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How To Look More Feminine When You’re A Masculine Woman (With No Fashion Sense!)

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Here’s a short story about how a tomboy like me tried to change her wardrobe and faced the difficult challenge of living up to the common kikay (girly) standard. 

Are you up for the journey, too? Then this post is for you!


Before, I never cared about how I looked. I grew up with little rascals called ‘brothers’ and a strict, unexpressive family, which revved up my preference for boyish outfits.

So, if there’s something I disliked dearly, it was wearing sleeveless tops, shorts, and makeup.

Yes, denim pants were the staple of my fashion, if you can call it fashion at all, and I’m not fond of showing too much skin.

It wasn’t a problem before because I worked in a heavily male-dominated industry, which was automotive, so wearing tight clothes was not even an option.

Nobody commented that I looked ragged. No one told me I should get a manicure, pedicure, or do my hair.

Wearing oversized polo shirts was my go-to style, along with a bare, oily face. Lol.

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Finally, Got Role Models

But two years ago, in 2022, I saw the epitome of femininity when I met my partner’s side of the family, especially the ladies.

I started to be conscious of what I wear. While I wore my brothers’ old polo shirts, they wore fashionable and kikay attires I’ve never dared to touch.

Long story short, they inspired me. Truly, I simply needed more women to teach me how to do it because no one taught me how to be ladylike at all.

So, in these past years, I’ve been testing out girly attires. It was a hit-and-miss, like buying an oversized polo that doesn’t fit with my flabby arms. Or trousers that pop my tummy out.

I would be face-palming because I really thought it would suit me, but surprise, surprise, they didn’t.

It’s a long journey to tap into the feminine side, but if you’re willing, here are some ways I did to improve my almost irredeemable fashion sense. I hope these tips will help you too!

How To Dress More Feminine When You’re A Tomboy

1. First, stay clear out of T-shirts.

Back then, if you told me to dress well, I would just buy a black T-shirt with a cool print, that’s it. Birthdays, parties, meetings – I managed to attend them all with my ol’ black shirt and denim pants.

However, as I got more in touch with my feminine side, I soon realized that T-shirts must go for a while, and I needed to explore other clothing types. Here’s how I started:

Be familiar with your body size.

Your fashion sense will highly depend on your body size and shape. I have a pear body type, and as mentioned, I have flabby arms and, yeah, a popping belly, baby!

That said, I looked for clothing styles that complement and accentuate my body shape.

What I did:

At first, I started to wear layers – adding cardigan on a sleeveless top, and replacing my denim pants with high, tie-waisted shorts.

Free A Woman Holding a Green Plant Stock Photo
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It looked good!

I tell you, once you start exploring attires and find something that looks good on you, it will snowball. The key here is to explore, try, and feel good with what you wear.

Now, I have evolved into someone who fancies maxi dresses, denim skirts, and puff sleeves.

It’s not a one-step leap to changing your style, but a whole journey to find what really gives you comfort. Took me two years to evolve from a tomboy to dress-loving girl!

Pay attention to colors.

As I tried multiple styles, I realized some colors don’t flatter my skin tone. I have morena skin and only realized I looked bad in beige after attending my best friend’s wedding.

Ha. I felt the dress, but I looked dull when the photos came out. Meanwhile, powder blue, gray, mustard yellow, and black colors looked good on me and made me look brighter.

I haven’t tried color theory for my skin undertones, but you can either try that or just experience wearing multiple styles and figure them out!

2. Buy skin care products.

In the Philippines, we have a popular phrase called “Tiis-ganda,” which means enduring pain in pursuit of beauty.

I used to find such culture a hassle. It icks me how much time and effort women spend to make themselves beautiful. Like, really? You gotta spend thousands on skin care products?

Well, all those years, I denied beautifying myself and stuck with “simplicity is beauty” and chose comfort.

But now that I’m nearing my 30s, I realize how I embraced too much comfort to the point where meeting important people feels embarrassing. I don’t look presentable at all!

My face was oily, and my skin – legs and arms – were DRY. Go figure how that worked out. It doesn’t!

So, to be more feminine, beauty is one of the priorities. I worked on the habit and discipline of caring for myself.

Still, I don’t have a crazy skincare routine but here are some products I can suggest to have better skin:

Most importantly, it takes discipline and consistency. Make sure you stick to a routine and make it a constant habit. No turning back!

3. A Visit to the Salon

Okay, this is pretty scary for someone not used to getting prepped up in a salon.

You see, I’m very frugal. I trim and polish my nails at home, and let my sister trim my hair. Saved me years of money!

But indeed, the world didn’t end when I tried to go to a hair salon, either.

I admit I was scared I would be judged because I’m like a cavewoman. But when we get used to it, it’s actually nice. You feel your self-esteem raging and build up your confidence as a woman.

I felt beautiful! Lol.

You can get your nails done every two weeks and fix your hair with styling, dye, or hair treatment every 3 to 6 months.

My friends recommended I get some facial cleansing every month, so I will try that soon, too.

It may sound like very basic advice, but I tell you, I’m far from being lady-like, and there are people like me who know nothing about being feminine.

I worked as a mechanic, and being beautiful was the last thing on my mind, so bear with me. I’m also learning!

4. Don’t be afraid to ask for fashion advice.

It’s so hard to ask for beauty advice when you’re someone who wasn’t concerned about it for the longest time. That’s how I felt, especially with makeup and face care.

It took me strength to muster up the courage and ask my friends, “What brand are you using?” or “Which derma did you go to?”

There’s a gut-churning embarrassment that I’m only asking these things at 26 years old, but well, it’s better late than never!

I noticed that store and product recommendations are very welcomed among women.

They love chitchatting about it, and when I got drawn into it, it’s actually more interesting than I thought! Just ask the right friends, and they’ll definitely help!

Watching fashion and makeup gurus on YouTube is an amazing addition to your checklist, too.

There, you could get more comprehensible advice from people with the same body shape and face features.

5. Find a comfortable style for you.

When you’re so used to dressing manly, it could feel a bit embarrassing to dress up like an “it girl.”

If you feel the same way, remember this: you don’t have to be that shining, shimmering celebrity.

Truth is, forcing yourself into an attire might backfire because clothes you’re not used to can drag down your confidence.

So, point out which style you want best. You don’t have to be too trendy. Just find a fashion that accentuates your features and boosts that feminine energy!

I, myself, can’t stand the popular mini and strappy attires. I can’t endure the hassle of limiting my movements just for beauty. Instead, I came to love crop tops with ¾ sleeves and 1950s swing, flowy, or midi skirts. Pretty modest, and I’m loving it!

Free Smiling Girl in Straw Hat Sitting on Rocks Stock Photo
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Here are my 5 tips if you’re a tomboy like me and want to slowly tap into your feminine energy. I hope this gave you insights.

Thanks for reading!

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