30 answers

Dress up Ideas for Boys

My daughter's best friends are twins. One if a girly girl and the other is a hardcore tomboy. They LOVE to play dress up but the tomboy often feels left out because we have little options for boyish dress up. We have the princess field well covered, but I am trying to find new ideas for boyish dress us clothes.

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So What Happened?™

Thank you so much ladies! These are all great ideas. I wanted to clear up that both twins are girls, so three girls total. One of the twins is a rough and tough girl that doesn't want to dress up as a princess, but wants to play with the two girls. I know that girls can be heros too, but princesses can be and often are protrayed as heroines as well. My daughter can be a girly-girl one day and a tomboy the next, so I didn't want to make the costume SO different that she would fight about it and someone would be stuck in a tutu that didn't want to be. :( I can't really go drop $20 per outfit x2-3 outfits for each new costume topic, so I needed some ideas on how to streach the budget. Thank you so much.
I was once a tomboy and hated being forced into dresses.
I definatly want to take advantage of the halloween sales, while getting the most bang for my buck. Now I feel like I can go pick out some great pieces without blowing my budget and still allowing some creativity. Thank you all again. Such creative minds!

Featured Answers

You could try going to a thrift store and picking up ties, dress shirts, etc. Remember to look in the kids and teens sections and maybe you could find suits and such closer to his size.

2 moms found this helpful

Assuming you are referring to dress up for a boy (sorry, I always thought the term 'tomboy' refered to a rough & tough little girl)...

train engineer
cowboy
super hero (anything with a cape!)
king
robin hood
peter pan
wizard
astronaut
navy officer
airforce pilot
pirate
racecar driver
football player
fireman/policeman
doctor

2 moms found this helpful

I have found superhero stuff (Spiderman, Batman, etc.), fireman, policeman, carpenter hard hats and belts, baseball/football, etc., men's ties/hats/shoes, halloween type costumes, knights...

You can find stuff and get creative at second-hand stores and garage sales: crazy hats, etc.

1 mom found this helpful

More Answers

You could try going to a thrift store and picking up ties, dress shirts, etc. Remember to look in the kids and teens sections and maybe you could find suits and such closer to his size.

2 moms found this helpful

Assuming you are referring to dress up for a boy (sorry, I always thought the term 'tomboy' refered to a rough & tough little girl)...

train engineer
cowboy
super hero (anything with a cape!)
king
robin hood
peter pan
wizard
astronaut
navy officer
airforce pilot
pirate
racecar driver
football player
fireman/policeman
doctor

2 moms found this helpful

I have two boys (4 & 6). They aren't hard core sports guys! They love to dress up. I keep all their old halloween costumes in a trunk. If you look on craigslist.com or ebay...list costumes from the lowest price to the highest. I found fab bumble bee costumes last year for .99 & 4.99!!! But you can take advantage of the timing to stock up on cool dress up (used) costumes! There are tons of bugs, pirates, sports uniforms, safari stuff, race car drivers, cops & other various emergency personnel. I like to call those 'community heroes'. There is no end to what you can find for 0.99 on ebay!! Also, they have some things @ dollar stores & Big Lots. I found a lady bug set & butterfly set...just the antennae headbands & wings for like 3.99 a set. Best of luck!

Oh, I have also spray painted their old shoes to match the Halloween costume of the year. Don't know why I felt the need to add that...

1 mom found this helpful

Is this a boy or a girl? By tomboy, I would assume you mean girl. I would go for some gender-neutral attire, like pirates (they don't have to be boys!), super heroes, fire fighter, police person, magician. There are lots of things. Check out places after Halloween to find some deals on costumes. I don't think "suits and ties" are necessary for a tomboy. Just because she doesn't want to be a princess doesn't mean she wants to dress as a man!

1 mom found this helpful

I have found superhero stuff (Spiderman, Batman, etc.), fireman, policeman, carpenter hard hats and belts, baseball/football, etc., men's ties/hats/shoes, halloween type costumes, knights...

You can find stuff and get creative at second-hand stores and garage sales: crazy hats, etc.

1 mom found this helpful

Knights...go very well with Princess

1 mom found this helpful

Hi W.
I have boys & they love to play dress-up. I I always get them extra costumes after halloween.
Boys are easier to please (I think) in this area. You can do rodeo attire, pirate swords, (cardboard & tin foil) bandanas, sunglasses, etc... I hope this helps.

1 mom found this helpful

I have a little boy who loves to dress up as well - pirates - he loves them and its easy to do: cut up an old white Tshirt, tie a red bandana on his head, make a fake sword out of cardboard and foil, and draw a pirate beard/mustache with black eyeliner on his face. Also make him a shield with foil and cardboard so he can be a knight with a sword. He can also dress up like a cowboy or a superhero with an old towel made into a cap. Also check the stores (Party City, Target and Walmart) after Halloween ususally their costumes go on clearance and you can find great deals on boy dress-up items. Good luck!

1 mom found this helpful

There are some great ideas here. I love how everyone is thinking outside of the box and including "career" options -- one that I didn't see here that I've seen in catalogs is Astronaut! Think in gender neutral terms -- doctors, business professionals, vets, president -- with an emphasis on fun! My 5 yo girl and my 6 yo nephew love playing "office." I set up a "pretend" desk with some blank folders and other office supplies. I set up an old keyboard and mouse and drew a computer monitor on a cardboard box. The LOVE it. We also set up a "store" with a pretend checkout counter and cash register. Boy, you wouldn't believe what they sell out of there -- elephants and fairy dust; tires and shoes! Go to the dollar store and have fun!!!!

