Hi Friends! Iā€™m Natalie Mason. I live in Charleston, SC and I am mom to Sterling 12 , Frances Moon 8 and our mini golden doodle Dolly.



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Shopping For Boys It Ain’t Easy!

Oct 15, 2012

When I first found out I was having a boy my first thought was what the heck am I going to dress a boy in?  I know a thing or two about dressing girls but boys I didn’t even know where to begin.  When Sterling was young I loved to dress him in all things traditional like bubbles and jon-jons.  Now that he is older I feel like he looks silly in that stuff now.  He no longer looks like a baby and has really morphed into a little man the past few months- a very opinionated young man at that, always wanting to choose his clothes for the day and of course it is usually not what I want him to wear!

I always thought I would continue to dress Sterling traditionally but I have actually started to like a more modern/urban look for my sweet boy.  Don’t get me wrong I still love some traditional outfits and actually love to mix traditional pieces with edgier fun pieces (think jon-jons with bright green pumas).    I never thought I would gain so much pleasure from shopping for boy stuff but I really do!  I honestly sometimes like shopping for him more than me. 

For all you moms with little boys, you know it is hard to find cute stuff.  The stores are biased and always have way more stuff for girls than boys.   I always walk in stores and there are racks and racks of girl clothes and a tiny section for boys- not fair.   There are always cute clothes up to age two but after that I find it is hard to find a good selection most places.   Boys deserve to look cute too!

My go-to places to shop for cute Boy stuff are JCrew and Gap for basics, and Zappos for shoes/Hatley pieces.  I love that Zappos has free shipping and returns.   Locally,  I love Sugar Snap Pea for Tea Collection and other great play clothes. Any other great sites I am missing out on?

Below are a few things we have purchased Sterling for Fall and I love them all.  You can’t go wrong with any of the pieces and they are easy to mix and match.

Little Man Fall Shopping

J Crew Boys French Terry| Gap Button Shawl Pullover| JCrew Long Sleeve Ringer Tee| JCrew Winter Fleece|
Gap Colored Skinny JeansTea Super Side Stripe Pants| JCrew Camp Sweatpant| Tea Collection Knit Playware Pants

I am kind of a shoe hoarder and love to buy shoes for Sterling which is funny because I rarely buy shoes for myself.  The shoes below are his line-up for fall and they are all in pretty heavy rotation.   Sterling is obsessed with his Minnetonka slippers and wants to wear them to bed everynight!  The Pumas and Converse are daily staples.  The Minnetonka Boots and Wallabees are favorites of mine (Rachel Zoe even likes the Minnetonka boots for her son Skylar).

Shoes For Little Man

 Converse High-Tops| Minnetonka Chukka Moccasin BootsHunter Rainboots
Puma Whilrwind V| Minnetonka Pile Lined SlippersClarks Wallabee

Below are a few miscellaneous items we love.  Sterling has the Hatley dinosaur raincoat and adores it.  I swear the first drop of rain and he insists he needs his rainboots and raincoat.   I swear by the Hatley pajamas too.    I love all things Patagonia.  Last year Sterling went through a weird phase where he wanted to wear socks on his hands all the time so I bought him the Patagonia Mittens to replace the socks, worked like a charm.  He still loves the mittens.

Misc Little Man

Hatley Raincoat| Hatley Dinosaur PJs| Hatley Fire Truck PJsPatagonia Vest | Patagonia mittens


Oh and because I can’t resist,  how adorable is this picture from our Halloween playgroup Friday?  My Spiderman was in full effect!



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  1. Laur says:

    Sterling always looks so cute! I absolutely ADORE all those little shoes!

  2. He is s well dressed! I keep telling my friends that I'm loving dressing and shopping for my little guy almost more than I did for my daughter because mini men clothes are so adorable!

  3. Georgine says:

    Adorable!! A friend of mine has two boys and she dresses them like little hipsters and it made fall hard for little man style! way to go on the mix and match so he cant go wrong…Zara has really unique boys clothes too. Sterling is going to be a heartbreaker for sure šŸ™‚ xoxo

  4. Zara and H&M kids are awesome too! He's a well dressed little guy!

  5. Christina says:

    I read this post title way too literally and thought you were shopping for boys as in looking for a BOY, not boys' clothing. Good god, this can only mean that I am boy crazy.

  6. You know how I feel about those bubbles and smocked things šŸ˜‰ I think Sterling looks absolutely precious as can be in his new things!! Crewcuts is def the way to go, unfortunately they don't start til 2t (though we know Fletcher is well on his way to that size). I buy a lot at Zara and Gap.

  7. Oh I just LOVE Spidey-Sterling! Boys clothes are so hard. I do love a sweet bubble on a baby but only during the first year. I might do a jon-jon or two on Tagg through next summer but that's as long as I can go. Boys clothes are so much harder. Everything is baggy and full of cargo pockets. Yuck. Although, good things can be found and then I feel really proud of myself for finding them!

  8. You should also check out Old Navy for boys. They make the cutest jeans. Colored skinnies too and much less expensive than JCrew!!

  9. Cute cute cute! I need to get that dinosaur pj's for Matthew (his obsession!) I also love Target's Circo brand, you find great staples at very reasonable prices (or cheap I should say!) Great picks Natalie!

  10. I'm all boy here so I understand the store bias-so crappy! Mini-Boden has the cutest boy clothes. Of course you can buy online but they started carrying the line at Nordstrom, too.

