WIWT: Working from home

After moving out to the San Francisco Bay Area last week, my daily commute now consists of maybe getting up off of my bed and into the living room. As you can imagine, this doesn’t necessitate clothing remotely approaching the most casual work attire.

Combine this with the area’s tech-startup culture and you instantly find yourself in a completely different mindset from when you have to get up, get dressed, get on a train and get to an office building each morning for work in the hustle-bustle of Chicago’s Loop. 

I’ve continued to wear my uniform, however, I’ve shed parts of it. I don’t put on a sport coat or blazer, nor do I knot a tie around my neck. What you see above is what I wear each day: jeans, a blue OCBD, military web belt and socks (if my toes are cold). 

Often, we leave the apartment for lunch and I’ll quickly throw on a pair of desert boots and a navy washed cotton sport coat with a silk pocket square. It’s still casual and gives me the ability to carry my loose items like my wallet, pocket calendar and phones with me around downtown Mountain View. 

It’s not something that would ever get you noticed by a street-style photographer in New York during fashion week, but it’s still stylishly practical for the environment I work and live in daily.

I know many will probably find this extremely boring. It’s not challenging. The pocket square is barely trying to interject a color into a very monochrome palette. Wouldn’t a necktie elevate this look? Why not add a more formal element or two? Anyone could do this!

And, yes, anyone could do this. That’s my point. Creating a stylish look is really simple. You don’t need a complicated wardrobe or to really do anything super “advanced” with color, patterns and fabrics. You don’t need to wear a full suit — or even a necktie — to have a cohesive, put-together look. And dressing nicely doesn’t even have to be a daily practice that interferes with your daily life and morning routine. 

If you’re living frugally on the Ramen Noodle Budget, don’t think you need to wear a new outfit everyday of the month. No one will ever expect you to never wear the same thing twice. Odds are, if they do notice that you wore the same thing twice, then you’re probably dressing a bit too outrageously to the point where people are remembering your clothing instead of you as the person. 

So, realize what you need each day and dress yourself accordingly for your situation. It might turn out that you don’t need much.

Fit details after the jump:

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WIWT: 11-30-2011

It’s the final day of the November of Dressing Nicely (aka, #NoDN) and it’s rather fitting that I actually needed to wear a suit today for work. You don’t really want to show up at a meeting with executives of a potential business partner wearing jeans. It’s also not the time to go over the top with your color, pattern and texture coordination acting as if you have something to prove.

I kept it simple and stuck to the rules: a dark, conservative, solid suit; a solid blue spread-collar shirt; a traditional necktie pattern with only two colors; a coordinating, a pocket square that’s been TV-folded; and black captoe oxfords.

Nothing’s too flashy or out of place, but it’s still a well-coordinated look that gets the job done. I’m a firm believer that if you don’t have to wear a suit everyday, then you can probably get away with owning a simple setup like this and be all right for 95% of what you’d need to wear a suit for in your life.

Get a well-fitting suit, a fitted shirt, a solid pair of leather-soled shoes and a nice necktie — and never worry again about needing something nice to wear on short notice.

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WIWT: 11-16-2011

As stated yesterday, it’s back to the uniform. I had a meeting with a client today, but didn’t want to go for a full-on suit. 

I know I perhaps over-preach my love of this kinda-sorta personal uniform I’ve found for myself, but I never feel bad wearing it. I can see myself easily having a wardrobe full of navy jackets and ties. 

Anyhow, next week I think I’ll do a feature on my wardrobe “essentials” and how I think you can have a full, seven-day wardrobe from just a few elements. Others have done this before, but I’d like to try my hands at it. 

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WIWT 11-15-2011

This wonderful fall weather in the Windy City is allowing for me to continue my rebellious stretch of wearing white denim. This time it’s with a donegal tweed jacket that’s part of a suit.

I should’ve taken a close-up picture, but the jacket has a faint windowpane of blue and rust in it, hence the blue OCBD and brown tie. I need to find a silk square with brilliant orange or rust in it with a paisley design along with some navy to really set this jacket off, but the blue linen works well enough.

Back to the uniform tomorrow!

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WIWT: 11-14-2011

Finally got this jacket back from the tailor last week. It’s a weird green moss-like color in 100% cashmere. Wasn’t really sure what to wear with it for a long time, but I just figured you couldn’t screw up too much using the “Italian Background”.

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WIWT: 11-11-2011

No, I don’t own any corduroy, just flannel, tweed and knits for me.

Yes, it’s getting “cold”, but I think I can still get by without an overcoat — provided I layer with a sweater underneath and carry gloves and a scarf.

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WIWT: 11-10-2011

Decided to keep with the more casual theme again. I actually wore a navy sport coat over this, but took it off once I got to work. I know tennis sweaters aren’t for everyone, but I kind of dig the big V-neck on them. Your mileage may vary.

I haven’t really had to think much before on casual office wear, because I’d long ignored it in preference of the jacket and tie — it’s so much simpler to do! But many of the same principles still apply. You still need good fit and instead of a wardrobe of jackets, perhaps focus on getting a few, high-quality sweaters.

Admittedly, my sweater collection isn’t vast by any means (again, preference for a jacket and tie), but I think some rules overlap with the purchase of jackets. You want something decently constructed from good materials. You want it to fit well. And you should be aware that different sweaters can be made of more casual or formal material.

Obviously, the tennis sweater’s origin is one of sport, making it a bit more casual than perhaps a merino V-neck, which can find itself more formally layered under a suit at times.

I’m still an advocate for the jacket and tie, however, I do recognize that it’s not for everyone out there. If you find yourself in that situation, then maybe start giving a lot more thought into sweaters and making them a part of your wardrobe.

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WIWT: 11-09-2011

I’ve been stretching to do more casual stuff lately. It’s a bit of a change for me, but it’s not exactly difficult to do.

If your workplace (or lifestyle) is denim-friendly, then it’s pretty easy to fall into the slump of throwing on a button-down collar shirt (left untucked) and call it a day. Instead, try to go for a bit more cleaner look — least in the colder months when you can make use of layers.

Tuck in the shirt, throw on a sweater (or in this case, a sweater-vest) and select a jacket made from a more casual fabric — like tweed, cotton, corduroy or moleskin.

Neckties aren’t necessary (gasp!), but get yourself a nice silk square with a pattern or design on it for a slight bit of sophistication.

To really anchor this down though, get a great pair of shoes. Denim and brown brogues will look fantastic. It’d be tempting to go with more casual footwear, I know, but don’t. If you don’t typically wear your “nice shoes”, then here’s a chance.

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