From Cotton Nightgowns To Leather And Lace: A Man's Guide To Buying Lingerie For Women

Indulge me for a moment while I paint you a picture.

You've been dating a woman for a little while now, and after a nice dinner, she invites you back to her place for a nightcap.

You walk into her apartment, and she offers you a drink from the kitchen. She has an extensive wine collection, some various flavored vodkas and a little bourbon.

"Cabernet OK?" she asks.

You — a gentleman — respond, "I love a dry red."

She pours you both a hearty glass of wine, and you make your way to the couch. After some small talk, you put your arm around her and go in for the kiss. She kisses back. Before you know it, things are getting hot and heavy. Your hands start wandering. But she stops you.

"Wait… let me slip into something a little more comfortable."

You've seen enough movies to know exactly what that means. As she disappears into her bedroom, you lower the lights and connect to the Bluetooth speaker. A little soft rock, maybe? You top off both glasses of wine, sit back and wait — ready for a fun night.

After five long minutes, she emerges from the bedroom. You turn, prepared to feast your eyes on whatever sexy little number she picked out, and…

Oh, you weren't expecting that? You pictured straps and lace, didn't you? Well, she said "comfortable," buddy, and that is what she meant.

Let's Talk About Lingerie

Well, now that I've failed as a romance novelist, let me share with you another story. A friend of mine was telling me about a weird dude she was dating who would hang around his house in a T-shirt… only a T-shirt. Just a Detroit Lions tee with his junk peek-a-booing out the bottom.

Somehow, that Winnie-the-Pooh outfit made him seem more naked than if he were just not wearing anything at all.

And I do apologize for the mental image, but that's kind of how women feel in sexy lingerie: even more naked and vulnerable than just being naked.

RELATED: Haters Say This Ad Campaign Is 'Regressive,' But I Say Let The Olympians Wear Lingerie

But that shouldn't be a hindrance. Because, well, lingerie is awesome. Women should feel comfortable and sexy and powerful when they wear it, and men should get to enjoy their women wearing it. 

Unfortunately, though, a lot of women don't feel that way. Especially those first few times, slipping into something tiny and strappy can instantly trigger their insecurities. To her man, she might be the sexiest thing he's ever laid eyes on, but if she doesn't see herself that same way, then what's the point?

And I want to bridge that gap. So I called in an expert — 90 Day Fiancé star Molly Hopkins, who is both a lovely human and the owner of a specialty boutique called LiviRae Lingerie in Kennesaw, Ga. And Molly agrees that leather and lace will instantly enhance your nighttime routine.

"What I tell people all the time is you have to dress up," Molly said. "You have to play. You have to keep it spicy. You have to role play."

It's tough, though, because we women are sensitive creatures. We are constantly worried about how we look and how we compare to the Photoshopped images of half-naked models on your Instagram feed (but that's a whole different issue). At some point, it's just easier to throw on some granny panties and button-up pajamas and call it a day.

"A lot of times we as women will buy things that are practical, things that we wear every day, very utilitarian, because we don't see ourselves as sexy," Molly said. "So part of the problem lies within our own self psyche.

"I feel sorry for the guys, man, I do. I feel sorry for them because they have to constantly reassure us and tell us, 'Oh, I think you're so beautiful.' Because we're not confident within our own skin."

It's Time To Spice Things Up

I've heard before that a man buying lingerie for his wife or girlfriend isn't really a gift for her — it's a gift for him. And while there is some truth to that, I'll push back a little.

Because when a woman slips into a perfect-fitting sexy little outfit that makes her feel like a stone-cold vixen, that confidence is a gift for her, too.

The question is: How do you find that perfect-fitting sexy little outfit?

So glad you asked! Because Molly dropped some of the knowledge she's gained after two decades in the lingerie industry. You want to help your lady upgrade from her Mickey Mouse nightgown? Listen up.

Hype her up.

It starts with a conversation. And that doesn't mean you say, "Hey, you're not being sexy enough." Rather, it's letting her know she is already sexy and that she should embrace it.

"We, as women, need someone else to give us permission to fulfill that side of our romanticism, and our husbands can do that" Molly said. "Sometimes we have to psych ourselves up, but I think that it's a partner deal. I think it's very important. So it truly begins with that conversation."

