My Deep Dive Into CEO Weekend Wear
Okay, so I got super curious about what big shot CEOs actually throw on when they’re not doing the whole suit-and-tie power move thing. Like, what hides in their closet besides Armani? I figured it’d be all obscure luxury labels and bespoke Italian things I could never afford. Started digging.
First up, I grabbed coffee last Saturday and headed straight for the city park near the financial district. Figured it’s a CEO off-duty hotspot, right? Just camped out on a bench pretending to read, eyes peeled. Spotted a few sharp-dressed folks walking dogs or jogging. Zero designer logos flashing.
Got home feeling kinda stuck. Scrolled through endless “executive style” articles. All talked about “investment pieces” and “quiet luxury.” Blah. What brands? Give me names! Then I remembered Instagram. Searched hashtags like #CEOoffduty and #stealthwealth. Started screenshotting fits like crazy.
This is where my expectations got wrecked. Completely. The patterns I saw:
- Way more Patagonia than Prada. Seriously, so many fleeces and puffers.
- Basic tees everywhere. Not fancy ones either. Looked like Uniqlo or maybe Everlane.
- Simple sneakers reigned. Saw multiple pairs of plain white leather low-tops – Common Projects? Maybe. But also just… clean Nikes.
- Denim was king. But not ripped, flashy stuff. Dark wash, straight leg. Could’ve been Levi’s 501s or pricer Rag & Bone. Hard to tell.
- Lots of understated outerwear. Think L.*-style chore coats or clean Barbour jackets.
Plot twist! Hit up a tech networking thing last Tuesday evening (casual dress code). Ran into that guy – you know, founded a logistics app that blew up? Worth millions now. He was wearing:
- A faded blue crewneck sweatshirt (probably 5+ years old)
- Plain, dark chinos
- Really worn-in brown leather loafers (definitely not new)
Asked him casually where the sweatshirt was from. He laughed. “Old Navy, I think? Just comfortable.” Mind. Blown. Confirmed the vibe.
So yeah, my big realization spending all week on this? CEOs ditch the fancy stuff fast when off the clock. Comfort and simplicity win big time. Forget secret high-end brands; more often it’s Patagonia, basic tees, no-fuss jeans, and shoes that don’t hurt. Kinda wild, right? All that power, and weekends mean cozy fleeces and whatever jeans are clean. Learned way more about practicality than prestige.
