Dear First name / friend,
Coming to you on Monday as we fly home from a really fun weekend in Chicago with our boys. The weather was perfect, the city was as fun and beautiful as ever, and we got to see their apartments, friends, and spend lots of time with 2 girlfriends. It’s so great seeing them in their element—happy, healthy, and gainfully employed.
We walked all over the city, played pickleball on an apartment rooftop (my youngest and I won 3–0 in matches…not to brag, but 😜).
I have to say, having some female energy in the group was a welcome shift from our usual testosterone-fueled fun. And the girls are absolute gems - inside and out. All around, a banner weekend, and now I’ll look forward to an extended stay for all three in Newport over Thanksgiving.
I was worried it’d be hard having them so far away, but we’re making it work, and it makes the time we do spend together especially fun and special. I loved every second of being with them—but I didn’t miss the mess they manage to generate in about five minutes flat at home—perks of visiting them in Chicago: all the fun, none of the laundry.
And speaking of trips….Whenever I pack, I make myself try on every outfit before it goes in the carry-on. It takes a little extra time, but it saves me from packing things that don’t actually work or realizing too late that something doesn’t fit/look right. I snap quick selfies so I have a reference and know what I’m bringing —no guesswork, no overpacking. And I make sure everything can be mixed and matched if need be.
👉🏼 Pro tip: Do this before your next trip. You’ll thank yourself on the other end.
Read on for what I packed for Chicago…It was just enough without overdoing it.
