Every feminine journey begins with a spark — that quiet, thrilling curiosity to see yourself in a new light. For some, it starts with a swipe of lipstick or the soft hug of lace; for others, it’s the gentle shimmer of a wig that finally feels right. However it begins, expressing your femininity is deeply personal — and completely yours to define.

In this week’s letter, a reader writes:

“I am exploring my feminine side and would love advice on lingerie, makeup, clothing, shoes, and wigs to help me express myself authentically.”

Synne says…

This is a big question, and it covers such a wide range of topics within feminine gender expression that it’s hard to give a clear answer. For most of these, though, the key is experimenting. Since we all have different faces, body shapes, and style preferences, what works for me with makeup or clothing might feel completely different for you.

I think many of us like to start big and expect quick success (I know I do), but in my experience it’s better to start small and slowly build your knowledge and confidence. Instead of diving straight into a full glam makeover, try starting with a lip gloss you like the color of, maybe add some mascara, and build from there.

It also helps to pay attention to general fashion and makeup trends for your age group. That said, your authentic self might look very different, and that’s the best part.

Jess says….

The great thing about feminine expression is that almost each one of these elements is an infinite rabbit hole, but crucially one that you can lower yourself down at your own pace with whatever feels the most comfortable or fun to explore! YouTube is obviously a fantastic resource, whether for the learning the basics or getting into more niche, advanced tutorials, but the best advice I can give is just to experiment with whatever brings you the most joy. I personally started with clothing and a few items of makeup (lips and eyeliner), before slowly introducing the other stuff over time (I didn’t even have a wig for the first year or so). Sizing for clothes/shoes/lingerie will take a bit of experimentation, as well as any makeup that revolves around your complexion or shade, so it’s better to start cheap and then go for the big ticket, expensive items once you’re familiar with your look. Ultimately though, you don’t have to be perfect with all these skills and items – just embrace how it makes you feel and enjoy every second of the process!

Cindy says….

I think this is quite subjective! Especially depending on body proportions. I believe the staples every one should have is a nice bra and panties. If im feeling pretty bloated a good lingerie body suit is a great option paired with some stay-ups/thigh high tights (I have a few nice pair of them from the BF Store.

Makeup can be hard as well! But practice makes perfect and have some fun! I’d highly recommend getting brows cleaned up ( changes everything and lots of men go to places to get them done). I’ve just watched YouTube videos to learn.

Learn your female shoe size a big mistake for me was trying to squeeze in to a heel that doesn’t fit and in 10 mins all you want to do is take them off. I’d recommend a simple pair of stilettos ( don’t go too high at first), or a sling back (helps with sizing if you’re unsure)

And for the wig. Find something that fits your personality! The wig is you! But if you’re looking for the best fit, Try to find what your season is (skin tone) there’s lots of apps and the. I asked AI what color wigs would go best with my season/skin tone.

Biggest piece of advice though is to have fun with what you’re doing and find out what you enjoy and what you don’t like! It’s a process and very few nail it right off the bat!

Jules says…

Welcome! In terms of being authentic, its best to look at you and what suits you. For wigs what is your natural hair colour, or do you aspire to be a blonde, brunette, redhead (nudgenudge)? Lengthwise the options are endless, and depends on if you want a easy to maintain shorter hair, or long locks that need a bit more work. Makeup, again look at you, are you pale? Tanned? Do you have a favourite colour for eyeshadow, what shape is your face (weird question, but there are varieties, and they dictate products you should use). In terms of body, height, weight etc, that can help with clothing/ lingerie, and your shoe size will have a female equivalent, if not correlate. Perhaps you have a female family member you can use for inspiration, or a celebrity you admire? I hope this helps ❤!

Hannah says…

Here is my little list of my suggestions:

• Wear clothes that FIT, not clothes that you WANT to fit.
• Know your measurements
• Be realistic about your shoes. Five inch stilettos look amazing but you’ll probably regret them after an hour at the mall
• Schedule a makeup lesson at a salon. They will be able to tell you how to do makeup that works for your facial shape and structure as well as which products work best for your skin
• Invest in a wig. The key word is INVEST. There isn’t such a thing as a high quality, cheap wig. You can’t have both. A cheap wig might be easy on your bank account but when it comes to a wig, you generally get what you pay for. If you can, schedule an appointment at a wig boutique to find the right style and cut and color that works for your facial structure and shape. Long, blonde locks might look amazing on some, but it might not be the right style for your face.

Here’s the fun stuff, lol:

• Panties and bra MUST match
• A nightgown and shaven legs is divine
• The right shoes will boost your confidence like you can’t imagine

Love, Hannah

Eden says…

If you’re looking for specific advice, it’s important to figure out what you want to know, and what you want to do with it. Are you wanting to feel more beautiful when you dress at home? Are you wanting to blend in so you can spend the day shopping at the mall? Are you wanting to feel sexy and go dancing at a nightclub in a little tiny dress? Do you want to just see what it’s like to maybe… be a bustier, blonder version of yourself? All of these things have different results!

For someone who doesn’t know where to start, I always recommend starting at the beginning of brainstorming what feels right for you. (For those of you who don’t know, I have a course on Udemy on connecting with your feminine energy!) If it’s makeup tips, then YouTube tutorials or a makeup lesson might be your best friend. If it’s designing a signature clothing style, working with a fashion stylist could be the best way to improve your look. And if you don’t know where to start at all? Google’s a great place to get ideas, or maybe hop on over to Pinterest to start a vision board of what feels right to you!

Every detail — from your favorite lipstick shade to the wig that frames your smile just right — becomes part of your story. Exploring your feminine side isn’t about perfection; it’s about connection, curiosity, and joy. Let yourself experiment, play, and grow into the woman you see in your reflection.

Remember, femininity isn’t something you have to earn — it’s something you already hold within you.

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