Reader Q | Cute and Comfy Dress For Thanksgiving?



Hi Mamas,

First, I can't thank you enough for all of your style advice – boy, do I sure need it!  Yours is one of the first emails I open each morning.  And even though my husband doesn't always appreciate the shopping-enabling, he does appreciate having a wife who looks a little cuter since discovering your blog!

Anywho, I could really use your help with a Thanksgiving style problem.  Hubs and I trade years with family at the holidays and this year we trek from cold, rainy Seattle to cold, foggy San Francisco to spend the holiday with my clan.  First time on an airplane with both kids – yikes!  So my family always dresses up at holidays and I literally have nothing to wear.  I've been investing in the SAHM wardrobe and have cute jeans, tall boots in brown and black and cozy drapey sweaters, but for actual Thanksgiving, my only few dressy clothes consist of outdated work attire from when I was a CPA pre-kids three years ago and one very tired Banana Republic Factory store dress that I've worn over every Christmas and Thanksgiving for three years as I've gone pregnant, post-partum, repeat.  My sister will disown me if I show up in that thing again.

So I need a dress.  Or else skirt and sweater, but buying just one thing seems less intimidating.  And I have zero shoes beyond my boots, Toms and cute sneaks.  Something that went with tall, flat camel boots would be awesome.  Otherwise, I guess I'm buying shoes, too.  I need something fairly casual and warm since my family members keep the A/C continually cranked at their house.  I'm still nursing, but only a few times during the day, so access is not a must.  I've lost the baby weight, so the dress doesn't have to be major pooch hiding, but on Thanksgiving doesn't everyone need to hide their turkey and pie baby by the end of the day?

Do you have any suggestions for me?

Thank you so much for your help!



Yes.  The answer to your "pie baby" question is a resounding YES.  At least in this household. So J…let's do this thing.  God forbid your sister disown you (I have a sister too, and totally get it).  DISCLAIMER:  I'm assuming that by "dressing up" you mean that everyone is expected to look nice in general.  If your clan is more Grayson Global* than Modern Family, let me know and I'll give you a few ideas offline. 

But for us Modern Family types…here are three cute outfits that would be totally appropriate for all kinds of Thanksgiving festivities…including an extra helping (or two) of pumpkin pie.  

Casual Dress, Glam Jewelry

I love this sweatshirt dress.  Add a chic statement necklace and voila! It's festive.  Let cozy socks with a bit of color peek out over the top of your boots. 


James Perse Raglan Sleeve Sweatshirt Dress, $135 | Spring St Design Group Deco Statement Necklace, $58

Corso Como Rena Boot, $199 | Free People Vintage Over-the-Knee Socks, $20

 Nursing Mamas!  This James Perse neckline *might* stretch (most do)….but if you need more access, try Michael Stars Shine Shirred dress in Cinnamon.  Swap the necklace for this cool art deco cuff bracelet, and try the socks in the darker navy or even black.


Pretty Tunic, Leather Leggings, Fur Vest

Really.  This is such a glam way to dress up.  And so stretchy!  Between the cut of the top and the faux-fur, that pie baby will be covered, and you'll be warm. 

 ASOS Warehouse Spot Print Tunic, $74 (or this dress, for more bum coverage) | Banana Republic Faux Fur Vest, $125 | Topshop Faux-leather legging just sold out…but Target has these for $30! | Corso Como Rena Boot, $199


A Mod Little Shift Dress

Shift dresses are funny things.  They skim the curves, yet manage to hide little food babies.  Plus, a girl in a shift always looks put-together…making them pretty. darn. perfect. for Thanksgiving.  

Make sure the length is on the shorter side.  This keeps the vibe mod, especially with tall boots.  Add opaque tights and a turtleneck if you are very cold. (Or swap the turtleneck for a slim-cut chambray shirt.  All the hipsters do it.)


Madewell Photoflower Shift Dress, $150 | J.Crew Tissue Turtleneck, $40 | Corso Como Rena Boot, $199


Nursing mama?  Try this shift dress instead from Anthropologie (Drool. Worthy.), or this lower cost one from the Gap.

I hope this helps, J!  Thanks for writing in!



ps.  How are my price points, Mamas?  I usually try to include a wider range, but I haven't been impressed with our low-cost retailers lately.  (Old Navy had a shockingly good fall, but are now sold out of all the good stuff.)  So I tried to focus on pieces that could be worn again&again&again…instead of just some cheap holiday dress.  Thoughts?  Was this a hit or miss?

*I'm a huge Revenge fan. 


