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Dressing Up for the Holidays (Plus, a J.Crew Discount)

Our Family Dinner Ritual

Nine-year-old Toby has never met a ritual he doesn’t love, so he came up with a great idea for the winter…

Our Family Dinner Ritual

He suggested that once a month, we all dress up and go to dinner. When he first suggested it, I figured he wanted to go to super fancy places, but he proposed the local Indian place and our neighborhood diner. This month, we went to Rucola, a low-key Italian spot. The boys ordered Shirley Temples, and they always love the bread basket. To make it feel extra special, we dressed up in holiday outfits from J.Crew.

Our Family Dinner Ritual

Toby has always been into the idea of suits. (For his fourth birthday, he asked for a blazer.) Here, he’s wearing the Ludlow suit jacket and pants, paired with this button-down. All of the pieces have a hint of stretch, for extra comfort. And he’s really into the velvet slippers, which are reserved for the fanciest of occasions. (These are also cute.)

Our Family Dinner Ritual

Meanwhile, when it comes to dressing up, Anton goes with the flow. He mostly wants comfy pants and sneakers. Anton wore his Fair Isle half-zip, which he has pulled on many times since. (He likes that it has dogs.)

I’ve spotted slip skirts on other women around town, and this burgundy one is such a nice winter color. I paired it with a V-neck sweater I’ve worn approximately one thousand times. I like that it looks equally good dressed up or down — I’ve even worn mine with joggers! And these suede heels are comfy enough to walk around in and pull everything together.

Our Family Dinner Ritual

When it comes to dress-up clothes, J.Crew always gets it right. The fit is great and the little details make every occasion feel special. (How pretty is this look?) Plus, they’re the kind of pieces that work perfectly for weddings, family parties, celebratory dinners, and all those special life moments.

Do you have any holiday rituals or traditions? I’d love to hear…

Bonus for all readers: J.Crew is offering Cup of Jo readers 15% off (stackable on top of other sales) using code CUPOFJO. (I have my eye on this.) Good through December 18th. Thank you so much!

(Photos by Christine Han for Cup of Jo. This post is sponsored by J.Crew, a brand our family has worn for years. Thank you for supporting the brands that help keep Cup of Jo running.)

  1. Thank you for the code. I have just purchased two long sleeve cashmere sweaters at 50% off (today’s promo) & used your code as well. I’ll be doing my happy dance the whole day today. :)
    Also to other readers, JCrew do collaborate with Sustainable Fibre Alliance (SFA), an international nonprofit working to create a more sustainable cashmere supply chain i.e supporting its efforts to ensure animal welfare, advocate for herding communities, restoring grasslands and reducing cashmere’s environmental footprint. More info at sustainablefibre.org.
    Joanna, please don’t stop doing this. And you have two very handsome young men there.

  2. Adreanna says...

    Stacked the coupon code with J.Crew’s 50% off sale today and got a pencil skirt I’ve been needing to replace for such a long time and two new long sleeve shirts for $51.00!

    Thank you for the code, and these are some great pictures of you and your boys.

    • Joanna Goddard says...

      thank you, and i’m so glad!

  3. Tracy says...

    I don’t think Toby is capable of taking a bad picture. Such a handsome little guy (they both are!)

    • Joanna Goddard says...

      aww, thank you!

  4. carole says...

    Such a beautiful family! I love these posts about real life, these special moments that make up our life. What a beautiful tradition you are creating and memories to last a life time :) XO

  5. Allison says...

    Is the promo code only for US? Doesn’t work for me (canada).

  6. peach goff says...

    oh my gosh… i love that he asked for a blazer for his birthday. my 3rd son who is now 25 asked for a blazer when he was probably 2nd grade…we bought it at j.c. penneys

  7. Danielle says...

    What gorgeous photos of the Brothers! Toby definitely strikes me as a velvet slipper kind of future adult. I feel like he’d be super into pocket squares

  8. Gabi M says...

    One year ago I swore I thought my proposal was happening when my then boyfriend told me we were going to dress nice and go to a nice dinner. Imagine my dissapointment when it didn’t happen. Don’t worry! He proposed two weeks later on my bithday and we are now married! However, we decided to keep this fancy dinner around the holidays a favorite tradition. To me it is special because it is a reminder that during the holidays, we get so focused on expectations and craziness and this dinner is a time to come together and be present. Can’t wait to do this with our family one day and laugh about how this tradition even started :)

  9. JennyH says...

    I loved the Traxedo idea that Primary featured last month with the black track suit, white button down, and black bow-tie. Both comfortable and adorable, for young ones. Maybe a cute idea for a New Years Eve get together.

