I get a lot of questions that more or less start with "How do I....". These questions range from topics including how to learn makeup to how to walk in stilettos to plucking up the courage to go out of the house and everything else in between.
My answers tend to be kind of straightforward and usually out of someone's comfort zone. Therefore my responses don't really seem helpful and overtly obvious.

But I do think that stripping down a question to the most perfunctory essence can help us from not overthinking.

How do you learn makeup? Book a makeup lesson at a local salon.
How do you walk in stilettos? Buy a pair of two inch pumps, practice, and work your way up.
How do you find the courage to go out en femme? Grab your purse and drive to the mall. You won't "find" the courage, you just have to do it.

A LOT of this is really about being pushed out of the nest and learning to fly. Trial by fire, if you will. You learn to swim in the pool, not on the deck.

I understand there is the emotional and psychological aspect to all of this. YES, booking a makeup lesson IS probably the most efficient, effective, and logical answer if you want to learn makeup, BUT there are also all the feelings and fears that go with that. Almost all of this, whether getting a makeup lesson or choosing the right breast forms is out of our comfort zone. But we need to accept that. We have to acknowledge that if we want to be who we are then we need to take the steps towards that. We need to leave the familiar, the safeness, and the world we know if we want more than what we have.

We have to acknowledge that if we want to be who we are then we need to take the steps towards that.

Today I want to talk about shopping. I mean, BIG surprise, right? But let's talk about HOW to shop. I feel I am a bit of an expert in this because I have been shopping for femme clothes for decades. I hate to put it like this, but I have been shopping for my clothes in the days before the internet and before self check out. The very idea that I can buy everything from lip liner to a satin, floor-length ball gown to five inch stripper heels from my own home is literally amazing. It would have changed my teenage life. Self-checkout is also wonderful. I don't have to interact with a cashier at the chain store when I need to buy stockings.

The anonymity of these options is heaven sent.

As much as I love shopping online, there is nothing like shopping in person. Why? Oh let's talk about the benefits.

• You really don't know what's out there. When I shop online it's usually because I am looking for a specific item, whether it is a leather corset or a pencil skirt. When I am at the real, actual store something else entirely may catch my eye and I am inspired by something new
• Sizing can be tricky when it comes to femme clothes, and the internet isn't always helpful when it comes to finding what fits properly. Returning clothes online is an option (for most things) but it's a hassle sometimes. Seeing something in person (and trying it on) gives you a much better idea if it fits
• Mannequins and store displays are wonderful when it comes to creating an outfit. I am bad at this, lol. I'll see a cute skirt but I might have no clue what to pair it with. I have many outfits in my wardrobe that were created by buying exactly what the mannequin at the mall was wearing

Again, I understand the apprehension we may feel when it comes to all of this. Shopping for femme clothes in real life, especially while presenting as masculine is SCARY. I get it. We already stand out, right? We are a guy looking at dresses, not something very common, right?

So, how do you do it?

Well, stop looking creepy.

What I mean is that if you are looking at different skirts and the like but you are trying to be discreet, you'll fail. People will notice you TRYING to be discreet and you'll probably draw suspicion and more attention than if you just, you know, take your time and look for a cute skirt. I see too many guys hunched over, trying to be smaller, trying to avoid being noticed, while they look at heels. This gives off weird vibes. Not because a guy is looking at heels, but why are they acting so weird while doing it?

Remember, there is nothing louder than someone trying not to make a sound.

If you need to, fake it. Pretend like you belong. Again, you don't see a lot of men shopping for women's clothes, but if that guy looks relaxed, comfortable, and, well, NORMAL, then it becomes a little less uncommon.

If someone offers to help, let them. Be friendly. Once you stop pretending that you are buying a dress for your sister then you'll really get the guidance you need.

You may also get approached by a sales clerk. This happens for a couple reasons. One reason is that you've gained their attention by acting creepy or suspicious. I mean, shoplifters try to avoid being seen, right? If you are behaving the same way as a thief then the store will be keeping an eye on you. Another reason is the sales clerk wants to help. It's their job after all.

When this happens, be friendly. If you are just browsing, tell them that. "Oh I am just looking, thank you!" If you respond in a creepy way or standoff way, then you just garner more attention. Besides, being friendly is the best.

But if you are looking for something, tell them. "I'm looking for a pair of black pumps". You'll likely be taken to the right section. Wandering aimlessly can be frustrating. It's also likely the clerk will offer to help even further such as inquiring if you're looking for a certain size or who you are shopping for.

At this time just drop the pretense. They have opened the dialogue about shopping for yourself. Clerks don't believe that you are shopping for a bra for your wife. Clerks don't believe that you and your wife are the same dress size.

More importantly? They do not care. You are not the first guy shopping for women's clothes and you are not the only guy shopping for women's clothes and you are not the last guy shopping for women's clothes.

If someone offers to help, let them. Be friendly. Once you stop pretending that you are buying a dress for your sister then you'll really get the guidance you need. Once they know who you are shopping for, and once you know that they know, then it gets easier. You'll feel more comfortable (or at least less terrified) asking for a recommendation about what size you should wear or what accessories go with the skirt you're looking at.

And yes, this is out of your comfort zone, but what has staying in your comfort zone given you?

So, what happens if this doesn't go as well as you want? Leave. Don't make a fuss, just leave. You don't HAVE to shop there. There are other options.

And yes, this stings, and yes, this is the validation of our fears and hesitations, but so what? Not everything goes how we want it to, regardless of our gender identity or gender presentation. Not everything lives up to our expectations. That's life. Shake it off, learn from it, go somewhere else. Stop giving up. None of this is easy, BUT it gets EASIER.

Love, Hannah