Our XDress Journeys: Riley

The Origin

When did you first start wearing panties or lingerie, and what made you want to move away from traditional men’s underwear?

I started with my wife’s panties. Curiosity first. Then it just felt better than anything I owned. Softer. Closer to the body. More fun to look at. Traditional men’s underwear always felt like a compromise after that. Boxy. Built to hide you. Once I felt something pretty sitting right on my skin, boxers started feeling like a downgrade. I wasn’t trying to become someone else. I just found underwear that made me want to get dressed.

The first real shift was private and simple. I put on a pair that was not designed for me, looked in the mirror, and liked the person looking back more than I expected. Then I wore a pair under regular clothes and spent the whole day knowing something prettier was there. That secret is what hooked me. Comfort is what made me stay.

The Turning Point

Can you describe the specific moment or product when you went from just "trying" lingerie to fully embracing it as part of who you are?

 It stopped being “trying” the day my wife treated it like a good thing instead of a secret. She noticed. She commented. She enjoyed the surprise of it. That’s when it clicked. Lingerie wasn’t a costume. It was part of how I showed up.

The other turning point was fit. Victoria’s Secret gave me the pretty. Finding pieces actually cut for a male body is what made it wearable all day. XDress especially. Once the pouch, rise, and stretch made sense, I stopped fighting the clothes and started wearing them like they belonged. After that, I didn’t go back.

The Routine 

How has wearing lingerie shifted from a "special occasion" habit to an everyday staple for you—and how do you decide what to wear on any given day?  

It’s everyday now. I don’t save it for a night out or a mood. I put a pair on when I get dressed, the same way I put on a shirt.

I pick based on mood and what I’m doing. Soft and simple for work or long days. Something cheekier when I want to feel a little extra. Pretty prints and satin when I want to feel seen, even if nobody else sees it. Sometimes I pick a pair because I know it’ll look good later. That’s half the fun. Sometimes you just want to surprise your man with some new lingerie. Best of both worlds. I get to feel good all day. She gets the reveal.

Styles & Fabrics 

What are your favorite lingerie styles and fabrics, and why do they feel right for you?

Victoria’s Secret when I want that classic pretty look. HUNK when I want a sharper, body-conscious fit. Away / Anchors Away when I want something cute and playful. XDress when I want lingerie that was actually built for me.

Thongs and cheeky cuts are the ones I reach for most. They sit right. They show the shape I’ve been working on. They disappear under clothes without bunching. Satin, microfiber, stretch lace. Floral prints. Solid reds and blacks. Soft pastels when I want something sweeter. If it looks pretty and still lets me move, I’ll wear it all day.

The Fit Factor

Lingerie designed for male bodies often requires different support or sizing considerations. What fit or sensory details (like seam placement, pouch support, or waistband stretch) make or break a piece for you? 

Fit makes or breaks it. Pretty does not matter if it fights you. I need a pouch that holds without crushing, a waistband that stays put and doesn’t roll, and seams that don’t sit in the wrong place. Enough stretch to move. Enough structure to stay shaped.

Women’s cuts can look great on a hanger and still fight male anatomy in real life. Too small in the front ruins the whole day. Too loose in the waist feels sloppy. That’s why brands designed for men matter. When the rise, pouch, and stretch are right, you forget you’re wearing anything fancy. Until you catch the waistband in a bathroom mirror and remember why you bought it.

Self-Expression & Identity

Some men wear lingerie to tap into their softer or feminine energy, while others just view it as better-fitting, more aesthetic clothing. How do you view the relationship between your lingerie and your masculinity or identity?

It’s both. Lingerie lets a softer, flirty side out. It also just looks and feels better on me than traditional men’s underwear. I don’t think those two things cancel each other out.

I can be the guy I am in regular life and still like pretty underwear. Wearing it does not erase that. It just means the version of me under my clothes is more honest. I used to overthink what it “meant.” I don’t anymore. It means I like how I look and feel in it. My wife likes it too. That is enough identity for me.

Openness & Relationships

How open are you about wearing lingerie, and if you share your life with a partner, how has your journey played out in your relationship? Do your friends know? 

I’m open with my wife. That’s the important part. She is not just okay with it. She is into it. We shop. We pick things out. She notices when I have something new on. Sometimes I wear it for me. Sometimes I wear it for her. Sometimes I want both.

Outside of her, I’m selective. A few people know pieces of it. Most people don’t need to. I don’t owe the grocery store my underwear story. I do owe my partner honesty. The relationship got better when it stopped being a secret I was managing and became something we could actually enjoy.

Impact on Confidence

Beyond comfort, how has wearing lingerie impacted your overall confidence or everyday self-expression?  

It changed how I carry myself. When what you’re wearing underneath looks good, you stand differently. You walk differently. You stop treating your body like something to hide. I get compliments on my shape. I notice I don’t hide as much.

The confidence is quiet most days. Nobody else has to see it for it to work. But when she does see it, it lands. That loop is hard to beat. I feel good. She responds. I feel even better.

Advice to Your Younger Self

If you could go back in time to the day you bought your first pair, what wisdom or reassurance would you give your younger self?   

Stop overthinking it. Buy one good pair. Wear it around the house. See how you feel before you build a whole story about what it means.

If you have a partner, tell them sooner than you think you should. The right person will meet you there. The wrong person was going to be a problem anyway. Don’t cheap out at the start. A pair that actually fits will teach you faster than ten that don’t. And if you like it, let it become normal. Normal is where confidence lives.

Also: surprise them later. New lingerie is a gift you get to wear first.

The XDress Community

What does XDress mean to you, and how has it supported your lingerie journey?

XDress matters because they make lingerie that looks like lingerie and still fits. That sounds simple. It isn’t. A lot of pretty underwear is made for a different body. A lot of men’s underwear is made to be invisible. XDress sits in the middle. Feminine on purpose. Cut for men. Wearable every day.

Seeing other guys talk about daily wear, partners, and confidence made the whole thing feel normal. I’m loyal to a few brands, but XDress is the one that made “this is for me” feel obvious instead of borrowed.

Thanks, Riley @bibottomboi