Jake Woolf
@jakewoolf
Homemade Haute Takes™ are my own, but there are enough to go around
Tomorrow, I’m heading to Italy for the second time this summer. This time is for vacation though, so my packing list is vastly different than it was just a month ago. Here’s all 36 items that made it into my suitcase Link in bio

hey…just calling to say sorry for saying your boyfriend looks like he posts his OAS terry cloth camp collar shirt with a montauk location tag on his IG story
Unfortunately I realized today that I cannot go on living without a vintage Patek Philippe Calatrava So either something reckless is about to go down or this will be my last tweet

Anyone who says Milan is “gray and industrial” has clearly never been to Indianapolis




apparently time travel IS possible— because someone in Milan built a portal that goes directly to SoHo in 2012

found a good fit pic wall in Milan that went nicely with my shoes


Ladies and gentlemen, we found it: I present to you…the single most cursed clothing design of all time

The Row’s newest sneakers are a good indication of the simple sneaker revival that I think is coming in 2026 No crazy colors, no show-y shapes. Just…shoe


I don’t think any single outfit has influenced my summer style more than the one on the right in this photo from take ivy a loose oxford shirt, just above the knee green shorts, and loafers will never not look good (assuming you dial in the *right* version of each)

one of the most polarizing shoes of all time some people, like me, found them to be wearable torture devices others, including members of my own family, raved about how they felt like an all day foot massage
Sale season is here, which means it’s an excellent time for DEALS on all sorts of summer shoes like loafers, sneakers, and sandals Here I poured through hundreds of e-commerce pages to find the 25 pairs of discounted shoes that you’ll actually want to wear long term Link in bio




You ever see a pair of shoes in a sale section that are so ugly, poorly made, and trend-chasey that it causes an existential crisis thinking about how many resources were expended in their creation, only for them to end up as a sub $50, soon to be landfill inhabitant? Or just me