I enjoy finding clothes for my sons to wear much more than I expected to. I take pride in the fact that people notice how nice they look, even as my personal style has become largely characterized by granny sweats and bags under my eyes. It's also rewarding to see my boys take an interest in their appearance and express their personalities through what they wear. I'm not a very girly-girl in some ways, but I was really looking forward to dressing a girl at some point. When I had two sons, I thought that I was going to have to wait until my siblings or friends had daughters in order to play dress up, but Ishmael loves nothing better than when I buy him new clothes and he proudly picks out his own outfits too.
On the other hand, I did not expect Ishmael to take such an interest at such a young edge, expressing distaste for some of the clothes I would like him to wear. It's hard to know when I should let him do things his way, and when to put my foot down about my boys wearing certain items they don't want to wear "just because". For example, not wanting to wear vintage sweaters is understandable because they're often itchy (I can usually talk them into putting something on just for a picture), but if they can't tell me why they don't like something, especially if they were fine wearing it last week, I'm more likely to override their preference. This often ends in tears, which is frustrating for everyone, so we're still working on how to navigate some of these personal style vs. hygiene vs. practicality battles.
I don't want their appearance to be something that either I or they obsess over. I want them to be comfortable and able to actually live in their clothing, and I don't want to raise them thinking that people who don't enjoy putting a lot of effort into their outfits are "less cool" or lazy or whatever other labels I might be tempted to affix to the less clothes-loving population of parents and children. Style has everything to do with personal choice and personal taste. It's 100% valid to put your energies elsewhere.
From that, it follows that the most basic key to dressing boys in a stylish and interesting way is to actually take great interest in the task, and that's not a priority of everyone's. (Why can't cleaning the house be a passion of mine too?!) Although it's much easier than it used to be, I still think that dressing sons in a practical yet non-dorky way takes more effort than it does with girls. It's certainly doable, but I thought I'd share some of my tips and tricks for those who have commented on how much they like what my boys wear. Oh, and this should go without saying since we're the near-penniless children of missionaries and hippies, but I'm very much a budget-conscious stylist/shopper! I don't have an actual budget for clothes at this point, but almost never do I buy something at full price. I buy clothes for the boys as they need them or if I see a good deal or something especially cool. They do have a lot of clothes, but what Ishmael has gets passed to Ira, and what Ira grows out of we pass on or save for cousins or resell.
First of all, my ground rules are no white and no text. It truly boggles my brains why people bother even making children's clothes in white! Or is it only my children who stain everything they touch?! Putting boys (and I assume girls, too) in white clothing might as well being burning dollar bills, in my book. I also file this under "dressing practically" because it's sad for parents and children alike to have to say "please don't play in the dirt" or "lean over your plate!!!" (10,000x) just to try and save a white shirt. I did buy Ishmael one shirt that has blue crocodiles on a white background because I loved it so much (so does he) but I make him take it off at every mealtime. Clothing shouldn't restrict play or other daily activities, in my opinion. Some exceptions are made for special occasions, but then you have to be willing to see an item ruined on the first wear. I've more or less given up wearing white or pastels as a parent of toddlers either.
On the subject of clothing with text on it, it's very difficult to do this "right", in my opinion, so we just stay away from it altogether. Text on children's clothing is usually ridiculous ("TRUCK LOVER" or "Auntie's favorite red-headed wonder".... please! This is cute to no one but you) or inappropriate. There are certainly snarky or funny words on kid's clothing that I think is funny sometimes, but the fact is that it's not the child choosing to make this statement, it's the parents. Snarky or funny things on shirts almost always offend someone, so why make your child the object of that sort of attention when they don't really understand the message they're wearing across their chest anyway? To be honest, I generally extend this rule to myself too. I very rarely see someone else's shirt with text that I think is tasteful.
I think my only other advice, beside where to find good boy clothing, is not to confine shopping for boy's clothes to the boy's section of stores or websites. I "cross dress" my boys all the time, and no one knows, including my boys. Clothing made for girls is often slimmer and more colorful, which are both style choices, not really gender-related. Putting my boys in girls pants is a life-saver - both of my sons have long skinny legs and no rump to speak of, so their pants are often much too big in the waist but not long enough. Target sells pants that have that nifty elastic-and-button system inside the waistband so that you can adjust the waist, but if you have trouble finding the right proportions in other brands, definitely take a look in the girls section. I do double check to make sure that back pockets don't have floral stitching, rhinestones, buttons with overly feminine designs, or lining that is obviously for girls. Girls also have a much better selection of leggings, which is very helpful especially for younger kids (crawling stages) because regular pants and jeans tend to be bulkier and have strange proportions that make movement (and even getting dressed) more difficult for babies. To this day, Ira prefers the two pair of [girl] leggings he has, a black and white geometric print and a red plaid, to all his other pant options.
