25 Summer Tomboy Outfits That Are So Cool

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You can dress femininely and you can cross androgynously. Here is a collection of classy summer tomboy outfits to bring out your masculinity.

Conventional female outfits are so commonplace that there’s almost no fun in wearing them anymore. To that end, androgynous outfits are slowly gaining popularity with more girls adopting a masculine “tomboy” look.

If you haven’t tried wearing tomboy outfits, you’ll find it difficult to choose one for yourself. As someone who fancies androgynous outfits and actively researches them, I’ve collected 25 of the best summer tomboy outfits to step up your game.

Summer Tomboy Outfits that are So Cool

Table of Contents

Dressing in masculine outfits doesn’t excuse you from looking cool. Here are a couple of summer tomboy outfits that balance androgyny with coolness.

1. White Shirt with a Line Striped Blazer + Neutral Colored Pants + Loafers

If you interact a lot with guys that dress formally, you’ll see why this makes it to the list. The outfit gives off the necessary masculine looks while retaining a bit of alluring feminity.

White Shirt with a Line Striped Blazer + Neutral Colored Pants + Loafers
@dresseddanielle

2. Ash Hoodie with Leather Jacket + Ripped Jeans + Sneakers

Guys love hoodies, and if you’re going tomboy, you should too. While I don’t think the summer is the best time for hoodies, who dare complain when it looks this chic?

Ash Hoodie with Leather Jacket + Ripped Jeans + Sneakers
@dresseddanielle

3. White Shirt with Brown Trench Coat + Jeans + Sneakers

If you’re looking for a balance between masculinity and feminity, here’s what you’re missing. This makes an excellent work outfit and could pass in most formal events, but without the ripped jeans.

White Shirt with Brown Trench Coat + jean pants + Sneakers
@dresseddanielle

4. White Shirt with Leather Jacket + Black Tie + Black Plants + Boots + Sunglasses

I’d rather not wear a jacket in the summer, but I’d say the tie looks spot on. The entire outfit looks a bit too masculine, which is exactly what you’re shooting for when trying tomboy outfits.

White Shirt with Leather Jacket + Black Tie + Black Plants + Boots + Sunglasses
@dresseddanielle

5. Line Striped Shirt with Camo Shorts + Sneakers

What would guys wear on a casual summer day at home? Definitely a simple long sleeve shirt with shorts. Getting it right shows it’s even better on ladies that it does on them!

Line Striped Shirt with Camo Shorts + Sneakers
@dresseddanielle

6. Black Long Sleeve Shirt with Ash Shorts + Sneakers + Sunglasses

If the colors from the preceding outfit don’t sit well with you, here’s an alternative. Notice how it’s still the simple long sleeve shirt with shorts that you can wear on a casual weekend.

Black Long Sleeve Shirt with Ash Shorts + Sneakers + Sunglasses
@tendani_g

7. White Button-front Shirt with Navy Blue Shorts + Boots + Grocery Bag + Sunglasses

If you’re after something that keeps you even cooler than a simple long sleeve, why not try a button-front short sleeve shirt. This outfit offers extra comfort and chicness without subtracting from the chicness.

White Button-front Shirt with Navy Blue Shorts + Boots + Grocery Bag + Sunglasses  
@megandijkman

8. Peach Shirt with Drawstring Shorts + Loafers + Sunglasses

There’s no difference of opinion; a shirt and a pair of shorts make the perfect tomboy outfit in the summer. Here’s another idea, this time with a short sleeve tee instead of the regular long sleeve.

Peach Shirt with Drawstring Shorts + Loafers + Sunglasses
@dresseddanielle

9. White Long Sleeve Shirt with Blue Jeans + Sneakers + Sunglasses

If there was a default formal outfit for men, this would be it. Since it doesn’t have the word “male” written over it, there’s no harm in wearing it as a lady interested in tomboy outfits.

White Long Sleeve Shirt with Blue Jeans + Sneakers + Sunglasses
@roots_jsini

10. Black Top with Black Jacket + Floral Pants + Boots

If you’d rather go dark-themed, you can pair a dark top with a dark jacket for an androgynous look. Add floral pants and you’ve successfully replicated her alluring outfit.

Black Top with Black jacket + Floral Pants + Boots
@itsemmamac

11. Peach Graphic T-Shirt with Ripped Jeans + Sneakers

Guys wear graphic tees too, but you have to make it pretty loose. Find something close to what she’s wearing; to maintain androgyny, you can pair the loose tee with skinny jeans.

Peach Graphic T-Shirt with Ripped Jeans + Sneakers
@lesbeauxfits

12. Black Shirt with Black Ripped Jeans + Sneakers + Sunglasses

All-black outfits can make cool tomboy outfits too, as she illustrates in this picture. A simple long sleeve shirt with ripped jeans is enough to ace the look, with the sunglasses being an extra.

