Thanksgiving Weekend Look Book with Kayleigh Kay

For me, Thanksgiving this year is all about cool, casual comfort with a grunge twist.

I love the crispness of the weather this time of year, and the easy layers that just seem to come naturally because of it. This year, I’m all about easy-but-chic looks that show off my style personality. I got together with local photographer Kayleigh Kay, who did my first look book back in Fall 2013, to shoot some looks for this family-and-fun-filled long holiday weekend.

Thanksgiving Dinner: Keep it Cool

I don’t know about you, but while I’m normally a total ice cube, holidays often make me warm. I know it’s a combination of a ton of people packed into a room, lots of food, a bit of alcohol, and the work of helping out, and usually, I try to compensate by layering up so that, as I get warmer, I can remove layers. For Thanksgiving, I’ve decided to take it a step farther and plan to wear these Victoria’s Secret Knockout cropped leggings (though if it turns out being too cold for cropped leggings, with this winter-like weather we’ve been having lately, regular leggings would work here too). I shouldn’t have to say this, but I chose leggings because they’re the most comfortable to wear while helping out, while sitting and stuffing my face, and while debating if the food baby can handle another cookie for dessert (the answer is “yes, you’re wearing leggings!”).  To toughen up the bottom half, I opted to wear my burgundy cut out booties, a pair of Balenciaga knock-offs I found at GoJane for cheap. They’re sold out, but there are a couple variations still available. To keep my tootsies warm, I’ve got half-socks on, but black ankle socks work well with these booties too.

Thanksgiving Dinner: Keep it Cool

Despite the lighter bottom layers, there are some great layers on top, starting with a tribal-print tank top. This tank is semi-sheer, and can easily be worn over a nude bra, as it is here, or over a plain black tank for a little extra warmth. Over the tank is a black and white check flannel, which I got a couple years ago at Plato’s Closet. I tried finding a similar one for you, but wasn’t really able to, unfortunately. It’s a slightly lighter layer that’s easy to make warmer or cooler by rolling up or down the sleeves. On top of that is my thrifted H&M trench vest, for a little extra core warmth without too much bulk.

Thanksgiving Dinner: Keep it Cool

I wanted to add a little bit of sparkle, but didn’t want sparkle, so I opted for my fringe chain necklace.  I got this one ages ago at H&M, so it’s no longer available, but Forever21 has a remarkably similar one for under $20 right now, so if you dig it, snatch it up! For earrings I went simple and asymmetrical, with a DIY cross earring shown off on my undercut side. I waved my hair, because it’s easy and I’m obsessed with my Bed Head Deep Waver. Plus, the waves make it so that next-day hair looks great!  I pinned back one side of my hair to show off my undercut a little.

Thanksgiving Dinner: Keep it Cool

I opted for glasses over the weekend because, honestly, they’re just easier than contacts. Plus, with my black Derek Cardigan frames from Coastal and my three pairs from RetroEyeworks, I have enough variety to really change it up over the course of a long weekend. For this look, I went with my black frames.

And of course, to finish off the look, I opted to carry my grandma’s burgundy clutch, which goes well (in an odd kind of way) with my cut out booties. A clutch allows me to keep my phone handy (for pics of the food, the dog, and the fam, of course), have lip balm at the ready (because when you’re eating so much, the last thing you want to worry about is lipstick, right? Right!), and keep any other necessities on hand (like Tums, haha).

The layers here, and the overall flexibility of the look, makes it perfect for Thanksgiving Day. I can be comfortable both in terms of alternating sitting around and doing work, and also in terms of being too full to move after dinner.  And on top of it all, I’ll feel put together and chic, as opposed to feeling like I’m dressed like a total slob.

Black Friday: Shop Till You Drop

Ok, so really, I don’t usually plan to go shopping on Black Friday.  At least not in the “leave Thanksgiving dinner early to go get in line and wait for the stores to open at midnight” sense.  Last year, hubs and I ventured out to the outlet mall in Michigan City, Indiana after dinner, and it’s entirely possible we’d do that kind of thing again.  I can’t remember what we did during the day, but I’m sure it involved relaxing a bit, helping around the house a little, and otherwise taking it easy. So what kind of outfit does one wear to do all of those things? Well, in my case, it involves moto jeans and skulls (what else?).


