my friends and comrades and I respect them deeply no matter what they wear. They could all show up
to work in garbage bags and I’d still congratulate them on being the talented men that they are. And that’s the truth.

  1. unitedstyle says:

    I thought this blog was on permanent hiatus?! Nice suggestions, but I'll put in my 2 cents and say skip the backpack. You're not in school anymore and you're not jetting off to hike the Rockies. That said, the Archival bag is pretty nice.

  2. M says:

    haha, I know, me too. It's been two months, gotta get back on the grind?I hear you on the backpack, but for guys carrying computers and gear with them everywhere, (through airports and cabs and stuff) backpacks are the best for your back and travel.

  3. I have to disagree with you about bags. I realize your suggestions are aimed mainly at a youngish audience (and at 48 I may be something of an outlier), but I would not be caught dead with either a backpack or a tote bag. I've used messenger-style bags for 25 years, and never had a sloppy-looking one in the bunch. I've avoided potential back issues by being aware of how much I'm carrying in my bag.

  4. M says:

    @some assembly My suggestion on backpacks is also in keeping with the Renaissance they've seen as of late. At one point backpacks were reserved for punks but times change. Give them another chance, there are some good ones out there.

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