When it comes to hosting, it's easy to get caught up in the details—the tablescape, the menu, the flowers. Which is why we turned to event planner Callista Osborn, Owner and Creative Director of Callista and Company, for expert tips on what truly creates a memorable gathering. She’s spent more than a decade designing extraordinary celebrations, from intimate dinner parties to destination weddings and glamorous galas around the world, and according to her, the best events have very little to do with perfection because the focus should be on how people feel.
In our conversation, we got into the simple hosting secrets that make guests feel genuinely welcomed, the entertaining "rules" Callista is happy to leave behind, and how to create a beautiful summer gathering you'll actually get to enjoy.
You plan some of the most beautiful celebrations in the world, but at its core, what do you think makes people feel truly welcomed?
Feeling recognized. A moodboard of decor is fun to curate, but what people remember is whether they felt considered. A warm greeting, having a favorite drink waiting, sitting next to someone you’ll genuinely enjoy chatting with—those are the things that make guests feel like they belong. Hospitality is less about impressing people than it is making them feel at ease.
Summer is peak entertaining season. What's one thing hosts tend to overcomplicate—and one thing they should spend more time thinking about?
Guest comfort comes before aesthetics. We can spend hours choosing linens or perfecting the dessert, but it is more important that people can actually hear one another across the table, that there is enough shade or warmth, and that there is a spot for guests to place their drinks. The decorative details matter, but only when the guest experience is comfortable at the core.
What are a few simple touches that instantly elevate a casual summer dinner party without requiring a huge budget?
Don’t try to do it all and make one abundant decorative gesture. Instead, line the table with an assortment of candles or a collection of seashells or platters of crudité. There's something timeless about making a table feel abundant without making it feel overly produced.
As someone who's planned hundreds of events, what's a hosting "rule" you're happy to see people break?
That the tablescape has to be perfect. Some of my favorite gatherings are around a collected table with mismatched glassware and chairs pulled from three rooms. Guests can feel the warmth of a real home and appreciate getting to see how you live.
What lessons from luxury events can anyone apply when hosting friends at home?