Goods for Gathering: Fall Entertaining with Monogram Mary & Habitual Hostess

As the air turns crisp and calendars fill with Fall gatherings, a well-set tablescape and festive setting is more than a 'grammable picture—it's a place where warmth and connection come to life. We asked three women who know a thing or two about stylish hosting—Brooke Shepard of Monogram Mary and Alston Calabrese and Leigh Hansen of Habitual Hostess—to share their favorite ways to make the season's entertaining effortless, elevated and personal.

Q. Walk us through your go-to fall tablescape. What are the essential elements you always include?

Brooke: I don’t always follow the traditional path—if you’re a colorful person like me, let your palette reflect that joy. Don’t fall into the trap of creating something that doesn’t feel like you. People remember authenticity—and I love using a guest towel as a napkin so everyone leaves with a little keepsake of the night.

Alston & Leigh: We love incorporating seasonal touches like gourds, pumpkins and Fall foliage. Big branches and acorns are beautiful and budget friendly, too. A touch of colored glassware in burnt orange or amber adds warmth and makes any table pop.

Q. What's an amazing make-ahead recipe or entertaining hack that lets you actually enjoy your own party?

Brooke: My favorite trick—which I actually learned from Alston and Leigh—is to batch your cocktails ahead of time so no one’s stuck playing bartender all night.

Alston & Leigh: The batched cocktails are actually our number-one rule! And get yourself ready at least 30 minutes to an hour before guests arrive so you're all set to mingle.

Q. How do you create a warm, inviting atmosphere for fall gatherings without a huge investment?

Brooke: I mix what I already have—garden flowers and my grandmother’s platters that always spark a conversation. A monogrammed napkin ties it all together. If you can only have one set, choose a color that works across seasons, like green—it pairs beautifully with summer blues or Christmas reds. Most of all, relax! If you’re calm and happy when guests arrive, they will be too.

Alston & Leigh: We love hosting a simple ‘Soup & S’mores’ night. Soup is inexpensive to make and it's usually better if you make it the day before. S'mores are a fun activity and sitting by a fire pit is always warm and inviting!

Q. What's one entertaining "rule" you've broken or ignore completely?

Brooke: Perfection. Remember, no one else notices those little things you're obsessing over. I believe in imperfectly beautiful moments filled with laughter, kindness and connection—that’s what people remember.

Alston & Leigh: To us, it's really about embracing the right details—the ones that make an event or hosting moment stand out and feel special. Things like monogrammed napkins, a memorable speciality cocktail, great lighting and a well-curated playlist.

 

Q. What's your favorite fall entertaining memory, and what made it special?

Brooke: Fall always reminds me of my grandmother, Rosie. As the holidays approach, I think of how she never let anyone spend a holiday alone—she’d even invite my classmates who didn't have plans to her Thanksgiving table. I love reusing her designs since I can’t quite recreate her cooking (pretty sure she added butter to everything!).

I recently hosted an event using one of her owl designs, and it might be my favorite table yet—the colors, the patterns and the people. She taught me that the best tables are filled with kindness, laughter and room for everyone.

Alston & Leigh: Some of our favorite memories are from Alabama (our alma mater) football game days—bringing our Southern friends together and serving up favorite Southern treats. Nothing beats that mix of comfort food and great company!