  11. Natalie says:

    Sterling is always dressed in the cutest clothes! I've been loving Zara baby and kids for inexpensive clothes for niece, they have the cutest stuff!

  12. Love this post! And yay for using Polyvore! Looks like you got it figured out! I'll definitely be looking to you for style tips once Ethan gets a little older. Dressing boys can definitely be fun!

  13. Alexa says:

    Love the green pumas. So cute!

  14. Jess says:

    Oh man, I'm totally bookmarking this page. I just had a little boy last Friday and I'm already finding it difficult to find cute pieces that don't have animals or some crazy saying on it.

    Thanks for the tips!


  15. Leigh says:

    I love Gap, Old Navy and The Children's Place. My child is only 15 months and he already has an opinion on what he wants to wear and he picks the "little man" modern clothes. Which is fine by me because that's what I love too! Sterling is so cute! I love that playgroup pic.

  16. kate says:

    Such cute pieces! I have a little man and just love when I can find cute boys' clothes! I'm excited for when he can start wearing the fun toddler stuff!

  17. I loved the Luigi shirts. Great longsleeve shirts without tacky stuff on them…firetrucks, bulldozers, etc…

  18. Nickie says:

    I think you have done well!! I love Sterling's fall clothes. I have a little girl and I agree that after age 2 or 3 the selection is not great. My little girl is a bit of a tomboy (which I have learned to embrace :} ) and the older she gets, the more girly and glittery the clothes selections for her age group gets. I have even been known to buy a few tops for her in the boys section. She is happy and that is all that matters. It's a different world when they can walk and talk. Enjoy the journey!

  19. Brooke says:

    Love the playgroup costumes – too cute! While I have a baby girl, I love buying my nephew SPLENDID outfits – they have the most adorable and softest pieces!


  20. Sara Mueller says:

    I think clothes for boys have come a long way! Love all the pieces in Sterling's round up. He is so cute in his Spider-Man costume.

  21. Katie says:

    Great post Natalie! Adorable pictures…Sterling is such a doll!

    I find cute things at Children's Place and the quality is pretty good. I always shop Zappos for shoes. Try Vans…the cutest shoes for boys…my two year old son is obsessed with them.

    I've been eyeing some things at Mini Boden for my little guy but haven't bought from them yet. I just bought a Hatley raincoat and boots too….he loves them!

    I thought of you this weekend when I was at Nordstrom. I got the most adorable blouse…it looks so cute on. Web doesn't do it justice. Wanted to share since you love your blouses! šŸ˜‰


    Have a great week!


  22. I am pretty much obsessed with Sterling. Such a cutie. Love his Spiderman outfit.

  23. This is my favorite post you've done! I'm pregnant with my second little man, and I'm loving dressing my 19 month old boy right now. Show us more of what you find, because we love Sterling's style over here!

  24. I think mini boden has adorable stuff for little boys, and when I lived in Italy I loved H&M, but they don't have one where we live now! I also shop at gymboree because I know I can't dress my 3 year old in cute things like dinosaurs and such for much longer! Plus, he loves their cute hats and stuff from there!

  25. Melissa says:

    Hanna Andersson and Mini Boden for durability– Hanna's, especially, last FOREVER.

  26. Jill says:

    boys are so hard to shop for and I swear the older they get the smaller their section becomes in stores like the Gap

  27. Sterling always looks cute! Love his green Pumas! Now that Jonah is 6.5, my go to's for boy clothes are JCrew, Nordstrom, Gap (though it's limited at this age), Zara, H&M and Vineyard Vines. I love the brand Peek at Nordstrom. He used to wear Mini Boden and Hanna Andersson too when he was younger. But since being in 1st grade and seeing what the older boys wear, he has become a BIG fan of anything Under Armour because they have PE three days a week and it's what all the older boys wear to school! And so it begins……

  28. Kyle says:

    Mini Boden is my favorite for James! Here are two websites for our favorite clothing stores in NYC.



  29. I have three girls and have always wanted to buy cute little boy clothes. My favorite children's store is Peek Aren't You Curious. They are having a great online sale right now. Nordstrom carries some of their items too and honor any sale prices that the store offers. I am in love with all the tshirts with the cute sayings for the boys. Check it out!


  30. Awesome array of boys clothes! We have a two and a half year old boy, too, and it can be so difficult to find cute things that aren't cheesy. One of my new go-to's (that a few other people also mentioned) is Mini Boden. Adorable stuff and great quality. Just a heads up, it runs REALLY big!

  31. Candice says:

    Loving those sweaters! I have two boys as well, and am totally on the same page about outgrowing the "classic" styles. Plus, my husband made me promise that I would stop making our soon "look like a sissy" last Christmas. But don't worry, my 9 month old has enough smocked jon jons for them both šŸ™‚

    My 3 year old wears a combo of GAP basics, Crew Cuts, Boden, and Vineyard Vines. Someone else may have already mentioned Boden and VV, but I love them both, especially Boden. All of the boys coats are from there, and all of their fun shirts are from there too – the quality is so much nicer than anywhere else in my opinion, nice and thick, but not hot. I order online, and returns are free and sooo simple. Although Crew Cuts is great in the NC summers because they are thinner and cool! Oh, and my 9 month old also rocks out in some Hanna Andersson pajamas and ski gear!

  32. I love your picks! I pretty much shop at all the same places for my son, but I am having the hardest time finding him a decent winter hat- so many of them look ridiculous! I also went to Janie and Jack today and got his holiday outfits- beyond adorable!