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

Travel in Style: Weekend Bags From Flirty to Sturdy

Oh, more than 8 weeks ago (I know, because that’s when I started pinning possibilities), a reader and twitter friend asked for some help in finding a weekend bag that wouldn’t break the bank. And while it’s well past her beginning-of-September deadline (forgive me?), it’s time I finally put up or shut up on the topic.

It is, after all, nearly the holiday season, when we all travel to see our families.

Yes, I just wrote that.

It’s also the Season of the Fall Weddings. Facebook, twitter, and Instagram are aglow with group shots of brides and grooms at leaf-adorned outdoor alters, group shots of college friends All Dressed Up, and even invites. So I know a few of you need something in which to stow that gear to get you from Friday night rehearsal dinner through nail appointments, the ceremony and reception, and finally the bleary-eyed wedding brunch The Day After.

The original requirements were a not-uncute weekend bag no more than $100. Easier said than done, of course, especially for this vintage-inspired-luggage addict who goes for the leather travel trunk every time. Gorgeous, but ridiculously impractical.

So I found a group of bags - some bigger, some smaller, most under $100 (but a couple of reaches, especially now that they’re on sale. Personally, if I can’t have leather, I want color.

Clockwise, from top left: Land's End Ella Vickers Medium Duffel (um, named after a woman who served as first mate on the America's Cup team? yes.), Dr. Koffer Fine Leather Accessories Chaucer Bag (see? leather. I told you), Urban Outfitters BDG Buckle Tote (the smallest of the bunch, but adorable and versatile), Lipault Plume Weekend Bag (a bit old school, comes in fun colors), Heritage Leather Co. Canvas Mason bag (love the leather and canvas mix for a mildly nautical twist), L.L. Bean Hardshell Rolling Pullman (the whole hardshell thing intrigues me, though I'm a canvas girl through-and-through, plus, well, rollerbag).

On a terribly practical note, I will say this: if you absolutely must have luggage that you need to depend on (and aren’t terribly concerned about the cute factor, though it’s perfectly presentable), go L.L. Bean or Land’s End every time.

After Mom-Mom bought me my first set of luggage for high school graduation (it’s what she did for all 17 grandkids), and my trusty royal blue canvas Land’s End set took me to my years in Austria and Germany (never mind other trips), I can’t say enough about the quality and customer service from each company. We now rely on an L.L. Bean rollerbag, complete with preptastic monogram. I can stuff a weekend’s worth of clothes for both Beans and me in it (though sometimes the shoes have to go in a separate bag). You can’t hurt either brand, but if something does happen to it, both have impeccably easy repair or exchange policies. They’re pricier than this request, but they’re oh, so worth it.

Just pick a color you’ll like - kinda like that tattoo you’re thankful you never got.