Now, I will share some "secrets" of where to shop for cool clothes for boys. I am not shy about asking people where they bought something that I see their kids wearing. I screenshot it on my phone if it's something I see on Instagram, and then I search for a gently used version online. Some accounts (like @fancytreehouse) have already tagged the brands they're wearing, so you can tap on the picture and find all the sources. Sometimes in order to get a cheaper price you have to wait a while to until the item is out of season of several collections old (like at Target or GAP for example, which have limited runs of each style), but I don't mind that.
I used to buy a lot of clothes for the boys on Instagram from other moms who love to thrift or who are selling off clothes their kiddos have outgrown. Since Instagram moved to the algorithm system about a year ago, buying and selling on Instagram is not as convenient, but many sellers have moved to other platforms where you can still find them, and there's not as many people trying to go after what is still available on Instagram. If you haven't bought on Instagram before, the basic rules are commenting on something you want with a comment like "sold" or "me please" and then the seller will send you an invoice via paypal (after you provide your email via direct message). I haven't utilized this very much, but if you know what you're looking for, you can search Instagram by hashtag, such as #minirodiniforsale.
I don't think I've ever bought clothes for the boys on Ebay, and maybe one item on Etsy, but that's an option. Etsy is expensive and Ebay is hard to navigate, in my opinion, and hard to find items on. I prefer the Kidizen app which is exclusively for children's items. You can enter the sizing and gender preferences of your children (or not - you don't have to set parameters) and search all kinds of kids clothing, mostly gently used. You can also search by keyword or hashtag if you know exactly what you want. Many sellers are willing to negotiate on prices or bundle (a discount for buying multiple items) if you ask (same on Instagram). Some, particularly on Instagram, are willing to trade as well. I use Kidizen to resell too, but I like being able to specify the size I want which you can't do on Instagram. There is SO much cute stuff in the 12 month to 2T range in vintage clothing and even regular clothing, but kids tend to be harder on their clothes in the 3T-5T range, so less vintage clothing from that size bracket has survived the past several decades, and less of it is in good enough shape to resell, even if it's a modern brand. Snatch up something you like if you see it in that size!
I do love to thrift shop, but I don't find many clothes (especially in the 3-5T range) that I like for my boys while thrifting. You have to sift through a lot of junk to land on anything good, and I don't usually have the time or energy. The last time I was in the Whittier Savers thrift shop, they had organized their clothing by gender and size and I actually found quite a few great pieces! But that is rare for me. Also rare, but sometimes you hit on a great pile of stuff (vintage, mostly) that has come in as one donation. If you find one thing you like, it's worth checking on the racks close by in case there are more items donated by the same person. The rarest of all, in my experience, is finding a good stash of vintage kids clothing at estate sales, but those are usually the best - in good condition and all in one spot! I like many vintage styles (often well made and not dorky), but vintage sizing is often considerably smaller than modern sizing. If you're buying vintage online, make sure to go by the actual measurements provided (almost all vintage sellers will offer them), not the vintage tags. Another cool thing about vintage is that not many people want it, so once you have a trained eye and/or dress your kids in vintage, people will start bringing it to you.
Consignment stores or events can be good too. I haven't utilized the stores around here very much (they are quite small), but especially when I was shopping for smaller sizes, the Moo La La Boutique that happens twice a year at the Santa Maria fairgrounds was amazing. There are a few sellers who have styles I really like, and the clothes are tagged with seller numbers, so you can kind of shop by style in that way. I find that foreign brands (Japanese and French, in particular) are often stylish and they are affordable on consignment, especially since most people don't want to buy something they don't recognize, so these really good pieces can be on the cheaper side! Having a non-mainstream style can be challenging, but as I mentioned above, you have less competition when you're trying to buy stuff and it's so exciting when you do find things you like!
I do find some things at GAP, HandM, Old Navy, and Target too. They all have good sales from time to time, so I stock up on basics like tshirts or solid colors or shoes to mix and match with the more unique things I find elsewhere. For some reason, I have a bit of a mental block against used pajamas, but luckily there are some pretty cute ones at GAP, for example.
If you pay attention when buying used clothing on consignment or online, you might start to notice some boutique or even designer brands that you lean toward as well. Again, I never buy these brand new, but if you hunt around, you can usually find affordable used ones. Some that I like are Harajuku Mini (was a line at Target), Tiny Whales, Prefresh, Tea Collection, Mini Rodini (pricey, even secondhand!), and Zara. I'm sure there are more I'm forgetting. My favorite Instagram shops sort of morph as my kids grow and our styles change, but we love @chalkmarks, @lovedthreads, @pipsqueaksinplaid, and @mini_fresh_hawaii to name a few. Both chalkmarks and minifreshhawaii are very popular, so you have to be very speedy (and turn on notifications for their shops on your phone) if you want to buy from them. I think I'm following about 1000 shops (not all for kids, but many are) on my Instagram shop account @retroriot, so if you're really committed, you can start there and see what catches your eye.
