5 Fall Outfits for Little Boys

Happy Monday, friends!

I hope your week is off to a great start! 

I don’t know about you, but October is one of my two favorite months out of the year.  From the cooler weather, the changing of the leaves, fall festivities, and pumpkin spiced everything, I get giddy with excitement! All that to say, we have been taking full advantage of what the fall season has to offer and trying to really soak it up.  

One of our favorite fall traditions is visiting a pumpkin patch and I am happy to report that we didn’t waste any time getting this checked off from our to do list.  We went at the beginning of October to Dell’Osso Family Farm and it didn’t disappoint.  In case you missed it, I posted a little photo dump on Instagram last week.   

Speaking of traditions, I am a sucker for Halloween! I wasn’t a particularly big Halloween person growing up, but now I am obsessed! The cute spooky decorations, endless treats and of course, the Mommy and Me dressing up – what’s there not to love? Though the real question is, do you or your kids know what you are wearing yet? If you need ideas, I am sharing some of my son’s past costumes on IG this Thursday so, make sure to check back in! 

In the meantime, let’s get to today’s post… 

As much as I love shopping for myself, I honestly have so much more fun finding and buying more things for my little guy.  I am always on the lookout for unique and adorable pieces for him that would easily mix and match with what he already has.  Last month, I took advantage of some sales and did a little online shopping to update his closet.  I had an Amazon GC and some Super Cash burning a hole in my pocket and found some great pieces.  That said, my little guy and I put together five head-to-toe looks to share with you all today.  These outfits are perfect for school, running errands, family photos and so much more.  In fact, all these pieces are perfect for fall, but they can also be mixed into your child’s winter and spring wardrobe too!

Outfit #1

Fall Outfit Sweater Vest Photo

Vest | Shirt | Pants | Shoes | Sunglasses

Outfit #2

Fall Style for Little Boys Jogger Set Photo

Hoodie | Joggers | Shirt | Shoes | Sunglasses

Outfit #3

Fall Style Colorful Striped Sweater Photo

Sweater | Pants | Shoes | Beanie | Sunglasses

Outfit #4

Fall Outfit Dinosaur Button Down Shirt Photo

Dinosaur Shirt | Pants | Shoes | Hat | Sunglasses

Outfit #5

Fall Outfit for Little Boys Red Flannel Shirt with Overalls Photo

Red Plaid Shirt | T-shirt | Overalls | Rain Boots | Sunglasses

Well that’s about it for today.  I hope this gave you all some fun outfit ideas for the upcoming season! Which outfit is your favorite?

*Disclosure: This post contains affiliate links.  If you click through and make a purchase, I may receive a commission (at no additional cost to you).  

44 COMMENTS

  1. Melanie Edjourian | 15th Mar 22

    Your son looks adorable. What a lovely selection of images. The clothing looks so cute on him. It would be ideal for my son too. He seems to be of a similar age.

  2. Gentry | 14th Nov 21

    Oh my goodness, your little man looks so stylish and adorable!

  3. Jessica A Jannenga | 8th Nov 21

    Hi Maureen!
    Your son is adorable and so fashionable! He seems to really enjoy fashion! Love the leopard vest and loafers, and the darby hat is so stylin! I enjoyed seeing all his little outfits! You must have fun buying them:-)
    I love October too, and Fall is my favorite season, has been since I was a kid.
    thanks for linking!
    jess xx
    http://www.elegantlydressedandstylish.com

  4. Rach | 5th Nov 21

    Aww your son’s outfits are so cute! I never thought it would be so fun to dress boys but now that I have a son, it’s so fun and there’s definitely a lot more cute options than I expected. We unfortunately didn’t have any time to do any Fall activities, but hopefully next year we can!

    http://www.rdsobsessions.com

  5. Carrie @ Curly Crafty Mom | 5th Nov 21

    What a cutie he is in these clothes! I love the leopard vest outfit and the red boots with the overalls in the last outfit!

    Carrie
    curlycraftymom.com

  6. Biana | 2nd Nov 21

    these are all too cute! Love them all especially number 3

  7. Rosie | 2nd Nov 21

    Oh all are so cute! Love each outfit!

  8. Cristina | 1st Nov 21

    Oh my, what a fashionable cutie! I love all the outfits. And by the way, I wasn’t a big fan of Halloween either until I became a mom.

  9. Abby | 1st Nov 21

    All the outfits are absolutely adorable. I especially like the #5 with the overalls!

  10. Laura | 1st Nov 21

    These are all absolutely adorable!

  11. Rachel | 1st Nov 21

    These outfits are all so cute! I especially like outfit #3; I love stripes! Thanks for sharing!

  12. Anita | 1st Nov 21

    These outfits are just as cute as they can be! And the sunglasses and hats add even more. Adorable!

  13. Mica | 28th Oct 21

    This looks like a fun photoshoot! Your son got some really cute outfits, love the third one with the striped jumper! 🙂

    Hope that you are having a great week 🙂

  14. Julia Rees | 28th Oct 21

    All these outfits are so cute, and your son is a great model!
    Julia x
    https://www.thevelvetrunway.com/

  15. Kate | 27th Oct 21

    Too cute! Love all of little man’s looks 🙂

  16. Marisa Cavaleiro | 26th Oct 21

    Wow your son is very cool! I love all the outfits!
    In my country Halloween is not a tradition, I’m glad you like it!
    xoxo

    marisasclosetblog.com

  17. Ashley | 26th Oct 21

    Your little dude has so much style! I love these fall ‘fits!

