How Can I Look Stylish in a Style-starved Industry?

I’m going to work for Microsoft. At Microsoft, they honestly do not 2 cents to what you wear to work. In fact, you could come into work wearing a cape and vibram 5 finger shoes if you wanted to. You could wear a cowboy outfit to an interview.

With a culture like this, I want to “look good” and styled when I get there, but I don’t want to be so styled that I’m just out of place — I just want to look sharp. Do you have any advice specifically for a dress culture such as this?

3 Replies to “How Can I Look Stylish in a Style-starved Industry?”

  1. That sort of office culture is more common than you might think. Don’t worry too much about looking overdressed — in a place like that, whatever you wear for more than two days in a row will quickly be taken as “normal” for you.

    That said, I’d leave neckties at home most days (but maybe stick one in your desk drawer at work in case you get called into a meeting or presentation unexpectedly). Wear nice slacks, a lightly-patterned dress shirt, and a casual sports jacket most days for a look that’s professional but not dressy.

    You can just go with trousers and a nice dress shirt as well, of course, but having a jacket makes a big difference between “sharp looking” and “just another office guy.” Personalized details like pocket squares or decorative belts/buckles and stylish shoes all help make it clear that your appearance is deliberate style as well.

  2. Like what Antonio said in one of his videos, if you want to step up your business casual or casual dress, you need to go back to the 3 pillar’s of men’s style: Fit, Fabric and Style. You can wear grey flannel trousers, a pair of Italian saddle shoes, and a dress shirt could help you look more proper when working. Don’t wear a tie, unless it’s a formal company event or a business meeting. Hope this helps!

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