Happy hunting!
On the other hand, I did not expect Ishmael to take such an interest at such a young edge, expressing distaste for some of the clothes I would like him to wear. It's hard to know when I should let him do things his way, and when to put my foot down about my boys wearing certain items they don't want to wear "just because". For example, not wanting to wear vintage sweaters is understandable because they're often itchy (I can usually talk them into putting something on just for a picture), but if they can't tell me why they don't like something, especially if they were fine wearing it last week, I'm more likely to override their preference. This often ends in tears, which is frustrating for everyone, so we're still working on how to navigate some of these personal style vs. hygiene vs. practicality battles.
I don't want their appearance to be something that either I or they obsess over. I want them to be comfortable and able to actually live in their clothing, and I don't want to raise them thinking that people who don't enjoy putting a lot of effort into their outfits are "less cool" or lazy or whatever other labels I might be tempted to affix to the less clothes-loving population of parents and children. Style has everything to do with personal choice and personal taste. It's 100% valid to put your energies elsewhere.
From that, it follows that the most basic key to dressing boys in a stylish and interesting way is to actually take great interest in the task, and that's not a priority of everyone's. (Why can't cleaning the house be a passion of mine too?!) Although it's much easier than it used to be, I still think that dressing sons in a practical yet non-dorky way takes more effort than it does with girls. It's certainly doable, but I thought I'd share some of my tips and tricks for those who have commented on how much they like what my boys wear. Oh, and this should go without saying since we're the near-penniless children of missionaries and hippies, but I'm very much a budget-conscious stylist/shopper! I don't have an actual budget for clothes at this point, but almost never do I buy something at full price. I buy clothes for the boys as they need them or if I see a good deal or something especially cool. They do have a lot of clothes, but what Ishmael has gets passed to Ira, and what Ira grows out of we pass on or save for cousins or resell.
First of all, my ground rules are no white and no text. It truly boggles my brains why people bother even making children's clothes in white! Or is it only my children who stain everything they touch?! Putting boys (and I assume girls, too) in white clothing might as well being burning dollar bills, in my book. I also file this under "dressing practically" because it's sad for parents and children alike to have to say "please don't play in the dirt" or "lean over your plate!!!" (10,000x) just to try and save a white shirt. I did buy Ishmael one shirt that has blue crocodiles on a white background because I loved it so much (so does he) but I make him take it off at every mealtime. Clothing shouldn't restrict play or other daily activities, in my opinion. Some exceptions are made for special occasions, but then you have to be willing to see an item ruined on the first wear. I've more or less given up wearing white or pastels as a parent of toddlers either.
On the subject of clothing with text on it, it's very difficult to do this "right", in my opinion, so we just stay away from it altogether. Text on children's clothing is usually ridiculous ("TRUCK LOVER" or "Auntie's favorite red-headed wonder".... please! This is cute to no one but you) or inappropriate. There are certainly snarky or funny words on kid's clothing that I think is funny sometimes, but the fact is that it's not the child choosing to make this statement, it's the parents. Snarky or funny things on shirts almost always offend someone, so why make your child the object of that sort of attention when they don't really understand the message they're wearing across their chest anyway? To be honest, I generally extend this rule to myself too. I very rarely see someone else's shirt with text that I think is tasteful.
I think my only other advice, beside where to find good boy clothing, is not to confine shopping for boy's clothes to the boy's section of stores or websites. I "cross dress" my boys all the time, and no one knows, including my boys. Clothing made for girls is often slimmer and more colorful, which are both style choices, not really gender-related. Putting my boys in girls pants is a life-saver - both of my sons have long skinny legs and no rump to speak of, so their pants are often much too big in the waist but not long enough. Target sells pants that have that nifty elastic-and-button system inside the waistband so that you can adjust the waist, but if you have trouble finding the right proportions in other brands, definitely take a look in the girls section. I do double check to make sure that back pockets don't have floral stitching, rhinestones, buttons with overly feminine designs, or lining that is obviously for girls. Girls also have a much better selection of leggings, which is very helpful especially for younger kids (crawling stages) because regular pants and jeans tend to be bulkier and have strange proportions that make movement (and even getting dressed) more difficult for babies. To this day, Ira prefers the two pair of [girl] leggings he has, a black and white geometric print and a red plaid, to all his other pant options.
