The Thought Process of Packing for a Weekend Away

Note to self: remember toothbrush this time


I’m going to Southampton this. I’m taking a Jitney to get there which means I’ll want to pack light because I’ll probably want to walk to the stop, which also means I can’t take the box of container tea on my kitchen counter because it’s brown and muddy and seems like an unlikely pairing for a bag full of white stuff.

Do I have plans for the weekend? LOL.

Will I leave the house? Maybe. Once. On Saturday morning, likely to buy basil because I know my mom won’t tell me that she hates my guacamole, which is more of an Italian e-guaque-molé than anything else. What does one wear to go to the supermarket, you wonder? Black tie casual, of course. Assume that on Saturday I’ll want to wear nothing but a bathing suit and button down shirt over it. I left a good striped linen one from J.Crew behind last weekend. No need to re-pack that. And then I’ll take that lilac Lisa Marie Fernandez one-piece with me. Maybe the combo will make for another opportunity for the Instagram community to tell me I look pregnant. You know what, I’ll re-do last weekend. No need to bring anything new. I’ll wear the white sandal-Scholl’s again and call it a look.

So what am I doing Friday night? Probably dinner at home + my parents’ friends. Do we have anyone over? UPS hasn’t delivered a thing in months — I haven’t seen Cool Dad Keith in a while. I wonder what he does on weekends. It’ll probably be a bit chilly. Maybe the capris with a white button down shirt. Or khakis with a silk tank top so that I can wear a whole bunch of necklaces and a utility jacket. But do I really need a jacket? I’ll just take a sweater. Maybe that new ivory one from Madewell. I’ll wear one of my dad’s sweaters. That’s settled, okay.

And it’ll look great with white jeans. I think I left a pair there. Okay. No culottes, no button down, no khakis, no necklace. Easy.

Oh! But what about that red linen midi skirt? Nah. Not modern orthodox day school teacher doesn’t feel like role playing this weekend. And shoes? The Scholl’s should do it.

Okay — back to Saturday. What did I do with that Lisa Marie Fernandez poncho that I found on The Outnet last February? What a cool alternative to towels. I’m just gonna pack a couple sarongs too. To wear in my hair? Around my waist? To choke myself with? These should fit in a handbag.

And then what happens Saturday night? Dinner? At home? Out? If we do in fact head out, I should just take and wear that turquoise mini dress from The Reformation. That’ll pair nicely with those suede Gianvito Rossi sandals. Is suede a weird fabric for over there? Maybe clogs are better suited for Saturday night. But do I want to wear clogs either? Something about the dress that–why am I getting so anxious about dressing for the weekend? Maybe I keep thinking of loafers and white jeans and looking like Amelia and that’s not me. Thank heavs! I’ve never even tried a lobster roll. Keep it real, Leandra. Think leather jacket. Oh, oh! How abouuuuut: white jeans again? With a plain white t-shirt? AND A GARDEN GROWN FLOWER IN MY HAIR?

Look at that, I don’t even need to pack a bag.

Background Photo via Louis Vuitton

For more Thought Processes, clicky here. We’re also thinking a lot about wine, specifically rosé. If this makes you summer-ready (because it’s not yet June 21st!), check out our Swimstagram Swimsuit Guide. If the weather’s got you low, you could also dress like Leandra on a rainy-a$$ Tuesday morning.

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