Black Shirt with Black Ripped Jeans + Sneakers + Sunglasses
@vercei_official

13. Burgundy Shirt with Black Ripped Jeans + Sneakers

While you may be thinking this compilation is full of shirts, you should also know that guys don’t have the option to wear dresses or crop tops. So, here’s another attractive shirt-jeans combination.

Burgundy Shirt with Black Ripped Jeans + Sneakers
@vercei_official

14. White T-Shirt with Belt + Oversized Khakis + Vans

A white shirt over an oversized khaki is an excellent way to flaunt your tomboy tendency. Plus, it also looks classy and is a good fit for most casual and semi-formal events.

White T-Shirt with Belt + Oversized Khakis + Sneakers +Backpacks
@newyorkersinthecity

15. Line Striped Shirt with Neutral Colored Shorts + Sneakers + Sunglasses

We’ve seen more than a dozen outfits and I’m not sure we’ve seen any this masculine. If you want something attractive, but in a masculine way, here’s an excellent idea. Just don’t wear this on a search for a boyfriend.

Line Striped Shirt with Neutral Colored Shorts + Sneakers + Sunglasses
@dddaphne_

16. Blue Shirt with Navy Blue Pants + Suede Shoes

When you pair different shades of blue, you can only get a chic outfit. While guys may have seemed to monopolize this combination, this picture is enough proof that it can also look great on ladies.

Blue Shirt with Navy Blue Pants + Boots
@tomboy_guys

17. Blue Hoodie with Black Jacket + White Oversized Pants + Sneakers + Sunglasses

Back to the good old hoodies, here’s another way to style them for a tomboy look. I personally won’t wear a jacket over a hoodie, but it looks chic and the white beautifully contrasts the black.

Blue Hoodie with Black Jacket + White Oversized Pants + Sneakers + Sunglasses
@tendani_g

18.  Blue Graphic Shirt with Blue Jeans + Sneakers + cross Shoulder Bag

Guys don’t usually don skinny jeans, and that’s an important thing to consider when dressing like a tomboy. Here is an excellent outfit idea that follows that rule without looking excessively masculine or feminine.

Blue Graphic Shirt with Blue Jeans + Sneakers + cross Shoulder Bag
@iamtunapu

19. Multi-colored Graphic Shirt with Denim Jacket + Black Pants + Sneakers

Denim jackets are undoubtedly cool, which is why they’re popular for both guys and girls. However, when you wear them a certain way, it looks more masculine than feminine, and that’s what she got right.

Multi-colored Graphic Shirt with Denim Jacket + Black Pants + Sneakers
@yeah.mckenzie

20. White Shirt with Sweater Vest + Oversized  Pants + Sneakers + Grocery Bang + Hair Cap

If you’re looking for something that makes you feel extremely comfortable, here’s an idea. However, I’d drop the bag since it gives a feminine touch to the entire outfit; guys don’t carry bags!

White Shirt with Sweater Vest + Oversized  Pants + Sneakers + Grocery Bang + Hair Cap
@nilcelerr

21. Black Shirt with Flannel Shirt + Black Pants + Boots + Sunglasses

While flannels are not the most masculine clothing items out there, you can incorporate them into a tomboy outfit. Waring a short flannel shirt with black shirt and pants give you a masculine yet chic look.

Black Shirt with Flannel Shirt + Black Pants + Boots + Sunglasses
@dresseddanielle

22. Plaid Suit with Ask Turtle Neck Shirt + Boots + Sunglasses

A plaid suit sounds like an outfit that guys would wear, and as this picture proves, it’s not terrible on ladies either. You may also want to incorporate the wristwatch and sunglasses for extra flair.

Plaid Suit with Ask Turtle Neck Shirt + Boots + Sunglasses
@dresseddanielle

23. Orange Flannel with Ripped Blue Jeans + Boots

Plaid-patterned shirts are pretty popular among guys, but you can also make it look great on you. Pairing this flannel pattern with skinny jeans will create an outfit that’s attractive and comfortable during the summer.

Orange Flannel with Ripped blue Jeans + Boots
@dresseddanielle

24. Line Striped Shirt with White Ripped Pants + Loafers + Sunglasses

When going out for a casual summer events, mixing colors and layering clothing items is pretty unnecessary. Instead, why not wear a striped shirt over ripped pants and get it over with.

Line Striped Shirt with White Ripped Pants + Loafers + Sunglasses
@dresseddanielle

25. White Long Sleeve Shirt with Tan Pants + Boots + Sunglasses

Most of the summer tomboy outfits in this compilation will look weird when worn to work. If you want something that qualifies as a formal outfit, here’s an idea that doesn’t look terrible.

White Long Sleeve Shirt with Tan Pants + Boots + Sunglasses
@dresseddanielle

And that’s all for my post on the coolest summer tomboy outfits to try. Want some more outfit ideas? Then you might want to check out these blog posts.

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