Essentially, this is a basic jeans-and-tee look, but I’ve rocked it up a little by starting with skinny grey jeans that have some moto-inspired detailing. I snagged them for a couple bucks at Salvation Army, but they’re Forever21, and there are a couple pairs that are similar for sale there right now (these and these). Instead of wearing a plain tee, I’ve pulled out a looser-fit one that has snakeskin-print skulls and a metallic triangle on it, which I got over the summer on sale at Express (it’s sold out, but this one is similar, graphically). Because it’s cooler out, I topped the tee off with my trusty motorcycle jean jacket from Gap, which is quite a few years old. This one is pretty similar though, if you don’t mind the color difference. I half-tucked the tee for this look, because I felt like it polished it a little more. I added a studded beanie cap, which I grabbed at the end of last winter from Target (they have a similar one in black, or one with a puffball on the top if you’re into that kind of thing). I pulled my hair into a side pony, largely because it helped the hat stay on better, and then rocked the heck out of a long chain earring, because why not?  I also opted to go with my matte navy frames from RetroEyeworks for this look.

Black Friday: Shop Till You Drop

Because I can’t stand carrying a big purse when I shop, and I like having both hands free to browse/carry bags/drink coffee, I opted to switch over to a black crossbody. I got this classic-looking bag for Christmas a couple years ago. It’s by Guess, and while it’s not available any longer, this one is pretty similar. I chose this particular bag, as opposed to the myriad of other crossbody bags I own, because I liked the mix of greys and blacks in this one. It read a little sportier to me than, say, my fringed bag that’s about the same size.

In addition to my single chain earring, I opted to rock a couple of leather bracelets on my wrists. I believe they’re all from Charming Charlie at various points in time, but wasn’t really able to find any duplicates. Any cuffs or bangles could work for this look, and while it was warm enough outside when we shot these pictures to push the sleeves on the jacket up, if it’s chilly, I would likely just nix the bracelets alltogether and leave the jacket sleeves full-length.

Black Friday: Shop Till You Drop

For shoes, I decided to go with my Simply Vera by Vera Wang slip-ons from Kohl’s.  While my exact pair isn’t available any longer, these are currently on sale and very similar.  Slip on athletic flats are easy to walk around in, easy to take on and off in case of trying stuff on, and pretty darn comfortable to be in all day.  My feet haven’t been happy with me lately, so wearing flats like this is a must if I’m going to be on them all day.

The ease of this outfit makes it perfect for everything from lazing around the house, to helping with random chores, to going shopping. It’s one of those outfits that’s almost completely mindless in its simplicity, but the details are what make it stand out. Graphic tees, texture, and accessories can really take a look to a new level.

Saturday Night: No More Leftovers… Time to Dine Out

Reality is, in my family there are enough leftovers to feed a small country. However, I’m the type of person that can’t eat the same meal four days in a row, so by the time Saturday night rolls around, I’ll be ready for something other than turkey. So why not get a little fancy and head out to a restaurant for a big greasy burger or something? A sheer maxi skirt gets the 90’s treatment for this night-out look.

Now, normally at this point in the weekend, I’d have washed my hair, but we shot all this in the span of a couple hours, so my waves are still in tact. Let’s pretend I washed my hair and re-waved it, k? Great!

When I was putting this look together I knew I wanted something with this camouflage tee, which I found at one of my local thrift stores (though I can’t recall which one–likely Savers).  I actually struggled with it for quite awhile, because the top is a little on the shorter side and doesn’t hit me right with quite a lot of my pants. But this sheer maxi skirt, from Forever21 (similar here and there’s a lace-paneled one for the more modest ladies here) was cut high enough, and fit me in such a way, that the tee worked perfectly with it. I added some faux garter tights, but could easily add leggings or tights with OTK socks if the weather stays cold.  Some people are totally over the faux-garter tights, but I’m not. I think it’s because I rarely wear mine (I’m afraid of ruining them, so I don’t wear them much).  I got them at Urban Outfitters ages ago, but they still have this pair if you dig the look. I found these as well, which just look like faux OTK socks, and quite like them.  I added a black pleather jacket, layered on some necklaces, and rocked some sky-high heels.

Saturday Night: No More Leftovers... Time to Dine Out

The 6″ heels might be a little much, depending on where we’d end up for dinner, but that’s ok. The skirt is really long on my 5’4″-ish frame, so heels are an absolute must with it. If it were snowy and/or icy out, I’s rethink this entire look, but let’s hope that this arctic cold stays at bay during the holiday weekend and we can all enjoy being outside. Black jeans and my burgundy booties from the first would do here in a pinch, I suppose. This, by the way, is why it takes me weeks to pack for vacations (even long weekends) and why I always over-pack. I’d rather be over-prepared than stuck looking like Bambi on ice in 6″ heels!

Saturday Night: No More Leftovers... Time to Dine Out

The booties, by the way, are Zigi Soho, and are definitely knockoffs of the famous Jeffrey Campbell Lita boot. My husband bought them for me a few years ago on New Year’s Eve, because he insisted on walking into DSW with purse-less me and spending longer than 15 minutes there. I did get them on super-sale though, which was a pretty awesome deal. I don’t wear them often because they are impossible to drive in, so wherever I do wear them, I either have to bring shoes to drive in, or have to be a passenger. I do love them though!

