Cool Boyish Outfits for Every Occasion

Let’s break gender norms together! Switching up your style from feminine to traditionally “boyish” is exciting, especially if it makes you feel more like yourself, but can be daunting when entering new situations such as work, going on a date, or going to the beach. You might feel a little bit out of your comfort zone at first, but we are here to help inspire you to wear cool “boyish” outfits everywhere! If tomboy outfits make you feel more like yourself, don’t think you have to wear feminine clothes (I sure don't).

There are so many benefits to wearing boyish outfits, regardless of your sexuality, sex, or gender identity. Traditionally boyish clothing is more boxy, comfortable, and can be really stylish in on a variety of body types. You can wear cool boyish clothing on a casual weeknight, on a date, and even to work. Here are some cool boyish outfits for multiple occasions that you will love from street style to beachwear. 

The Business Casual Outfit 

For some of us, dressing like ourselves in a work setting might be nerve-wracking, in this case as a woman dressing in a tomboy style, chances are many of the women around are dressed in feminine attire. I personally love to shake things up in formal settings with a cool boyish outfit like this - black pants, a belt, a white button-down shirt, and a chain necklace. If it is colder out, I will layer it with a matching blazer. 

Nothing feels more badass to me than a woman wearing a suit to work. You will feel in charge in this boyish workwear outfit, and your co-workers may even give you compliments on this sharp look. Shop around for some menswear-inspired shoes like these, which totally make this look perfect. 

The First Date Outfit

Going on a first date can be terrifying, but knowing that you look great will make all of your fears disappear. When I want to feel confident and put together, I usually throw on a leather jacket. A leather jacket is both casual yet nice enough to wear out to dinner or a bar.

Underneath you can wear a nice t-shirt or button-up, black jeans or pants, a belt, and your choice of shoes. For a sporty look, try a pair of athletic sneakers. For a more edgy nightlife vibe, opt for a pair of combat boots. Either way, you will look awesome in this cool boyish outfit you can wear on any date for confidence your partner will love. 

The Beach or Pool Outfit

Rocking swim trunks and a sports bra to the beach or pool can be really comfortable and cute. You can find a lot of different men’s swim trunks online to choose from (we are working on creating a women’s swim trunk at MNSTRM) A pair of athletic boxers underneath will give even more "boyish" vibes.

You can also wear your trunks with a bikini top. Some days, I wear a full bikini with swim trunks over it so I can take them off if I decide I want to get a full body tan. Either way, you’ll feel great at the beach knowing you don’t need to wear a specific type of swimwear and can have both masculine and feminine elements in your outfit.

Summer Time Outfit

Ah, the summertime. So many different choices for a cool boyish outfit. You could rock light-colored baggy ripped jeans, khaki pants, or basketball shorts on the bottom and a graphic tee, white tee, or button up on top.

We love this outfit that has a pair of trunks on the bottom, in case you decide to hit the beach or pool, with a blue and white striped button-up. White sneakers are a perfect way to finish off any summer boyish look since they are bright, clean, and match almost everything.