1 mom found this helpful

Little boys' dress up is all about the hats!! Get an assortment of old hats - baseball caps, cowboy hat, construction hat, police hat, army cap....the list could go on and on. Round that out with a few old men's shirts and some bandanas and vests, and you have a dress up set that any tomgirl would dig right into. You might even use those clothes as a lesson that girls can do anything as well as boys! (In fact, usually better!)

1 mom found this helpful

I have boys and they LOVE superheroes...capes! Also, pirates are fun...you can get some hates, etc. at Hobby Lobby.

1 mom found this helpful

Hi W., My youngest son likes to dress up too. I found him a vest, chaps, and cowboy hat and he also has a pirate costume and a knight costume. The vest and chaps came from the internet but the others came from various stores towards the end of October when Halloween stuff is on sale. I bought them a little big too so he would not outgrow them quickly. Also, can you try resale shops. The one I go to has costumes now.

1 mom found this helpful

My 3.5 year old son loves to dress up in superhero costumes. Spiderman, Batman, Superman, Power Rangers, etc. You could also do things like pirates, doctors, and cowboys.

1 mom found this helpful

Magician is an alternate option.

1 mom found this helpful

You could try little police man or fireman outfits. Also, after Halloween is over you could grab some discounted Spider-Mans or Batman.
You could also get some button down shirts and ties to let him put on to be like "Daddy" or a business man.

1 mom found this helpful

I am not sure what you are looking to spend, but you can get tons of costumes now that it is Halloween. I would go to Party City or Walmart and go crazy. Also, a friend of mine makes a pirate tutu costume. It is girly and tomboy mixed into one. Her web site is www.totallytutus.com. Have fun!

1 mom found this helpful

My 5 year old daughter is a tomboy and isn't interested in the princess thing. She loves to play veternarian and has a little white doctors coat and stethascope (sp?) that she is always wearing. She plans to be a vet for Halloween. She will wear her white coat, stethascope and have a little puppy in the pocket of the coat. I am also going to make a little name tag for the coat with puppy foot prints and her name saying she is a vet. Hope that helps and good luck! It is hard with a tomboy because everything with girls is very pink and princessy these days.

1 mom found this helpful

Hi W.,
Baseball, football, fireman, policeman, performer, rock star. HTH, C.

1 mom found this helpful

Blue jeans, boots, cowboy hats, hard hats, bib coveralls, tank tops. Think about what our husbands like to wear.Women also work in the field now and their are women Dr.'s Vet's etc. Remember women have been holding down many jobs just not the ones that men think they should do. We are wives, mothers, maids, etc. and they all have uniforms in the work field. This is a fun time for kids. Let her pick out something that she wants and then get several. Good luck

1 mom found this helpful

Cow boys and indians, right now is the time to hit the costume section or even a bit later when everything goes on sale. All the monster and animal costumes, pirates, they can still be skirts on the pirate, cowgirl, and indian costumes so the other girls will want to play with those too! Clown, puppie dogs, think outside the box. Think back into the fiftys when they didnt have just princess outfits they had make belive!! Good luck and its super nice that you are trying to include her. I assumed you were looking for a tomboy which would be a girl but after reading the other responces I am not so sure!!! oh and farmer too!

1 mom found this helpful

You could get some gardening work gloves and a straw hat. A face mask and rubber gloves and/or a pair of scrubs, for a medical professional. Good Luck.

Pirates, police officers, chefs, construction workers, firemen, clown, superhero, etc....

You might think of animal costumes such as monkeys, dragons, tigers, etc... Also, Speed Racer seems popular since that's what my 3 year old will be this Halloween. You can have a driver for the princess.

Best wishes!

There are some not too expensive things that you could maybe get..

Toy swords (I have even seen girly princessy-looking swords), a fireman hat, a lab coat (to pretend to play a doctor, or anything else in a lab coat) something black (like a ninja) a cape (multi-purpose!)..

Those are just some ideas off the top of my head.

Doctors, indians, police officers & pirates could be for girls that don't want so much pink and lace.

Oh wow where do I start!!! There are so many! Firefighter, Police officer, Paramedic, Nurse, Doctor, Construction worker, Chef, Military. There are so many options, and it's halloween season so you should be able to find most of those costumes and accessories. Litte girls don't always have to be fairy princessess. The can be Hero's!

You are in luck now that it's almost Halloween;-) Plenty of things to choose from..try fire fighters, pirates and policeboys;-) or Spiderman, power rangers or other cartoon characters..enjoy! ;-)

an inexpensive white dress jacket (with pockets)will cover the gamut from doctor, to chef to waiter to vetrinarian (make sure to have a couple of props available for each idea)

A tailored shirt and a simple red cotton scarf can go from Tux like dress up to swash buckling pirate to a prince..

Hats of any and all styles (get from good will and be sure to spray with rid and let sit for a week to be sure no pests are not infesting them) are ALWAYS a hit with kids, they can allow a kid to pretend to be a baseball player to a newspaper reporter to a spy.

A large t-shirt (with a cut up the center of the front) or silky dress shirt for a woman with a silky scarf makes a great kimono.

Also, another way to encourage your tomboy to have more fun with the dress up clothes is to ask the girls to put on a play using as many different costumes as possible. The tomboy will usually be great at directing it as well as enjoying the more boyish roles...

Good Luck...

My tomboy daughter loved to play dress up as a clown, doctor, firefighter,etc. We had even gotten a little cardboard haunted house at Hobby Lobby and spray painted it white. That thing was used as a house, doctor office, vet office, spaceship, grocery store, etc, until it just wore out with much duct dape holding it together (and some foil from its days as a spaceship)!

I'll bet if you tried you could find a "Super Woman" costume. There's lots of Super Hero costumes out there as well as sports costumes. But, really, why can just plain ole blue jeans and shirt work? She'ed probably be happy in that.

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