  10. A different Nora, actually says...

    second this. COJ, you now are big enough to get to PICK which advertisers and partners you work with! that you would choose JCrew is disappointing.

    • A different Nora, actually says...

      This is in regard to Jcrew’s (lack of) sustainability systems and reporting

  11. Ceridwen says...

    Such a lovely idea! Toby is really the romantic.

  12. Nora says...

    Very cute pictures, but I’m disappointed to see Cup of Jo running such a big splashy ad with J.Crew.

    Green America has released a Scorecard of Environmental and Social Practices of Major US Apparel Companies, and J.Crew is SECOND TO LAST, only above the (rightfully) now defunct Forever 21. That is because J. Crew has an almost total “lack of transparency in its sustainability and labor polices — if it has policies on those issues, it’s keeping them a secret.” (Green America)

    You can check their scorecard out at:  https://www.greenamerica.org/2019-toxic-textiles-scorecard

    Given that the fashion industry is a major source of GHG emissions, depletes our soil and water supply, uses toxic pesticides and chemicals, and exploits some of the poorest and most vulnerable workers in the world . . . don’t we, in the global north, who have the privilege to be able to afford such things as a $220 blazer for a child, have the responsibility to demand better of the companies who sell them? 

    • Rose says...

      Well said!

    • M says...

      Thank you for sharing this, Nora. My thoughts exactly. And to answer your question, yes, we (who have $220 to spare for a child’s blazer) do have that responsibility. Platforms with this type of following have that responsibility and should be pushing its readers towards more eco-friendly and thoughtful consumerism whenever possible. J.Crew does not fit the bill.

    • Shannon McGuigan says...

      Hear hear!

    • Ashley says...

      I really couldn’t agree more.

      Yes your children are darling, and it’s lovely to watch them grow up, and they’re also stewards of this fragile planet as much as we are.

      I don’t want to just post negativity here, but we have so much power with our choices. We have to have more power with our choices.

      Unfortunately, I’m becoming less interested in this blog given all the posts pushing consumerism. The community is wonderful, and I understand you run a business, but for me it’s coming down to a moral issue I’m becoming more aware of.

      How could you evolve Cup of Jo so it’s something highly reflective of these changing times we’re facing? We know you care.

      You have a community of people that also seem to care. How can we help you evolve what you’ve built so you can pay your bills and do the great work you do AND do even better for the planet? Let us help you.

      In the strong words of my own mentor, make it better.

      It’s a statement I force myself to think about everyday when I’m faced with the reality (and fear) of our quickly changing planet- make it better.

    • Luna says...

      Agree. CoJ, we love you, but use your platform for the good!

    • Elizabeth says...

      Agree with what was said here!
      It’s 2019 and if TIME’s Person of the Year Choice is any indication, when females take the lead in speaking truth to power change begins. Our planet is on fire. J.Crew is profit over the planet. We all must wake up and look at our consumer habits. Boycott these labels and support sustainable fashion and second-hand. Cup of Jo’s platform could grow, expand AND do good, by evolving away from fast fashion and pointing in a new direction. The one Greta’s looking out at in that TIME cover.

      “the brand has few environmental practices set in place in its production line. It doesn’t use eco-friendly materials, provides no evidence that it has a greenhouse gas emissions reduction target, or that it is taking adequate steps to minimise or eliminate hazardous chemicals. It has no policies or initiatives on water usage and wastewater management in supply chain and doesn’t specifically states how it minimises non-textile waste. What’s more it doesn’t have adequate policies and initiatives for resources management and disposal. A pretty dirty result from a brand with such a clean image.” I’ll say.

      And If anyone really wants some J Crew, do the responsible thing and buy it on ThredUP. They have a ton!

    • Kylee says...

      J Crew (Crew cuts, specifically) was a major sponsor for a runway show for children with cancer that my daughter was part of. So they’re not entirely heartless, lack of transparency aside.
      https://www.runwayheroes.com/events

  13. oh my gosh. Can you and your family be more beautiful? So lovely!

  14. mollcoll says...

    Love this partnership and post. Jcrew never fails and they boys are getting so grown up <3

  15. Suzie says...

    Adorable! What a beautiful family. How special to have these pictures. Happy holidays!

  16. Cynthia says...

    Such a sweet family picture! It’s fun to dress up and go out for a meal.

  17. Cynthia says...

    Such a sweet family picture! You all look so nice dressed up, and I think it’s a great idea to dress up and go out for a meal.