  1. Total side topic, but I just got sucked in to Revenge on Netflix. So good! How did I miss it earlier? I just finished season 1… luckily ABC has season 2 on their website.
    And, I love these outfit ideas. 🙂

  2. I love 1 and 3! My family is the Fockers, and my in laws are the same as the movie. I would love a bit more sophisticated option for them 😉

  3. Hmm, cute options but I need a bit more sophisticated too. We do T-Day with the in-laws. It’s at the country club. My MIL is usually in Chanel. My budget is more Tarjay.
    My plan was an old stretched out banana republic black knit dress that I also wore through pre-pregs, pregs, and post partum holidays already.
    After reading this blog post I’m feeling a little guilty about that choice.
    May I request a fancier follow up to this post? pretty please!

  4. Shopping. Enabler. I just bought that blue gap dress for Turkey day and my little sister’s birthday party. That puts the cost per wear at $25 right off the bat!

  5. My T day will be Meet the Fokkers, too- but the crazy FL ones not the stuffy LI ones! After being pregnant the past two, this puts me in the mood to dress up anyway, though. I have a dress quite similar to the Michael Stars one but DAMN! that James Perse is going to haunt my dreams…. Thanks for the styling inspiration!

  6. I would love a few items that are a little dressier, and also at lower price points. I know I’m asking a lot, but that’s where I am at this stage of life! I would love it if you did this for Christmas dresses as well!

  7. Price points are a little high for my tastes…but that’s because I don’t wear dresses. Like ever. So every dress I buy has to be calculated PPW where the W<5. Do love that first dress. For some reason, I just can't warm up to shirt dresses.

  8. Jen-I found this dress: dress in teal on clearance at my local Target and bought it because it was so cheap and I liked the color, and I totally love it!! The deep v and the shape in general means it’s easy to pair with a cami and pull aside the dress and pull up the cami to nurse if needed, and the high waist and extra fabric from the twist means it still fits nicely when pregnant. And it looks cute not pregnant or nursing too (and again, the high waist and extra fabric from the twist kinda hides any mid-section bulk, lol.) Mine is long enough on me that I can wear it without leggings, but it is so cold here I usually wear leggings and cozy boots with it. I’ve worn it with heels and hose and it looks good that way too!
    Looks like all they have left is black and gray, but either would be cute with a cranberry colored cami for a little fall color, plus you can never go wrong with a little black dress!

  9. PS I’m not sure what the mesh lining they are talking about. In the picture it looks exactly like the one I have, which includes no mesh lining. If it is one of those annoying built in faux camis that is supposed to cover your cleavage, I hate those, but you can probably just cut it out pretty easily. Or maybe it would work for you (I am quite busty and need much more coverage than those ever provide, but then can’t wear a cami when there is already the appearance of one, you know?)

  10. Love this, the first outfit is my favorite, looks so comfy and cute. The price points are a bit high, but all of these pieces could be worn again and again, so quality triumphs over quantity again!
    Can I request a maternity version of this!? I’m five months pregnant with my second, and have nothing cute to wear for the holidays! Would be great to see a range of dressiness. I have a fancy work party for my husband’s company, and more casual gatherings with family. OH, and nothing from the first time around fits 🙁 Starting from scratch here…. Any advice for maternity building blocks that are decent quality and not crazy expensive (I’m obsessed with the Hatch line, but I just can’t justify $250 right now for a maternity dress!)
    Thanks and love your blog!

  11. I have to say…I really, REALLY like the sweatshirt dress. With the holidays coming up and an unexpected dip in household funds, I wonder if I can find a less expensive version…I am usually all about the quality, but IDK how many seasons I would wear that…
    Guess I am on the hunt now…LOL!

  12. I’m considering this shirt for Thanksgiving.!/photo.php?fbid=10151277331315939&set=a.165668140938.120124.154628175938&type=3&theater
    Pair it with a black cami and you could nurse if you need to with easy access. I wore it to work with a teal pencil skirt I picked up at Nordstrom’s anniversary sale, but IDK if that would work for Thanksgiving or not.
    And I LOVE Revenge – I’ve watched it from the start! I actually watched two back to back last night because I had to catch up on some “Mommy television” after the kids went to sleep!

  13. The price points are pretty high for me but I’m fairly new to this blog (LOVE it so far – so practical and spot on with my age!) and still trying to convince myself that it’s worth it to invest in a few quality outfits that I love. I’m more the $6 shirt from the clearance rack at Target type and would consider the Gap option a splurge.
    I’m still going through the archives but if you haven’t already addressed it, I would love to see a post on building a long term wardrobe when your weight is ALWAYS fluctuating (even with no babies involved). I’m a 3/4/5 – I know I’m lucky and most wouldn’t consider that “fat” but 5-8 lbs makes all the difference in my tummy and thigh area and can be the difference between whether jeans fit perfectly or are uncomfortably tight and causing an unattrative muffin top and whether tops are flattering or pudge revealing. (A very small chest means I tend to disappear in tops that are too loose – or maybe that’s a drape issue from buying super cheap shirts). At the $40-$75 each range (I’m not quite ready to consider $75-$125), I can buy one or two pieces per month, which means by the time I’ve built up a couple outfits the first purchases probably won’t fit, at least not the same way. Do I build two wardrobes and rotate them as my weight changes?

