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How not to dress for success.

Q: What is that you’re wearing? Is that a Speedo and a cardigan?

A: Four weeks ago, I boarded a flight from New York to San Francisco for a two-day photo shoot with two laptops, a paperback copy of Harry Potter and the Order of the Phoenix, and any clothes that fit in the remaining space in my backpack. Of course, being thisclose to Portland from the Bay Area, I’d added a weekend stopover to my trip. And so, on Friday March the 13th, I left San Francisco for Portland for what I thought was going to be just a Saturday-Sunday joyride before catching the redeye to JFK Sunday night. 

Obviously, we know how the rest of this plays out. I’ve not been back to New York since. 

This is, of course, about as lucky as a guy could get in the face of a global pandemic. I found myself already in Portland, with my family, when the numbers really began to escalate. I did not have to fly back into the epicenter of the Coronavirus universe only to try to find my way out again. And I had everything on me in order to continue to work remotely. 

Well, almost everything. 

Four days of clothing. Given that’s all I thought I’d need, that’s about all I had in my bag. A few rolled-up pairs of underwear, some socks, a few T-shirts, a zip-up fleece and some running stuff. After all, sweaters are bulky and you can just keep wearing the same pair of jeans and no one will notice, right? 

Only now, people notice. The few people who actually see me on a daily basis notice everything I’m wearing because I’m wearing it so damn often, and they’re seeing me even more than that. I had some clothes at home in Portland—but they’re mostly out-of-season things and old sweats that harken back to a time in my life when I dressed like I was a four-person tent. 

So I’ve had to get creative. And because I’ve had to get creative, and because I like to make an ass out of myself and document it for others, I have taken my wardrobe, my current situation and a pair of shoes and created my own personal working-from-home style guide, complete with stories behind each “outfit.” It probably won’t spark any ideas for you. But that’s not really the point.  

Because everything seems so difficult these days, I’m showing up late, with both Monday and Tuesday in hand. That’ll change as of Wednesday. Thanks for your patience. It shows you care! (Or that you don’t, so much, because this is really a pointless and ridiculously frivolous exercise!)

5 Days, 5 Ways to Style the GrandPro Rally: Working From Home Without Most of Your Clothes Edition: 

MONDAY: The one remaining pair of clean socks goes perfectly with a sweatshirt you stole out of your son’s closet, and that pair of basketball shorts you painted the trim in.

TUESDAY: The last time you spent this much time indoors surrounded by your family? The holidays. Happier times. Okay, okay: less terrifying times. Why not try to bring back some of that magic, by dusting off those expensive novelty reindeer pajamas that  the whole family wore for that one picture before shoving into the very back of their closet? Pair it with a white button-down and a wool crewneck—because you read in Refinery29 that getting dressed up would be a sure-fire way to keep you from feeling so f#cking sad about all of this.

Coming tomorrow: Wednesday!



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