  18. Sarah Clark says...

    Doesn’t look like the promo code is working?

  19. celeste says...

    You all look terrific and I love the haircuts! My son’s fashion leans towards Toby’s taste – he wore a jacket to his Christmas concert and finds sweaters itchy. I lamented this to my husband and he shrugged and said, “I hated sweaters too when I was a kid.” What cute doggos though!

  20. Jackie says...

    You are gorgeous Joanna! Fun to see a sweet date for your family. I’m sure you’ll love the images for years to come, what a gift.

  21. Lindsey says...

    This is precious, Joanna. You are the only person on the internet whose sponsored content I will entertain. You have a gift for smoothing over the connections between real life and business that I truly admire.

    • Joanna Goddard says...

      that’s so sweet, thank you so much, lindsey xo

    • Olga says...

      I agree. I really don’t mind your sponsored content at all.
      xox

    • Elise says...

      I totally agree! I read all the sponsored content because it is entertaining AND transparent. Plus it’s generally relevant to my life and shopping habits!

  22. Lynn says...

    Oh boo! WEDNESDAY is already over. I clicked through but it was Too Late.

    • Maureen says...

      Hi Lynn! Breaking news, J.Crew is offering Cup of Jo readers 15% off (stackable on top of other sales) using code CUPOFJO. Happy shopping!

  23. Mouse says...

    I love the idea of winter rituals, and Toby is The Man, fashion-wise. (Still want to marry Anton though) I wonder if another ritual they might enjoy would be some kind of live show, like the Nutcracker or Handel’s Messiah or some American version of English panto? There could be some serious dress-up for concert-going…..:)

  24. Sarah says...

    Aww, this post made me miss J. Crew! I live in Norway where we don’t have the shops and we have exorbitant tolls so I can’t really order their stuff online either.
    You and the little guys look so cute. I love the white sweater.

  25. Gaby says...

    Every year to pick out our tree, I put on a coat and red gloves, and like to have a warm beverage from Starbucks – white hot chocolate! I finally gave up on that tradition bc I live in the deep south and it’s not cold. 😂

  26. Lynn-Holly Wielenga says...

    Ahh I love j.crew (especially when they have a sale on their sale…) and I love this post! I just had a baby boy 6 weeks ago and this makes me so excited for future rituals and traditions with him.

  27. Connor Novy says...

    I just took of a pair of satin pumps with GLITTER SOLES from j crew that I wore to my company’s holiday party. They were perfect. I highly recommend. Did feel like I had diamonds on the soles of my shoes all night.

    • Em says...

      Beautiful :-)

  28. What a lovely post. I’m always inspired by Toby’s looks and that burgundy slip skirt is so gorgeous and looks comfortable and chic.

  29. Ally says...

    Aw, Toby’s looking like a classy gent!

  30. Kate says...

    You are such a beauty, and you all look so happy. Good work!

  31. Jamie Thiel says...

    Toby out of black leggings and into a suit! Who knew? He is one adorably handsome little man. They appear to be very opposite and yet quite complementary of one another, lucky brothers indeed. Not to mention mom and dad.

    • I love this idea and need to start doing it with my daughter for 2020! I’m a single mom, entrepreneur who works from home and a yoga and dance teacher. I’m a card carrying member of the yoga pants nation and this would force me to put on at least jeans and a blouse!

  32. Nicole says...

    Oh my, this is so sweet. I have two little boys (2.5 yrs and 10 months), and your posts fill me with such happy anticipation for what they will be like. While I am already nostalgic for their baby days, I just can’t wait to see who they become!

  33. CS says...

    Aww! The boys look so handsome! Lovely new tradition.

  34. Jessie says...

    Yes! We do a very touristy DC tradition. We go to Old Ebbitt Grill for lunch and then go and see the Tree. Once our daughters are a little older we will also include seeing The Nutcracker.

  35. Ruth says...

    Can I just say “thank you” for featuring a winter outfit WITH tights? It drives me crazy that all of the websites and catalogues feature bare-legged women. They look so chic, but all I can think is “I’d be freezing in that!”

    • Em says...

      Amen sistah. I think this all the time, and end up feeling confused and frumpy when I put on tights even though it’s TOTALLY APPROPRIATE. Also, super super cute Jo

    • Bobby says...

      When you feel frumpy, just console yourself with the fact that the Duchess of Cambridge always wears tights!

    • Libby says...