Now, I will share some "secrets" of where to shop for cool clothes for boys. I am not shy about asking people where they bought something that I see their kids wearing. I screenshot it on my phone if it's something I see on Instagram, and then I search for a gently used version online. Some accounts (like @fancytreehouse) have already tagged the brands they're wearing, so you can tap on the picture and find all the sources. Sometimes in order to get a cheaper price you have to wait a while to until the item is out of season of several collections old (like at Target or GAP for example, which have limited runs of each style), but I don't mind that.
I used to buy a lot of clothes for the boys on Instagram from other moms who love to thrift or who are selling off clothes their kiddos have outgrown. Since Instagram moved to the algorithm system about a year ago, buying and selling on Instagram is not as convenient, but many sellers have moved to other platforms where you can still find them, and there's not as many people trying to go after what is still available on Instagram. If you haven't bought on Instagram before, the basic rules are commenting on something you want with a comment like "sold" or "me please" and then the seller will send you an invoice via paypal (after you provide your email via direct message). I haven't utilized this very much, but if you know what you're looking for, you can search Instagram by hashtag, such as #minirodiniforsale.
I don't think I've ever bought clothes for the boys on Ebay, and maybe one item on Etsy, but that's an option. Etsy is expensive and Ebay is hard to navigate, in my opinion, and hard to find items on. I prefer the Kidizen app which is exclusively for children's items. You can enter the sizing and gender preferences of your children (or not - you don't have to set parameters) and search all kinds of kids clothing, mostly gently used. You can also search by keyword or hashtag if you know exactly what you want. Many sellers are willing to negotiate on prices or bundle (a discount for buying multiple items) if you ask (same on Instagram). Some, particularly on Instagram, are willing to trade as well. I use Kidizen to resell too, but I like being able to specify the size I want which you can't do on Instagram. There is SO much cute stuff in the 12 month to 2T range in vintage clothing and even regular clothing, but kids tend to be harder on their clothes in the 3T-5T range, so less vintage clothing from that size bracket has survived the past several decades, and less of it is in good enough shape to resell, even if it's a modern brand. Snatch up something you like if you see it in that size!
I do love to thrift shop, but I don't find many clothes (especially in the 3-5T range) that I like for my boys while thrifting. You have to sift through a lot of junk to land on anything good, and I don't usually have the time or energy. The last time I was in the Whittier Savers thrift shop, they had organized their clothing by gender and size and I actually found quite a few great pieces! But that is rare for me. Also rare, but sometimes you hit on a great pile of stuff (vintage, mostly) that has come in as one donation. If you find one thing you like, it's worth checking on the racks close by in case there are more items donated by the same person. The rarest of all, in my experience, is finding a good stash of vintage kids clothing at estate sales, but those are usually the best - in good condition and all in one spot! I like many vintage styles (often well made and not dorky), but vintage sizing is often considerably smaller than modern sizing. If you're buying vintage online, make sure to go by the actual measurements provided (almost all vintage sellers will offer them), not the vintage tags. Another cool thing about vintage is that not many people want it, so once you have a trained eye and/or dress your kids in vintage, people will start bringing it to you.
Consignment stores or events can be good too. I haven't utilized the stores around here very much (they are quite small), but especially when I was shopping for smaller sizes, the Moo La La Boutique that happens twice a year at the Santa Maria fairgrounds was amazing. There are a few sellers who have styles I really like, and the clothes are tagged with seller numbers, so you can kind of shop by style in that way. I find that foreign brands (Japanese and French, in particular) are often stylish and they are affordable on consignment, especially since most people don't want to buy something they don't recognize, so these really good pieces can be on the cheaper side! Having a non-mainstream style can be challenging, but as I mentioned above, you have less competition when you're trying to buy stuff and it's so exciting when you do find things you like!
I do find some things at GAP, HandM, Old Navy, and Target too. They all have good sales from time to time, so I stock up on basics like tshirts or solid colors or shoes to mix and match with the more unique things I find elsewhere. For some reason, I have a bit of a mental block against used pajamas, but luckily there are some pretty cute ones at GAP, for example.
If you pay attention when buying used clothing on consignment or online, you might start to notice some boutique or even designer brands that you lean toward as well. Again, I never buy these brand new, but if you hunt around, you can usually find affordable used ones. Some that I like are Harajuku Mini (was a line at Target), Tiny Whales, Prefresh, Tea Collection, Mini Rodini (pricey, even secondhand!), and Zara. I'm sure there are more I'm forgetting. My favorite Instagram shops sort of morph as my kids grow and our styles change, but we love @chalkmarks, @lovedthreads, @pipsqueaksinplaid, and @mini_fresh_hawaii to name a few. Both chalkmarks and minifreshhawaii are very popular, so you have to be very speedy (and turn on notifications for their shops on your phone) if you want to buy from them. I think I'm following about 1000 shops (not all for kids, but many are) on my Instagram shop account @retroriot, so if you're really committed, you can start there and see what catches your eye.
Happy hunting!
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