8 Thanksgiving Travel + Dinner Outfit Suggestions
None of which are in burgundy, cranberry, or wine*. Ahem.
Hi everyone, and thank you for joining me today.
To be totally transparent, I’m struggling with writing this newsletter right now. I can’t pretend that everything is normal, and I won’t sweep my sadness under the rug. While most of this week I’ve been in a state of functional freeze, yesterday I donated to the ACLU, Planned Parenthood, The Loveland Foundation, and Lambda Legal. It’s not comprehensive, but it’s a start.
I also know that sometimes I need a momentary respite from the news and the fight ahead, and truthfully writing this newsletter gives me much joy. So here we are.
Today, the distraction I’m allowing myself is to think about what I’m wearing for Thanksgiving. Pre-kids, I made it a very elaborate celebration with loads of guests, multiple options for every dish, and a multi-day process for setting the table. I don’t have the time or energy at the moment to go so hard, but I still look forward to seeing my family and doing some serious cooking. Of course, the meal is only one part of the holiday, so let’s talk about all the looks to think through, whether you’re traveling or hosting at home. Also, for the record, this is not a dramatic fashion moment for me. The cooking, decorating, and family time are front and center for me, so this is not going to be a trend-centered story. No shade; just saying.
PS: For those of you who were part of the sleeping undies convo, wanted to let you know that I bought the Negative boy shorts you all recommended, and they are excellent. Like, ruined me for all other underwear, excellent. I bought them in black in a medium, and they are heavenly. Maybe run a smidge big? Which I don’t mind. They don’t cut in on your sides at all and are so insanely soft, I never want to take them off. I’m writing from bed wearing them right now, with the matching black long sleeved shirt (which 1000% could be worn outside the bedroom; I’m going to wear it with a leather skirt to dinner, but it would look great with jeans, silky trousers, or even layered under a short-sleeved dress.
Four Travel Outfit Essentials
As I’ve mentioned many times, I HIGHLY recommend Nili Lotan’s Shon Pants ($375) for travel. They are so soft and easy to wear; truly the opposite of “hard pants,” though they look polished. I wore them more days than not when I flew to the east coast this summer to see my husband’s family, and they work equally well on a plane or relaxing by a fire.
I have the super soft black cotton-twill ones, but they come in a bunch of colors and now in cord too. I have a size 6, but they run big, and I could have done a size or two down, but personally I prefer a looser fit. While they excel at travel and relaxed days, I do think they could dressed up for a more casual Thanksgiving if so desired.
If you want the best, softest pant for car travel/general travel/house lounging, I really cannot recommend The Great’s The Jersey Crop ($145) enough. I live in these drapey dreams and have them in a variety of colors and sizes. You cannot go wrong, and I will be wearing mine the whole long weekend. I’m also eyeing the brand’s dark green cropped cashmere pants, which are calling my name.
Finally, I also have my eyes on Ref’s Olina Knit Pants ($128), which look really elevated in navy. Because let's be real: elevated pajama pants are exactly what this moment and holiday travel call for.
I also like a slouchy cotton sweater for travel because cozy + washable = ideal. I have been wearing the hell out of Gap’s Oversized Boyfriend Sweater ($39-79.50), which brings me great comfort in stressful times. I have an olive green one from earlier this fall, but the other neutrals are good too.
Four Easy Options For Thanksgiving Dinner
As always, the strat is: No hard pants, no hard clothes.
Dark Floral Dresses
Smocked dresses in dark floral prints (yes, I’m talking primarily about Doen, like this style) remain a no brainer, as they are machine washable, expansive, and just low fuss all around. I like mine paired with super soft Jamie Haller loafers (the suede ones are lovely) or the affordable velvet mary janes from Paris I wrote about earlier this year.
Pull-On Skirt + Simple Sweater in Seasonal Colors
Those shoes options all work with my other year-round outfit combo: A simple pull-on slip skirt—pleats will show fewer spills if you’re a messy eater/cook like me—and a cardi or crewneck sweater. To make this feel a little more intentional than my usual all-black everything, I like a seasonal monochromatic color scheme. I’m packing a Quince Washable Silk Maxi Skirt ($70.90 on sale now) in Forrest Green, my go-to cashmere sweater, and similarly hued velvet shoes.
Silky Pants!
I’m also packing something you might not expect from me: PANTS. Yes, like I mentioned before, right now, I am feeling quite fond of silky trousers, again, something akin to a dressy pajama pant, especially in a darker jewel color. Matteau comes up a lot in conversations with fashion friends; the brand makes a wide-leg silk crepe pant in a dark floral that’s great. I also love Dries for all things pants, and very much admire this brown houndstooth washed satin pair. The formal print and the slouchy style are a nice juxtaposition. I also like Leset’s version of the trend, which has an extra wide leg and looks a bit like a maxi skirt. These trousers all offer the same easy vibes as the linen drawstring pants we all wore two summers ago (and last summer), but in a dressier, seasonal material. I also might have purchased a navy satin version from J.Crew. All delicious options for your holiday season.
Slouchy Sweater Dresses
I love a slightly oversized, shorter sweater dress for Thanksgiving dinners, especially with a soft suede boot, moto boot, or chunkier loafer. Sezane’s Paulie Dress ($230) is dreamy (also available in camel), though I would not style it with the waist bandana in the pics, personally. Favorite Daughter also makes a cool cashmere and wool version and the black is great too. I also have J.Crew’s Relaxed Cable Knit Sweater Dress ($159.50 on sale in camel) in my cart right now because it feels a little French and a lot of effortless. Same for Reformation’s Tate Regenerative Wool Sweater Dress ($278), which is shorter for me, but that’s what Commando tights are for (they never itch, I swear).
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.
As always, thank you for taking the time to read this post. I’m truly so glad you’re here. If you like what you’re reading, please consider sharing this newsletter. (And if you have the time to like it, that would mean a lot to me!) All products mentioned are independently chosen, and some may be affiliate links. Your support is appreciated.
*Don’t be a snowflake about this joke. We are allowed to be sad.
Sending you love. It's been a horrible week.
And seconding that Doen dress. It's my favorite as well. I have way too many versions!
Thanks for writing this, Hillary, and acknowledging the huuuge elephant in the room. I guess we keep Kamala and carry on a la, but it’s hard and sad.