      I adore wearing tights in the winter time, and they look so nice. Once of my very conservative finance clients actually has a dress code rule about how women can’t wear tights! Can you imagine such a ridiculous rule, and in the middle of winter? When I visit them, I have to be sure that I follow their dress code, which means wearing flesh-colored pantyhose.

    • C. says...

      Yes, agreed. And don’t get me started on winter outfits that include thin sleeveless tops or tanks with spaghetti straps.

    • Cynthia says...

      I always wear tights in the winter, and I have gray, tan, and navy as well as classic black.

  36. Abesha1 says...

    So cute.
    This felt to me like a sponsored post that was really genuine, Joanna– It connects so many things that are true to you as a person.

    • Mel says...

      I had the SAME thought. Such a good sponsored post, actually made me smile, actually made me come up with ideas for my family and actually made me click on over to peruse the store. Well done CoJ, as walsy

  37. Erin says...

    That’s awesome that your boys are civilized at quiet restaurants, we aren’t quite there yet! Your boys are adorable. Wishing you a magical Christmas.

  38. ana says...

    Beautiful Toby looks so grown up!
    Happy Christmas x

    • Trish says...

      I Remember that birthday blazer post 🤩 just looked back at it and am wondering how long Dun Dun hung around ? My 4 year old niece has a best imaginary buddy called Ciara who is 5 and drives her own convertible car . She also gets to stay up super late with the adults and eat lots of chocolate . They met in a park apparently 🥰
      My brother had a imaginary pal called Dick ! Dick did all the naughty stuff at home and “Dick did it” was his regular answer to get himself out of trouble . X

    • agnes says...

      Hi Trish, I had an imaginary friend for a loooong time, maybe until I was 13. I have to admit that it reappears sometimes (I’m 47); it’s a beautiful black horse. My son had an imaginary friend until he was 6; he would even draw him (Max), with the rest of the family members! Psychologists say it’s very positive, I’m relieved ;-)

  39. Natalia says...

    Ooomigoodness son goals! Those two are so adorable (and fashionable!) and you wear your love for them with such warmth. Just the sweetest photos of the three of you. I don’t have kids yet but I’m so worried I’ll end up with a couple of meatheads like my husband’s two brothers, ha! My husband is a lot more, um … how shall I put it … sophisticated. I hope he passes his traits along but I always tell him I want a gay son or two and seeing yours gives me hope :)

  40. Erin Baird says...

    OMG that one of Anton with the cup!! He looks so tiny and so grown up at the same time!

  41. Emily says...

    Just the other day, my 2.5 year old asked if we were going to dress up for Christmas. I said, “Yes, definitely. We’ll wear really nice clothes!” And he replied, “I’m going to dress up like a hammerhead shark.” That’s when I realized dressing up can have different meanings for different people!

    • jrg says...

      omg this is adorable

    • Laura says...

      so sweet!

    • Sarah says...

      Hahaha I had the same convo with my 2.5 year old! When Halloween was over she asked “What are you going to be for Christmas?” When I explained that costumes are just for Halloween and thought for a moment then said: “I will be a blanket.” LOL.

    • Ez says...

      Hahaha, that reminds me of one time when I asked my 6-year-old if she wanted to put on a mask with me. We were jet lagged, so she was up way past bedtime. So we put on mud packs and sat down to watch tv, and she was looking a bit disconcerted. Then I was like – oh! Did you think I meant like a dress-up mask?? Yep. She did. The best thing about it is that she thought that’s something I would do! Wait until after her bedtime, then put on a dress-mask 😄

  42. Sadie says...

    You three look perfect. xo

  43. amy says...

    Adorable! Has anyone else been really disappointed with J Crew quality lately?

    • Sandra says...

      Yup. I keep telling myself I won’t buy anything else from them until they get it together, then I cave, buy something, and am reminded why I shouldn’t have.

      They knew how to make great stuff in the 1980s and 90s and even early 2000s, so what happened? Almost every sweater I’ve gotten there lately has pilled (other than the 1988 cotton rollneck, which is great). Bring back your “Friends”-era quality, J. Crew!

    • Charlotte says...

      I have been, for the last few years! I worked there briefly in college many moons ago and although the styles have always been great I’ve found the quality to be totally hit or miss, even then. It’s a shame, because I’m absolutely willing to pony up the money for something that will last. You can’t equate something that is pricey with something that is quality anymore, unfortunately.

    • Margoulette says...

      Yes, quality is inconsistent, so is the sizing, but their customer service is pretty great!

    • Milou says...

      I have loved/worn J Crew since high school. I remember in college (early 90’s) when the J Crew catalogue came, every girl at my small women’s college let out a small yelp of joy. Even my first suit was purchased there!

