Every October, it comes up in our meetings to do a “Thanksgiving outfit ideas” post, which I always kinda resist because I think it’s so dependent on your region (how warm/cold it will be), whether you are a guest or hosting, and the level of casual or fancy it is. I always opt for a long, flowy (non-summery) dress or comfy pants and blouse, and everyone’s style and body is different. But I found a few pieces that felt potentially easy to wear for a lot of people and not exclusive to Thanksgiving, obviously. That dress above is the splurge (and what I’ll be wearing), but some of the options below are more reasonable (I tried on so many dresses, y’all, and found nothing worth showing besides that one; I’m sorry!!).

Top | Jeans | Belt | Boots | Beaded Necklace | Gold Charm Necklace

This shirt is one that we’ve seen before, and it’s always a hit (white and airy for summer), but in this dark, rich plum it is just as easy to wear while feeling more seasonally appropriate. There is a lot of detail in it, and can be thrown on or dressed up. It’s roomy in all the areas, but the deeper V breaks up all the fabric really nicely. I’m wearing a small because my store was out of XS (but generally size down in Madewell tops). I kept this size because it was still fine, but would prefer slightly smaller.

Top | Jeans | Belt | Boots | Beaded Necklace | Gold Charm Necklace

Room for so much turkey in there, but also just a fantastic work or date night blouse. The jeans are the boyfriend jeans from Universal Threads, size 2 (size down). They have a fantastic vintage feel.

Sweater | Skirt | Boots | Beaded Necklace | Gold Charm Necklace

Such a great fair isle adjacent sweater over my new faux leather skirt (that is a bit longer than this; I hiked it up). The sweater is soft and chunky and falls/drapes really well and hits at a nice spot.

Sweater | Skirt | Boots | Beaded Necklace | Gold Charm Necklace

You’ll see me wearing this sweater a ton over the next few months (I think it’s a great holiday sweater or après-ski sweater, too). The boots are my new favorite that I reviewed here, in case you missed my comfortable boot review. Again, the skirt is a bit longer than I’m showing (I hiked it up), so it’s more of an above-the-knee A-line skirt.

Sweater | Dress | Boots | Beaded Necklace | Gold Charm Necklace

My best friend who works at The Great got me this sweater for my birthday, which I’m obviously very into. I mean, this is a very good Thanksgiving outfit, albeit very splurgy. The dress is from Doen and was the only dress that I found worth buying that I felt good in. I’m confused about what is happening in dresses right now – everything is either super body-con column (which I don’t love wearing and certainly wouldn’t wear for Thanksgiving) or very cutesy “Little House On The Prairie” (which I like, but less so for fall/winter). Like, where are all the elevated shirt dresses?? BUT this dress in black with little flowers felt not only seasonally appropriate but year-round appropriate. It’s a thinner cotton that Doen does so well.

Sweater | Dress | Boots | Beaded Necklace | Gold Charm Necklace

Now I’m wearing a medium because the waist hugged in the small (which I did not like, especially after eating), so by sizing up it’s drapier, and I just knew I would wear it more. It’s very, very pretty and extremely easy to wear. These days I’m opting for more matching separates, top and skirt. There is such a fine line between too much fabric and not enough comfort. I think this dress (while having a lot of fabric) actually falls to be streamlined, not voluminous (I know I’m not proving that point in these shots, lol). Shout out to those chunky boots that I LOVE.

Top | Jeans | Belt | Boots | Beaded Necklace | Gold Charm Necklace

I love this shirt so much – the collar details, the colorway (indeed it feels very me). Now it’s a thinner fabric, which I like, but I ordered the size 4, and it’s pretty voluminous, so I returned it and will order a size down.

Blazer | Top | Jeans | Belt | Boots | Beaded Necklace | Gold Charm Necklace

I bought this same tank blouse in white for the summer, so when I saw it in chocolate brown, I bought it. I’m wearing it under my oversized wood jacket (which is a blazer, but I wear it more as a fall jacket). The jeans are excellent – mid-rise Mother in the perfect wash, and look at that hem. Boots are my new western booties that I love.

Blazer | Top | Jeans | Belt | Boots | Beaded Necklace | Gold Charm Necklace

If you are tank-shy like I am, this one is great because it really helps cover the area between the armpit and bra strap that I’m usually sensitive about (i.e., it’s more full coverage and comes up high in the armpit), and it has enough detail, pleating, and buttons to just be so easy to wear and flattering, while offering something interesting underneath a more serious blazer.

Top | Jeans | Belt | Boots | Beaded Necklace | Gold Charm Necklace | Purse

Not sure who this lady is, lol, but these are all fall staples for me (that might look a little formal together?). Admittedly, it’s a great, easy-to-wear work outfit. The shirt was only in stock in XXS, so I’m returning to size up to XS (it fits ok but tugs a bit in the chest), but I wanted to show you it since it’s another easy-to-wear fall blouse.

Top | Jeans | Belt | Boots | Beaded Necklace | Gold Charm Necklace | Purse

Same $50 jeans I love and wear weekly. Purse is so versatile and comes in a lot of faux leather colors (and looks totally real, FYI).

Top | Skirt | Boots | Beaded Necklace | Gold Charm Necklace | Purse

This shirt surprised me. I ordered it thinking it would be a great fall shirt, but when I unwrapped it, I judged it immediately, thinking I would look like a pumpkin. I decided to try it on, and especially with this skirt and boots I was like, “ok, this is a solid fall outfit”, and especially good for Thanksgiving since it’s so voluminous and easy-to-wear and yet feels elevated and like you care. The detailing at the top is so good, and it’s a nice-weight linen, so it flows really well, not stiff at all.

Jacket | Sweater | Jeans | Belt | Boots

The prettiest ochre jacket that kinda goes with everything I own. I hadn’t bought a nice-looking wool jacket in a few years, but this one is so pretty, layers well over sweaters, and isn’t too heavy or hot. More of a car coat, with roomy sleeves and a little cropped.

Coat | Sweater | Jeans | Boots | Gold Charm Necklace | Purse

Now this jacket is so cute, but I ended up returning it because I think it might need to be on taller people. It’s such a good colorway and is a great roomy trench, but I think it’s just too much fabric for my frame and was too expensive not to be a “hell yes”. I left it in here in case someone has the right frame, budget, and style for it. It’s Sezane, so of course on their site they make it look so cool.

Sweater | Skirt | Boots | Beaded Necklace | Gold Charm Necklace | Purse

I know you saw this outfit last weekend, but it’s just so solid that I wanted to dive into the other elements. The cashmere crew is so good – I wear it all the time (soft, roomy, thin enough to layer over, on the boxier side so it doesn’t cling or tug anywhere). The skirt has been a sleeper hit, so if you are into short skirts like me, know that this one sits really easily on hips (not tight on the waist, totally flat front) and perfectly straight down, therefore just so easy to layer something more voluminous over top. And then the MVP boots. I’m bringing this on our annual Thanksgiving couples getaway for sure (we drop the kids at Grandparents in Sacramento and go to Napa/Sonoma for two nights).

If anyone has any great fall dresses that aren’t boring, not too tight, not too booby, please share 🙂

*Photos by Kaitlin Green