3 Strategic Suggestions For Your Thanksgiving Look

Style > fashion for Turkey Day. No hard pants allowed.

I do not have many rules for Thanksgiving other than I will make scratch cornbread for the same stuffing recipe I’ve been making for the better part of a decade, and I refuse to look sloppy or feel uncomfortable. The latter is much harder to execute because finding an outfit that is comfortable enough for the long-haul slog of cooking and allows you to eat without restriction and looks polished? Well that, my friends, is a hat trick. 

But it does exist, and I think we should talk about some of the options today, since we have almost two weeks to decide on the perfect outfit. (Full disclosure: This is not a big fashion holiday for me. For this dinner, I’m not trying a new trend or reinventing my personal style. We’re going for easy, not groundbreaking.)

Everyone has different needs for their Thanksgiving outfit, but my requirements have remained the same for quite some time. I prefer something that is machine washable, as making a big feast is stressful enough without having to worry about whether or not you ruined your outfit with a splatter catastrophe. In a perfect world, I’ll wear something that camouflages any spots from cooking, kids, or food spills, so a dark print of some kind—ideally an autumnal floral—but that’s not required. Additionally, the look for this holiday also cannot feel constricting. I love a structured garment, but not for Thanksgiving. Not when pie is involved. Hell no.

So where does that leave us? Well, I’ve thought through three possible options for you today, and I hope one of them lands. If you have other thoughts or suggestions—or excellent recipe suggestions; I’m looking for a good gravy recipe, if you have one—please leave them in the comments below!

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Option 1: Smocked Frocks

There are a few brands that really excel at smocked dresses, though they’re obviously available across a wide range of stores and price points. Doen is always at the top of the list for me, and I own a somewhat startling number of the brand’s easy cotton dresses. My favorite one right now is the Bijou Shirred Floral-Print Organic Cotton Poplin Maxi Dress ($350), as I love a dark floral print always, and especially at Thanksgiving. There are additional sizes at Saks, too.

I’m also a fan of what the team behind La Ligne is doing, and the brand’s iteration of the smocked frock—the Phillipa Dress ($395)—is really nice. The dark cranberry color is festive without being too on the nose, and the front-tie bodice offers a tiny twist on this standard shape. (Also off topic: La Ligne’s Sequined Tulle Midi Skirt ($325) is currently sitting in my shopping cart, and I think you might like it too.)

Hill House Home is another beloved brand for the nap dress trend. Preppier girls should check out The Ellie Nap Dress ($150) in white tartan, and I like The Ribbon Ellie Nap Dress ($228) too, which will work well into spring.

The slightly cooler version of this look is a smocked dress with a dropped waist. Unsurprisingly, Doen has a great one; the Bellamy Shirred Printed Cotton-Poplin Dress ($300) is prairie perfection, though I’d toughen it up with my favorite moto boots. Rachel Comey’s Mica Dress ($650) is another easy option. It’s sleeveless, so if you live somewhere cold, just throw on a long-sleeve bodysuit underneath. If you require a dress with a sleeve, try Apiece Apart’s Tuva Maxi Dress ($485) in Dutch Floral, which ticks all the boxes.

Don’t ask me why I’m barefoot in the street, but here’s my go-to Thanksgiving dress for reference. Yes, it’s Doen, and normally I style it with a vintage pair of saddle-colored suede boots.

Option 2: Trapeze, Please.

If a smocked dress makes you feel like you’re doing Laura Ingalls Wilder cosplay, and you’d prefer something even simpler, perhaps consider a modern kaftan?

My dream dress for a more formal Thanksgiving? The Aurelia Crepe & Satin Maxi Dress ($180) from Banana Republic. In addition to being a chic choice for anyone, it’s also excellent for those of us who really like to eat, thanks to its elegant trapeze silhouette. (It would also be a smart choice for hiding your shape if you are currently pregnant and not ready to talk about it.)

Another style that caught my eye? The Asymmetric Tortoiseshell-Print Dress ($175) by Cos. I’m a sucker for a black/brown tortoiseshell, and this swingy shape will look refined even whilst shoveling honey-baked ham into one’s mouth. 

While more of a slouchy silhouette than a full-on trapeze, I also love Raey’s Recycled-Yarn Cotton Blend Sweatshirt Dress ($355), which could quite easily be dressed up and made more trend-forward depending on your shoes and jewelry. In fact, I recommend checking out everything Raey makes; it’s the in-house line for Matches Fashion, and has never disappointed me. The Panelled Silk Satin Full Slip Dress ($565) is another good option.

For a colorful fever-dream designer iteration of this shape, I’d like to point out that La Double J makes a beautifully swingy Magnifico Dress ($1490) that you could layer over tights and suede over-the-knee boots for now, and wear with strappy flat sandals on warm-weather holiday. I also like the Georgio Dress ($1050) from Bernadette for that same reason. 

The Banana Republic dress! Shockingly chic for the price point.

Option 3: Perfect Pull-On Pants

For any readers who are Team Pants for life, I have a few extra-easy options for you. First and foremost: Frame’s The Jetset High-Rise Flared Jeans ($230). They have a cult following, thanks to their thoughtful design that’s just as ideal for travel as they are for Thanksgiving dinner. Yes, they’re technically jeans, but they don’t have zippers or buttons or pockets, and the denim has some serious stretch, which makes them excellent for this occasion. 

Fashion insiders are wildly fanatical about High Sport’s Kick Cropped Stretch Cotton Flared Pants ($860), which are much more of an investment, but never lose their shape, and last and last and last. They’re also fastening-free, and have a high rise, decent stretch, and a cropped length. 

As for styling, you have options galore. I am still in love with Gap’s 24/7 Split-Hem Turtleneck ($63) in black and white breton stripe, which I highly recommend and wear with my Frame jeans on a regular basis. I also am mad about my new J.Crew Cashmere Shrunken Crewneck Sweater ($148) in Black Heather Camel Stripe, and a Sezane Chlo Shirt ($125) in black guipure I picked up last week.

Bought this J.Crew sweater last week and totally smitten.

As always, if there’s an item you’re shopping for or you need help sorting through the zillions of options out there, please don’t hesitate to drop me a comment and I will add it to my to-do list. (And why am I prompting you to comment? Because while I love DMs and always try to answer you there, my inbox is messy, and comments here are much easier for me to find and use as source material as I’m working on new things. Also, I love comments; they make me feel seen.)

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Okay friends, that’s it for now. If you want to follow me on @hillarykerr, I’d love it. And if you have anything to say or ask (preferably nothing terribly mean), please drop me a note either via DM or in the comments below.

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