Dresses That Deserve Dinner Reservations
Updated: Aug 28
I’m a big fan of “buy the dress now, then you’ll find the reason to wear it.” Some people make plans, then run out shopping in a frenzy to find something to wear. For me, the outfit inspires the plan. I buy the perfect going-out dress? I will be going out later that day. My rain boots are so cute I’ll opt to walk in the rain just to take them for a spin. I love clothes, and I love finding reasons to wear them.
So, here are the dresses that would have me making dinner reservations on OpenTable as I’m leaving the store.
This dress is absolute perfection. Simple enough to rewear and style countless different ways, yet striking enough to get endless compliments. I love a piece that’s a conversation starter, and as a personal fan of Dauphinette, I’ll take any excuse to start that conversation.
To me, this is most definitely a piece I’d get stopped and asked, “Where did you get that?” The color is striking, but the simple silhouette and fabric mean I could still rewear it time and time again. And two personal favorites: the square neckline (it’s so hard to find the perfect square neckline) and the mini length.
It’s balanced enough that I could keep it young and fun with knee-high boots or pair it with kitten heels and a linen trench for a more polished daytime look.
Okay, so this one’s not technically a dress, but as a matching set, it has the same ease and drapes beautifully when worn together.
Production Mode also has a Chicago storefront that’s worth stopping into anytime you’re nearby. Not only does the owner, Jamie, collaborate with countless artists as she creates her own pieces, but she also carries a rotation of incredible designers. So while you may go in for this silk set, there’s a good chance you’ll leave with something else you weren’t planning on buying. Which, obviously, I support.
My current obsession is Melke’s fishing-inspired collection. I have been loving so many recent pieces of theirs, but this dress stands out for its unique print and immense wearability.
This is a dress I could throw on with minimal styling, and it already looks complete. I’d add a pair of heeled loafers for a fun office look, then slip into kitten heels for dinner after. I love a dress that can do both.
Although I typically think of Damson Madder for more casual daytime pieces, I absolutely love the Carmen Ruffle Dress for a chic date-night look.
Typically, when I want a “go-with-everything neutral,” I opt for chocolate brown over black. I think it’s more interesting and a bit warmer. I also love the way a pink shoe can still pop against brown without immediately becoming the entire focus of the outfit. With black, I feel like the color becomes the statement, while brown lets the two play together a little more.
So, when you want to throw on a simple black slip, maybe opt for this chocolate brown number with a little texture instead. Just as easy, but not as boring.
This color is just stunning. I love a good chartreuse, and the combination of that with the silky fabric, high neckline, and draping is an immediate yes for me.
As much as I enjoy styling, I love having a few dresses in my closet that make a statement on their own and require little to no styling before walking out the door. To me, the neckline, sleeves, and draping are interesting enough that I wouldn’t feel like I had to add much in the accessories department. A great shoe and a little bag, and you’re done.
While these are some of my current favorites, two of my favorite dress brands to shop for secondhand are Fuzzi and Komarov. Fuzzi is much easier to find secondhand, and honestly, every piece I have from them is beyond flattering. Komarov is a bit harder to find, but I promise it’s worth scouring eBay for.
And as always, I love a vintage dress. I also secretly love saying, “It’s vintage,” when someone asks where it’s from. AKA it’s mine and you can’t have it.
So, if you also love a good one-of-one find, check out our Chicago Vintage Store Guide.