Tips For Guys Wearing Women’s Jeans

In a previous writing I discussed my new found interest in blending my wardrobe and wearing some pieces of women’s clothes in public. During my online searches for alternative ways of dressing I found a lot of folks asking if guys can wear women’s clothes. Now who knows what they meant by this. Some were probably interested in venturing out and expanding their self-expression. Others still, were probably trying to make their shame someone else’s problem by policing gender.

For those hoping to branch out and find women’s clothes to wear then yes, you can absolutely put on something cute and flit about town. Since I have some experience in this, I thought I was in a key position to help men out in their quest.

For those who feel the need to police how others may dress; see a therapist.

I must caution that I have resorted to generic terms of men and women, masculine and feminine, for the sake of clarity. However, make no mistake that if these labels don’t fit you, then trust me when I say that I see you.

I’m going to begin talking about pants because I think that is an easy way to introduce a piece of women’s clothing into your wardrobe in a more subtle way than a shirt or a dress would be. Because we often slowly explore things rather than jumping straight in with an entire wardrobe, this seems like a good place to dip in the proverbial painted toe. So let’s start at the top and work our way down by learning a little about women’s pants.

As you will soon find out, I will be referencing the penis and testicles fairly often as that is a chief issue with form and function when crossing clothing styles. So don’t get squeamish on me now.

Where to shop

The only way you are going to know what size works for you is to try some things on. When I started crossdressing I bought things discreetly online. I’m also on a budget so that often means getting things preowned from places like Ebay. The key here is to find sellers who actually do the measuring of their garments. If you buy new from online or even online auction sites, just go to the clothing manufacturer website of the item you are thinking of purchasing and use the size chart to your advantage.

You’ll need to pick up a clothing measuring tape (also used for body measurements) to find out what your actual measurements are. Clothing sizes are wishful thinking at best.

If you are in the store, finding your size is much easier and probably cheaper in the long run. Grab a couple of sizes that you think are approximate and head to a dressing room. 

Waist

In women’s clothes waist size is a series of numbers that has nothing to do with any real world number. I find that I may be anywhere between a size 4 and an 8 depending on which brand and style I have in my hands. It’s infuriating. It would be great if all clothing manufacturers actually used real world measurement as a size. Nothing is true in clothes anymore though and we carry shame about the actual measurements of our waist in part because clothing manufacturers are doing stupid shit like this. 

However, here we are so this means you’ll have to know your actual measurement if ordering online. Do not use the size of your men’s pants because that shit ain’t real either. The men’s jeans I buy list a 28 or 30 waist, but my actual waist measurement is closer to 32 inches.

Stretch fabrics will also measure differently than non stretch fabrics. Within the same brand you may find that a size 6 for instance will fit you in a stretch jean but will require a size 5 in regular jean fabric (or that scenario in reverse).

Some pants, generally non-jean materials, have a size of small, medium, large and so on. The manufacturer’s size chart is a good tool here if you can’t try these pants on in person.

If you’re going to try things on in a store then knowing your measurement isn’t as important as you can just try them on and go from there.

Rise

The rise in a pant is the measurement from the bottom of the crotch to the top of the waist band. There is ultra-low (rare nowadays but popular in the late 90’s), low, mid, high, ultra-high (popular as of this writing and goes by various names).

Low rise works for some guys but others will find it uncomfortable. If you are thin and a low-rise waist doesn’t create a muffin-top kinda scenario for you then you might find this style a good fit. 

An unintentional benefit of these pants is that because they have less distance between the bottom of the crotch and the top of the waistband the zipper is placed lower and takes up a greater area of the front of the pant which makes standing to pee a bit easier. However, the low rise also means it’s a short zipper so it’s still not the easiest feat when it comes time to go fishing for your penis. 

While you’re wearing low-rise pants, bend at the knees and squat to the floor. Where do the pants go? If they start to make you look like a handyman who could use suspenders then go with a pair of pants with a higher rise. You could also look for a low rise style which doesn’t fit snug on your upper thighs which can sometimes contribute to pulling your pants down during such a maneuver. However, I’m not here to yuck your yum, so you do you my dear. 

