The Tomboy LookBook

Here’s to you, The Tomboy.

You may not necessarily dress “like a boy” but you have mastered how to style clothes from the men’s department to fit a woman’s wardrobe.  You are simply inspired by male fashion trends like a great tie, vests, and loafers. 

You can take a shirt from your boyfriend’s closet and style it seamlessly into your own outfit.  You can make a men’s baseball tee look like a million bucks.  And you can rock the hell out of masculine jackets and slouchy jeans. 

Now I, personally, don’t think the name tomboy is fair because people automatically paint a picture of a butch woman who wears baggy pants and oversized tee shirts.  In my eyes, I’d rather say you’re style sense is menswear INSPIRED, a much more positive word.  Inspiration can come in all shapes and sizes, but to grasp the opposite gender’s fashion world and make it your own takes a whole new level of skill and style knowledge. 

I was a tomboy most of my life actually, and now-a-days....even with the few pink pieces and sequin dresses that hang in my wardrobe, I still relate the most with the relaxed style of a “tomboy”.  To me, there is nothing more fulfilling than a great comic book hero tee, ripped jeans, and Chuck Taylors.

Now let's dive into TomBoy Fashion.  Outfits with baseball caps and baseball tees, camo print, letterman jackets, and so much more. Let’s get to it ladies! :)

'My Boyfriend's Shirt'
Now out of all of today's looks, this one is the most stereotypically male because we're actually wearing clothing straight from the men's department, of Target to be exact.  I know this look may catch some of you off guard but to be honest, I haven't been this comfortable in a long time.  This look is very much throwback Viktoria, from my earlier years in my life before I found my calling for fashion.  I used to straight up dress like a guy, and one of my go-to outfits was a screen tee underneath a button up shirt, jeans, and chucks.  I've always had a love for converse, and a love for men who wear converse too haha, so in my opinion a pair of classic black and white lo-tops is a must for any self proclaimed tomboy.  When you get a little too hot in this outfit, you can tie the over-shirt around your waist, and carry on with your day.  It's quick and simple, just like guys like it.  For some added flair though, I flipped my faux leather baseball cap backwards and added fun zipper jewelry so that, ya know....people do realize I'm a woman. 
Shoes: Converse / Pants: Target / Tank: Forever21 / Camo Shirt: Target Men's / Baseball Cap: Target / Zipper Jewelry: Aria & Forever

Another form of Tomboy can be the sports fanatic.  This woman probably has more jerseys and team shirts than she does normal clothes.  Well, she at least has a good collection going, like myself. If there is ONE THING that I will always choose over going shopping, it's a good game. Primarily football, but basketball is a close second.  As a huge Jordan fan, I will buy pretty much anything Bulls.  So yet again, I'm straight up wearing a shirt that was borrowed from the boys, and guess where I got it, yup...Target Men's department.  A great way to show your team pride yet stay chic and polished is by layering that team shirt under a blazer, then pairing the look with your favorite jeans and comfy boots or sneakers.  I added my chunky chain necklace for some boyish bling and called it a day for my second, low maintenance look. 
Jeans: Target / Combat Boots: Endless / Top: Target / Blazer: The Limited / Necklace: Forever21

'Letterman Take 3'
The third form of "tomboy" that I'm showing you all today is the jock. Not to be confused with the sport fanatic tomboy, this woman actually plays sports or maybe even did in an earlier time in her life.  I myself, ran Varsity track for 4 years in HS and almost went to college for it so seeing this faux Letterman jacket (or Varsity outerwear) trend take off like crazy could not make me happier.  We've already seen this jacket make a brief appearance on the blog with my articles 'How To Style Menswear' and October Alphabet Trends: 'C is for Collegiate'.  Today,  however, we're playing with layering four menswear pieces over each other so that the tomboy element is very apparent.  Lets start with the shell to the whole look, we're wearing a pair of distressed shorts, a gingham shirt, and my Nike sneakers, all of which are pieces that men can wear their own versions off.  Then, to add icing to the whole outfit we topped it all off with a men's tie, which any woman can borrow from her boyfriend, guy friend, or ever her dad, and the signature faux letterman jacket for a pop of color.

Shoes: Nike / Denim: Old Navy / Gingham Shirt: Thrifted / Jacket: Charlotte Russe / Tie: Borrowed

Shop The Looks!
Like what you see? Simply click on the pictures below to purchase the same or very similar pieces from the outfits above.,990

So now let's get down to a few basics that you might want to ask me....

Q: If I'm just browsing, what things should my eye look for? 
A: If you're shopping, you might want to look for fuss-free pieces that are 1.) versatile and 2.) easy care, let me explain. If you have a tomboy style, you probably have a laid back mentality which means when you are getting ready in the morning you don't want to have to fuss over what pieces to pair together, so look for items that are either solid colors, basic patterns like stripes, or graphics that can pair with anything (like sports logos). Also, make sure you are buying easy care pieces so that when laundry day comes you can just throw everything in the washer and walk away. Buy cottons and t-shirts, and always hang dry. Simple as that.

Q:  What stores and brands have the best variety of tomboy fashion?
A: In my opinion, if you have the guts to do this, the best place the find tomboy fashion is in the men's department of your favorite stores. Yes, the guys clothing. A lot of my favorite casual pieces are from the men's department of stores like Target, Forever21, and JCPenney. The key is the find generic pieces like button up tops, and screen tees. Make sure you are shopping young guy's sections not the mens, essentially that is equivalent to the juniors section versus the women's section. When it comes to sports items, you can get away with the XXLs in the Boys department if you're the right size.   

Q: What are some key pieces I should invest in to really express my style? 
A: When it comes to the shell outfit for a great tomboy, 3 great things to invest in are a pair of Chuck Taylors, some distressed boyfriend jeans, and white boyfriend tee. From here you can easily dress your outfit up or down by adding casual pieces like a zip up hoodie, or dressier pieces like heels for the few days you want to flaunt what your momma gave ya.

Return to the other five styles! Click here

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