When St-Germain asked Bobby and I to be their guests at this year’s Jazz Age Lawn Party, we immediately accepted with an enthusiastic “yes!” and packed a picnic basket for our favorite summer event. It’s like stepping into the past, with dapper gents and decked out gals picnicking, dancing to Michael Aranella and His Dreamland Orchestra, sipping on prohibition era inspired St-Germain cocktails and immortalizing the affair with vintage portraits on a paper moon. There are 20s motorcars, antique gramophones, and even a bathing beauties and beaus promenade. Everything about it is exceedingly charming, and Governors Island – just a ferry ride away from the hustle and bustle – is the perfect setting.

Outfit Details:

The WhitePepper sailor dress (on sale)

Seychelles oxford heels (old)

Anthropologie bow cloche

Juicy Couture sunglasses (old)

vintage parasol

(See Bobby’s blog for his details)

Last year, I wore an authentic 20s day dress and practically ruined it because it was so delicate, so I decided to explore the rest of my closet and see what else could work. I’ve also received a lot of inquiries about what to wear to such an event, and the good news is that you probably have something in your closet, already. The key is to focus on the details: silhouette (drop waist), hats and hair accessories (a cloche, turban, a statement headband worn across the forehead), makeup (dramatic and expressive!), and a little something to take it over the top – a fan, or in my case, a little parasol.

At first, I considered a beaded, Gatsby-esque dress with art deco details and my handmade lace jacket, but soon decided it was more suitable for the evening (anyone want to throw a theme party?). My dropped-waist polka dot dress would have been perfect for day time, but it felt more mod than 20s. Still, with the right accessories, it would have worked.

In the end, the sailor dress won. It has a slightly higher waist than the drop-waist silhouettes of the 20s, but the loose fit gives it a similar look – and the sailor details add to the overall vintage feel. The accessories and makeup pull it all together: a bow-adorned cloche, a vintage parasol, and heeled oxfords.

Clara Bow inspired my dramatic makeup – sleepy, smokey eyes and red lips – and I rounded out my brows just a tad, as those were the style, back then. It’s easier and cheaper to pull together a period look when you hone in on the details, instead of doing literal interpretations. Of course, it was even easier for Bobby because this is basically his everyday look – he just added a boater and that was that!

Speaking of Bobby: as some of you know, he’s a barman at both Milk & Honey and Lantern’s Keep, which specialize in cocktails from the turn of the century. He created a special cocktail (above), reminiscent of the jazz age era, with St-Germain. Click over to This Fellow to see his cocktail creation (along with instructions on how to recreate it at home), and see more photos from our day on St-Germain’s Facebook page!