  14. I love good television in the winter and Revenge is at the top of my list. This made me laugh because my husband, who I believe secretly reads your blog, has been nagging me to wear more leggings. I can’t help but think if I put on those leather leggings, I might end up with more than just a pie baby from this Thanksgiving. Thanks for the awesome blog!

  15. I *wish* we dressed like the Graysons. I drool over Emily’s purses every episode. I adore that blue Anthro dress, b/c it’s perfect for nursing, but doesn’t look like a nursing dress.
    That James Perse one, actually looks like it would be appropriate for winter and fall. Just not so nursing friendly. Nice price points. I did notice you were a little more budget reasonable this time. Thanks.

  16. Perfect post. I was just realizing that I don’t have anything to wear but the same sorry outfit I’ve worn for the last four years. Style was spot-on for our family’s gathering.
    Prices were fine for me. I usually have one or two of these outfits going at a few years, so the price per wear is good (the BR wrap dress that I’m retiring was ~$80 four years ago, for reference), and the outfits built off basics that I would already have, so I’m looking at just 1-2 pieces.

  17. I like the outfits for a more casual family but for those whose family is a little more traditional and not quite as trendy (if I showed up with leather leggings and a fur vest they would think I was trying to be 18 again!), one option I suggest is to find a stretchy (comfortable) wool-blend skirt – hopefully a cheaper version of this{keyword} and pair it with a looser cowl neck sweater and tights and the camel boots.

  18. I love the first outfit for me and maybe even the second one- if the tunic top was different- I worry that the tie will hit me in an awkward spot. I am off to purchase the James Perse dress today- so thank you for enabling my shopping habit- well, for starting it. For so long I was stuck in a rut and this blog and your style sense provide much needed inspiration.
    On that note- I live in Boston. It is cold here- can I wear tights AND those cute socks over them to peek out of the boots? Or is that a fashion don’t?!?!?

  19. Love these picks, especially the first one…and might I add, I LOVE that you include options for nursing mamas. So great! I’m due any time with my 3rd and that Gap shift dress would be so cute for the holidays!

  20. I actually found a sweatshirt dress at Target. Don’t know if they still have them but, it is their Merona brand and I think it was $24.99. I’m preggo and I’ve been wearing it but, it’s not maternity. It is very cute and comfy and I wear it with boots and leggings, and knee socks. 🙂

  21. I love these options and the price points are right on. I bought the JP dress and think that it would also look cute with tights and ankle moto booties for date night, or leggings-scarf-sneaks for play date. CPW ends up being nominal.

  22. Awesome outfit ideas (and underpinning tips!) Please do keep the higher price points in the mix too! I love a bargain as much as the next girl, but I don’t consider it a bargain until it’s worn well several times, endured a few washings, and holds up over the long run. For sure c.p.w is important and I’d add to that t.i.p.w. as well – time investment per wear. I’d rather buy a single item at 3x the price if it will look fabulous over the long haul than have to shop for (and spend on) 3 generations of similar item over the same time period. There’s also something to be said in terms of good global citizenship for buying less stuff, and repairing/retaining/reusing the stuff one does buy. My favorite black ankle boots were a MAJOR splurge up front, but headed into a fourth winter with a fresh coat of shoe polish and some new heel caps they continue to drop in cpw/tipw – and I still feel like a total minx every time I stroll down the sidewalk in them. (Even if I’m strolling with banana smeared on my shoulder and a portable toilet seat in my purse!)

  23. Thanks as ever. Love ANMJ. I’ve coveted the JP dress for awhile (briefly borrowed one from a friend when I was pregnant with my girls). And…I ordered it. If it looks cute, maybe, just maybe, I will report back. I’m still working on the last 15 lbs.
    The price points are perfect, thanks!

  24. Loved and bought the first outfit (dress and necklace). Would love to see a post with this dress styled different ways – right now I’m trying to work in a plaid for xmas somehow….
    Also, I live in Baltimore and was glad to see the post on your visit! Would love to meet up when you guys come back!

  25. I would never, ever spend $150 on a dress at my current stage in life. Though I love the last dress. I think more expensive options are fine as long as it’s $150 not $450. I usually look at the general idea of how you pair things together rather than I need to buy that specific item. I usually try to re-style what I already have.
    Also, those Target faux leather leggings are now $15.

Leave a Reply