If the pants stay mostly in place and require very little repositioning when you stand up then this could be a good rise height for you. Even with little movement, I still prefer to wear a belt with low rise pants just to help keep things in place. It keeps the pants snug on my butt, which makes me look better and also gives me a way to accessorize by adding a masculine or feminine flare.

Mid rise is probably where most guys will be comfortable. Pants with this level of rise sit where most people (aside from your 90 year old uncle Harold) wear their pants. A mid rise pant will move around less when bending over as well. I’m guessing that a belt here is still most people’s friend, but you’ll know more about that when you try them on.

High rise pants are a bit of a mystery to me. I don’t have the body type to make these look good. Even if I did, my main concern would be function. Women’s high rise pants often still retain a  small zipper but it is positioned even higher than most other style pants. That means that your deliciously naughty bits sit below the zipper behind a piece of fabric generally bisected with a seam. So if the seam pushes too far up you can end up with a moose knuckle look. Now I am a fan of seeing curves in this type of scenario but it may not be your thing so just keep that in mind.

The other concern is that a higher zipper placement means nothing is lined up to pee whilst standing. You’re going to have to drop trow in order to make that happen. Welcome to a woman’s world.

The other issue with high waisted pants is that they are made for wider hips and a narrower waist. Flaunt it if you got it, but most guys are not built like this so I could see how the fit could miss the mark on multiple fronts.

Leg/Fit Style

Flexibility can be an issue for a number of the styles we are talking about here. Try a pair on, raise your legs, squat down, and just get a sense of how much flexibility you will have. I love how some jeans look but have passed on getting them due to a lack of functionality.

Skinny/Jeggings

Skinny jeans are those which generally hug your legs from start to finish. These also include jeggings which are extremely stretchy jeans that fit like leggings. Be careful with jeggings because a tight fitting ankle is often easy to slide on, but difficult to get back off when dealing with larger feet and ankles. I do not recommend a low rise in this style as crouching will always pull the pants down.

Additionally, while jeggings can be made of extremely stretchable fabric they are often too tight to allow complete free range of motion when raising your legs or bending down. I am extremely thin but even I find these uncomfortable. The flexible fabrics also double to serve the wearer with a mission impossible; positioning your genitalia in any way that could be considered aesthetically pleasing. So while these might be fun around the house (something I still don’t find to be true) they lose utility whilst going about your day.

Bootcut and Flare

These are pants which get larger towards the leg openings. Men’s pants have boot cut options so that style is not a foreign concept for most guys. Flare pants generally have a larger leg opening still and will definitely denote to others that you are wearing women’s pants. It’s a stylistic choice for both of these and some are more subtle than others. Generally these pants fit tighter on the upper leg and relax more as they go down, but each brand is different.

Wide Leg

Similar to boot cut and flare but more relaxed through the thigh and often have a flare at the bottom. Width can vary from slightly wide to extremely wide based on style preference.

Straight

Pretty simple. Just as with guys pants these are a straight shaped leg from start to finish. If you want a feminine look but still retain just a hint of that mysterious and wonderful androgyny then try these as they are also slightly relaxed.

Mom jeans

Yup, here we are. These are jeans that generally have a high waist but a more relaxed fit through the thighs and legs. Some taper toward the leg openings and others are more of a straight leg. It is a broad category and each manufacturer has their own variation on this loosely defined style.

Boyfriend jeans

Like mom jeans, this one is hard to nail down, but these generally hover around a mid-rise waist and have a more relaxed fit somewhere between straight and wide leg. However, like mom jeans, designers are mixing and matching to such an extent that it is hard to tell what you’ll end up with in terms of rise and leg style.

Leg length

Finally something we can talk about that is simple. These run the gamut of petite/short, extra/short, petite, short, regular, long, tall, x-long, and so on and so forth. The best way to find this out is to measure your inseam and use fitting charts online or try them on in the store. Interestingly, leg length is usually accurate so the inseam listed on your guy pants should transfer over to the size chart for women’s. While we are deathly afraid to know our waist size apparently we have no such qualms about the length of our appendages, well . . . most appendages.