      Sadly, I agree with the above – the quality is not what it once was. I feel like many of their pieces still look cute online, but can appear cheap-looking in person.

    • MJ says...

      I have strayed away from JCrew over the past 5 years because of prices and quality.

      I was cleaning out closets the other day and found my first J Crew purchase from college – a fleece 1/4 zip pullover jacket, circa 1994. It’s still in perfect condition – so soft and warm! My 12 yo and I are sharing it!

    • Beth says...

      No doubt that J. Crew has great styling and designs, but the quality is truly bad. I started shopping there around 1995 when the pieces were rock solid and finally quit around 2012. I read somewhere that the worst value in clothing are the prestige fast fashion brands, which fits J. Crew to a T. There are much better options out there! I understand the emotional/nostalgic appeal of J. Crew but they are not keeping up with the times and I believe their days are numbered…

      I wish Cup of Jo would take a more progressive/conscious approach to the brands they feature, but also understand that they also have to make money.

    • Katie says...

      Beth – what brands would you like to see featured? Just curious!

    • AN says...

      Agree. I bought two colors of one of the sweaters featured here for a recent trip to Europe and it literally pilled the first time I wore the black one. I never even put on the other color, thank goodness they let me return both. I’m so happy to pay more for quality that lasts…

  44. Laura J says...

    Goodness, Toby sounds like my son. He used to wear a button down shirt with khaki pants to preschool. The teachers would look at me and say, “You know we are painting today…” Yes but this is how he likes to dress. I’m okay with paint stains. It wasn’t quite as pronounced later but as an adult, he has a much better sense of fashion than I ever had and wears it very well. He helped me at Thanksgiving with a skirt I was struggling to find the right top to go with it. He figured it out and I’m good to go. ; )

    • Joanna Goddard says...

      i love hearing that, laura!

  45. becky says...

    Aww Anton I love dogs on my clothes too!
    I love that they both know their own style at such a young age!

  46. Emily says...

    Oh, they are so sweet!! I adore how Toby loves dressing up. What a lovely post.

  47. Ruth says...

    Toby really should have his own YouTube channel; he is a charmer (as is Anton). Love the suit, the rituals, the general sunny vibe of these kids.

    • Joanna Goddard says...

      haha he is a character for sure! thank you for your sweet note. xo

  48. Andrea says...

    freshly pregnant with my second and this post is making me think two litte boys would be fun to hang out with (despite all the “I bet you hope it’s a girl!” talk) :)

    • Joanna Goddard says...

      oh yes, it’s wonderful to have two boys! they are so sweet, vulnerable, loving, funny… :) and congratulations!!

    • Tilly says...

      This used to really rile me when I was pregnant the second time, knowing that we were expecting a second boy, a fact that we didn’t share before the birth. Almost everyone seemed to think that a boy would be the dud prize and particularly a second boy! Horror of horrors. It’s a very strange attitude. But, like Joanna, I can honestly say that I love having two boys and they love having each other. It’s all good! Congratulations!!

  49. m says...

    No need to publish but just a gentle FYI that you might want to proof-read, you seem to be missing some links to the items and some words also. Not trying to snark, love the blog x

    • Joanna Goddard says...

      oh yes, it’s because of the tracking codes on the links — they’re deleted by ad blockers. we’re fixing now, thank you!

    • Daria says...

      Oh yes, I had the same thing on Firefox with my Adblock on!

  50. Claudia says...

    Whoops! Ladies, am I missing some links and words or does the text seem to be a draft version? Anyway, Toby always has the best ideas and dressing up for a dinner is always a fun thing to do! You guys look gorgeous and that dark red slip skirt looks so chic!

    • Joanna Goddard says...

      we’re on it! thank you! xoxo

    • Mandy says...

      You all look lovely and what a good idea to brighten winter xx

    • Bea6 says...

      Thank you for the code, but it doesn’t apply to the lovely skirt you’re wearing since it’s excluded from promos of all sorts. Unless someone found a different way to apply it?

  51. Kim says...

    They are so dapper! I love this tradition.

  52. Stacey says...

    If anyone else is using uBlock, it blocks the product links. I was reading “Here, he’s wearing the and , paired with . ”

    To fix, you can access Filter lists and check “Ignore generic cosmetic filters”, which worked for me.

    • Claudia says...

      Thank you for the heads-up, Stacey! Disabled the adblock and can now enjoy the whole article!

  53. Lauren C says...

    Oh my goodness, these cute little gentlemen!