Style Dilemma: Finding the Grownup Overnight Bag

This is my dilemma, folks. Usually, Style Dilemmas come from readers and friends, or even from family. But in this case, well, here’s my story.

In January, H had his Big Company Holiday Party at the American History Museum. It was a crazy time, and I’d barely thought about what to wear. Fortunately, both of the dresses I bought for his reunion were an option. Nor did I need to think about shoes. The I-Could-Wear-Them-Every-Day Stuart Weitzman patent platform pumps I bought for the reunion (a more than worth it investment I’d recommend you consider) worked for both dresses.

So we could have a little alone time, H booked the night at The Willard. We certainly don’t live far from downtown DC, but not having to worry about what time The Beans would wander into our room (invariably early, when we’re out late)? Heaven.

We were late, we were rushed. I tossed my shoes, underwear, and next day morning clothes into my gym bag. It’s the smallest thing I have. The dresses went in a leftover store garment bag.

We ran out the door and hopped in the Uber. I mean, if we’re going to stay at the Willard, we should arrive in style, right?

We pulled up, and the doorman opened the door. I stepped out, and our driver handed me my bag. And then I went to walk through the lobby at The Willard. With my gym bag. I decided right then and there I need a new overnight bag. Well, I need an overnight bag, because a gym bag doesn’t count. I’m a nearly-40-year-old woman who counts herself among the relatively stylish (presumptious, I know), and my bag looks like I’m in high school.

Thank you, Mr. Bellman, for snapping this before we stepped out to party with Kermit, Dorthy's ruby slippers, and the American Flag.

Well, I still haven’t bought one, but I’ve thought about it. Often. And on the eve of my BFF’s 40th, when I’ll drive north to PA to celebrate with her for one night, I packed, and again I wondered which bag to use. My trusted and reliable L.L. Bean rollerbag is too big for a t-shirt, shoes, a dress, toiletries, and a sweater. Oh, and a clutch. I won’t be able to find a solution in time (gym bag, you win again), but I searched out a few small, stylish, and hopefully durable options.

Herschel Novel, Rib & Hull Heirloom Tote, Adidas Perforated Hold All (yes, I know, no gym bags, but this is a decidedly grownup one. Picture yourself arriving for an overnight in a hipster hotel on the LES, perhaps?), Graf & Lantz Carry On

What do you use for overnight or weekend trips? Do you have a favorite? Do you use a garment bag? Toiletry or jewelry cases? Please share!

Oh, and yes, I wrote this post, then remembered...I’d posted on a very similar dilemma not all that long ago. We’ll just blame my memory loss on The Beans