Cautions

So here are the extra little things you should know about women’s jeans. 

The tighter the fit through the hips then the less room you will have for your genitalia. I buy pants that fit fairly snug through the hip area. While walking I do not notice anything but I am used to being cradled by brief underwear anyhow. If you wear boxers, yawn . . . sorry I drifted off there for a moment, then this will be a much different transition for you. 

Sitting down is another thing altogether. Things get a bit tight but I honestly enjoy the feeling. It’s a reminder of what I’m wearing and I’m not uncomfortable, rather I’m just getting used to a different fit. I don’t notice it much anymore but I still wouldn’t want to wear them for a 12 hour cross country drive. For most situations they work just fine. Your results will vary and there is no way to know until you give it a go.

I alluded to this but allow me to say outright that your underwear selection matters … a lot. Those boxers I mentioned before are not going to work. In fact, just throw those out all together, you’re not doing anyone any favors. In boxers you are hanging free which means that the seam in women’s pants are pretty much going to position everything to one side or another which isn’t going to look good at all. Something that holds your bits in a pouch is going to be much better as everything will stay a bit more centered. All briefs are not created equal. I have found that the tighter a pair of underwear holds me in place then the better off I am wearing them with my women’s jeans. Still, there is no ideal positioning unless you’re going to tuck entirely. Something is going to favor one side or another. For me I just try to minimize it as much as possible but then embrace whatever I can’t hide.

If you are doing a low-rise jean then some underwear may creep above the waist band. This could be a style that might work for you if your undies are fashionable and less so if your waist band says Fruit of the Loom. Luckily, briefs also come in different rises so if this is a continued problem I’d try a lower cut.

A tighter pants fit also gives a better look at your butt. The drawback here is that the lines your underwear creates can be problematic. Jock-strap underwear may create a dented line where your butt meets your legs as can some briefs. Plus if your goal is to show off your butt (and I have long thought that it should be) then, in my opinion, a thong is the way to go. The pants will be able to cradle each butt cheek without the added resistance of a full panel of fabric from conventional underwear getting in the way. This will allow your posterior to have as much definition as possible.

The other drawback is pants that make your butt look awesome are also just as form fitting in the front which leaves no room or flattering way to position a penis and however many testicles you have. It’s an unfortunate reality, but here we are nonetheless.

Women do benefit here by having seamless underwear. Unfortunately, those will not work well if you have a penis as the lack of seams just allows everything to fall out. 

If you’re going to go the full crossdressing route or are transitioning then there are what they call gaffs to help hold everything in a more concealed position, but I do not have experience with these so I cannot comment further. There is also a company called FIT4U Solutions that claims to have compression underwear without the need for tape or gaff. Again though, I have no experience with these.

The most functionally infuriating thing is pocket space. Women have been rightly complaining about this for years. This is something that you need to check out when you’re trying on pants. Some styles have so little pocket space you’ll wonder why they are even there (some pockets aren’t there). I have a small minimalist wallet the size of a debit card and I can barely fit that into my back pocket. My keys, also minimalist, occupy an entire front pocket. My phone, which is a smaller model (notice a pattern here), sticks out of the other front pocket. Admittedly, I like my phone showing on the front because it is what I’m used to seeing when women wear those pants. Therefore, it makes me feel more feminine. In reality, it’s simply a result of poor design. If I was doing anything with a lot of movement I wouldn’t feel that my phone was safe, but it’s fine for just strutting around.

Color

The last consideration is color. Conventional wisdom says that if you’re looking to conceal some of your masculine lines then dark colors will help accomplish that. I think that’s true but you also have to like how you look in them and so if you find a pair of jeans that you really like and they are in red, white, or whatever then I say just go for it. Wear what makes you feel good luv.

There you have it. I hope I have covered everything you wanted (pun partially intended). Folks with penises can absolutely wear women’s jeans. In fact, my opinion is that these bodies look all the more dreamy in femme fashion. I also vote for letting your bulge show, but given that I really need to work on controlling my drooling in public, I’ll leave that choice up to your preference and comfort level which is all that really matters anyway.

Go out, have fun with it, and let your femme flag flutter like a summer dress in the breeze.