    -Ashley
    Le Stylo Rouge

  18. Pooja Sharma | 26th Oct 21

    these are great outfits! Every outfit would suit my son and I would love to add these to his closet especially the red shirt

  19. Nina | 25th Oct 21

    So cute! Love all the outfits.
    -Nina
    http://www.stylingwithnina.com/2021/10/sweater-season.html

  20. Theresa Boedeker | 25th Oct 21

    Such cute outfits. You have proved little boy clothes can be adorable and creative.

  21. Clarice | 25th Oct 21

    So adorable! Love outfit #3. The top looks really cute. I would love to get this for my little boy too.

  22. Lyosha | 25th Oct 21

    stylish outfits. It reminds me of the kids’ fashion show I attended yesterday. I really enjoyed the post. The clothes looks very comfortable to wear too

  23. Shea | 24th Oct 21

    Oh my goodness, he is too adorable! I love all these outfits and it makes me wish my son would still let me choose his outfits! (He just wants to wear athletic wear all the time now… not too exciting!)

  24. Yemi Edwards | 24th Oct 21

    Outfit 3 though! I love it, such a cute set! Your little person is a great model too!

  25. Allie Mackin | 23rd Oct 21

    Ah yes me too October is was always my favorite month too. All these outfits are so cute, and he looks so dashing! I so need to get to the pumpkin patch!

    Allie of
    http://www.allienyc.com

  26. Nisha | 23rd Oct 21

    They all look fantastic and perfect for fall. Great choices indeed.

  27. Lori Bosworth | 23rd Oct 21

    They are all cute, but Outfit #1 is my favourite! I love October too and all the fun things that come with it!

  28. Amy | 23rd Oct 21

    Oh my goodness! What a cutie! And I love all his outfits!

  29. Eileen | 22nd Oct 21

    There are all such adorable outfits! I love the leopard sweater vest especially! Super cute!

    Eileen | yesmissy.com

  30. jodie filogomo | 22nd Oct 21

    He’s such a styling dude Maureen. It’s impressive that he didn’t mind all of the photos.
    XOXO
    Jodie
    http://www.jtouchofstyle.com

  31. Becky, Cuddle Fairy | 22nd Oct 21

    Aw your litle man can wear any style, he is an awesome model! I couldn’t pick a favourite.

  32. Bo | 21st Oct 21

    You make dressing little boys so fun and trendy! I am a mama of girls as you know but I think having boys and dressing them well has come a long way since I had my first child 14 years ago (almost 15). There are so many cute, trendy and classy pieces for boys now days and I love that you are showcasing them for all the boy mamas out there.

    Also, I can’t wait to see what you dress up as for Halloween this year!

    bosbodaciousblog.blogspot.ca

  33. heather noire | 21st Oct 21

    Such a great selection of fall looks for boys. Love the way you styled them together. Hope you are having a great week. My birthday was yesterday, and it was the fun perfect way to celebrate the season.
    https://www.bauchlefashion.com/2021/10/trending-now-autumn-suits_21.html

  34. Lovely | 19th Oct 21

    Beautiful outfits! He looks cute in all these looks.
    xoxo
    Lovely
    http://www.mynameislovely.com

  35. Amber | 19th Oct 21

    These outfits are so fun – I think the stripes are my favorite!

    I hope you are having a great week!

    Amber

    Visit AvecAmber.com

    Follow Avec Amber on Bloglovin

  36. Shauna | 19th Oct 21

    Oh…SO cute!! I love his sunnies too. What a chic little man! And I love that you are into Halloween as much as I am! I remember you having the cutest costumes. Looking forward to seeing what you come up with this year too!

    Shauna

    http://www.lipglossandlace.net

  37. Laura Bambrick | 19th Oct 21

    These are all so cute! He is totally styling in all of them! I just love how he is rocking that leopard vest!

  38. Sheryll | 19th Oct 21

    Little man looking like a kpop trainee in all the photos!

  39. mireille | 19th Oct 21

    He looks so adorable. Love all of his outfits! I am realizing that with my youngest I am starting to like more neutrals on him. I do like his souvenir shirts but am liking things with more abstract patterns.
    http://www.chezmireillefashiontravelmom.com

  40. Jill | 18th Oct 21

    Your little man is such a cute model! the first outfit is my favorite!

    Jill – Doused in Pink

  41. Lynn | 18th Oct 21

    OMG, these are the cutest outfits! I’m not a mom yet but I 100% know that I will love dressing my kids up and also seeing what kind of fashion styles they will have! Thanks for sharing, Maureen 🙂

    Lynn | https://www.lynnmumbingmejia.com

  42. Mariann Yip | 18th Oct 21

    These are so good outfit ideas and so cute too. Thank you so much.

  43. Jennifer | 18th Oct 21

    These are all super cute!

    Jennifer
    Curated By Jennifer

  44. Kellyann Rohr | 18th Oct 21

    Oh my goodness, you have a male model on your hands! Your little man is so cute and wears these styles so well. You are blessed Maureen!
    xo,
    Kellyann

Leave A Comment

Your email address will not be published. Required fields are marked *