Instead of just pinning back my hair, I did a little twist-tuck kinda thing to really tuck it out of the way. I also chose my clear glasses from RetroEyeworks, and once again rocked an asymmetrical earring, with the fun one on the shaved side. For this look, I went with a darker eye and a bright pink lip. My necklaces include a vintage 90’s choker I found thrifting, an arrowhead necklace from Express (also sold out, but this is a similar shape and would be great for layering), and just the long part of my Stella & Dot Aria necklace.

Saturday Night: No More Leftovers... Time to Dine Out

This is one of those looks that I think you either love or hate. No doubt, walking into a restaurant in some areas dressed like this would get confused “why is she so dressed up?” looks, but they key to pulling it off is not giving a hoot what people think. I love this look, and would rock the heck out of it at McDonald’s if I had to.

I had actually had a bag for this look, but forgot to grab it when we shot this look. It was just a plain black clutch though, so really there was really nothing groundbreaking missing from the overall look.

Sunday Chic: Break The Rules

It’s been said over and over again that you don’t wear white after Labor Day.  It’s also been said that you should take fashion “rules” and break them, so that’s what I’ve opted to do for the last day of the weekend.

Back to black glasses for this look, which is a little more casual again. It is, after all, Sunday. But just because it’s the last day of the weekend doesn’t mean you can’t dress up just a little. For this look, I opted to break out my white Rock & Republic from Kohl’s jean shorts and layer my faux garter tights underneath them. I think what I like about these tights is that the garter part is on the side, not the front, so they look less… sexy? I dunno. Either way, they work nicely here, creating an over-the-knee look that works nicely with the shorts, offering a little contrast, but not too much that it looks silly.  I decided to wear my thrifted Steve Madden booties with these, largely because they’re easier to pack than the over-the-knee boots I really wanted to wear.  I added a thicker ankle-length athletic sock over the tights (but hidden in the boot nicely) to keep my toes warm.

Both of the tops here are thrifted pieces, and ones I’m sure you’ve seen on me time and time again. But that’s because I really enjoy wearing them. In this case, the flannel covers the sheer back of the graphic tee nicely while also making it a little more fall than spring or summer.  My necklaces (my cheapy long clay, my Stella & Dot Rebel Pendant, and a chevron necklace that got tucked into my shirt and became irrelevant) are mostly long enough that I could add a black scarf to this look without losing them, if it were cooler out.

Sunday Chic: Break The Rules

In the event of too-cold-for-shorts weather, I could work this look with skinny black jeans or I could bring my grey jeans into it and wear those again.  Either pair would work well with these booties, which is part of the reason I bought them.  My backpack, which is kind of hidden, was a gem of a find at Goodwill.  It’s a fab leather backpack that’s so 90’s I absolutely had to have it.  Originally, it was going to be for costume use only, but I love carrying it so much that it’s made its way into my regular rotation.  And it’s a funny thing, because the costume this bag was purchased for actually never really came to fruition. Go figure!

Sunday Chic: Break The Rules

Because I threw my hair up into a ponytail for this look, I opted to go with earrings that matched. Not that I wouldn’t wear mismatched earrings with a pony normally, but I love the way these earrings (older from H&M) look with my Rebel Pendant.  They accent it nicely, without being too matchy-matchy.

And yes, that is a Lazy Girl Mani you see peeking out there. As much as I love painting my nails, on holidays like this where I’m often doing dishes after a big meal, painting all of my nails doesn’t always work. A little pop of gold glitter on one nail works nicely for me.

Sunday Chic: Break The Rules

This look is actually one that, for me, works just as well for hitting up a local vineyard for a wine tasting as it does lounging around the house. I love the ease of the flannel and the tee over the rule-breaking shorts and tights.

So there’s my Thanksgiving Weekend Look Book.

Unfortunately, I have a feeling most of these looks are going to be modified from what’s here, simply based on the weather. They’re calling for slightly-below-average temperatures, so I might have to go with more jeans and leggings instead of skirts and shorts. But that’s ok! This was meant to be a fun look at a variety of outside-the-norm looks for a holiday weekend. I hope you enjoyed it, and maybe get some inspiration for your Thanksgiving looks too (remember, leggings on Thursday mean you can too fit that extra cookie into your food baby!).

Thanks again to Kayleigh Kay Photography!

If you like her work (and I hope you do), go be a fan on Facebook and follow her on Instagram and Twitter.  If you’re in the Chicago area and looking for portraits, baby pictures, event coverage (she does weddings too) or even want something more fashiony like what we did, drop her a line.  You won’t be disappointed!

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