Of course, that doesn't mean she's going to abandon her comfy loungewear altogether. But knowing she has your support (and your adoring gaze) will empower her to get more adventurous from time to time.

Don't try to surprise her.

"The element of surprise, I don't recommend it unless it's something you truly know is going to fit," Molly warned. "Because if you buy something, and then we can't get in it, and we want to wear it for you, but we feel like a stuffed sausage… womp, womp, womp."

Guys, trust me when I tell you that lingerie sizing is complicated. Most women haven't even mastered it. In fact, it might surprise you to know that about 8 out of 10 women are currently wearing the wrong size bra.

And that's because different brands fit differently, and women's bodies come in all shapes and sizes. There is no such thing as one-size-fits-all. So even if you think you know your wife or girlfriend's size, Molly doesn't suggest winging it.

"If you just go willy-nilly to buy a size, that could cause a problem," she said. "Because if you go home and it is too small and it's too tight and not quite right, then your girl is going to feel defeated, and it's going to ruin a whole moment."

So how do you make sure you get it right?

Go shopping together.

"I think the first initial trip should be together," Molly said. "A) She's going to value your opinion. B) When we bring in that one thing that's going to just razzle dazzle them both, it's amazing what happens."

Molly explained that men and women typically gravitate toward different styles. For example, men always go for blue or white. Women usually choose black "because we think it makes us look skinny."

But if you go shopping together, you can find a whole ensemble that both of you will love.

"When I fit a woman in the right size bra and underwear, and then throw that sexy robe over," Molly began. "Then maybe you throw on a high-waisted garter belt, and now her mom tummy is a little bit cinched in. Or we throw on a little skirt that maybe covers the top of our thighs that aren't as tight as they used to be. Or we put them in a cheeky boy short that accentuates her booty a little bit. 

"When we play dress up here, we pull things that we know are going to fit your body best. And it's amazing what happens."

That's a much better mental image than that cow onesie, isn't it?

"Because all of a sudden, a man who may have been uncomfortable or a woman who wasn't ready, we just created that magic," Molly said. "And now I see him looking at her and her looking at herself, and it's like, ‘Whoa!’ 

"You can see he's lit up, she's lit up, and they're going to have a good night. There's going to come a time when she puts that on, and it's going to create that spark that they needed."

Which brings us to the next tip…

Find a reputable store.

Not all lingerie stores are created equal. 

"If you go to a jack shack or somewhere, just because it says it has lingerie, it doesn't mean that it's classy or sexy or will fit right," Molly said — adding that the clueless 19-year-old boy working the counter at the adult store is going to be very little help when it comes to making your wife feel like a goddess.

Rather, find a specialty store with a wide range of sizes and employees who know what they're doing. And that doesn't mean Target or Victoria's Secret.

"We've got to get that multi-million-dollar marketing madness out of our minds. Granted, we see these beautiful girls [Victoria's Secret Angels], but no one looks like that, and that stuff doesn't fit," Molly said. "Find a specialty boutique that carries brands that cater to multiple shapes, and they have people who are specialists at fitting lingerie, because there is a technique to it."

Plus, there are a bunch of pre-teen girls wandering around Victoria's Secret, and that's kind of a mood killer.

Have fun with it.

Once you find the right boutique, why not make a date out of it? Take her to brunch, have a glass or two of champagne and then go lingerie shopping. That's a fun time for everyone.

"I can tell you an awesome story about a couple that came into my store," Molly said. "When I first met them, he said, I want an outfit for every night of the week on our cruise. So we just kind of laid it out, and we had costumes. One night, she was the Queen of Hearts, and then another night she was this and that. And they've been coming to see me for 18 years now."

Because sexy little outfits aren't just eye candy for men. They can also add to the whole sexual experience.

"I always tell women to get a corset. We barely know how to get them on ourselves. So when you have a man taking that off, he's going to have to take a little bit longer," Molly said. "The art of undressing is very cool, right? You're exchanging the energy of touch versus just, you know, the 'wham, bam, thank you, ma'am' type situation."

Now Go Forth And Play Dress Up!

It's my goal with Womansplaining to bridge the communication gap between men and women — resulting in stronger relationships and better sex, too.

Helping her feel both sexy and comfortable in the bedroom can help accomplish both.

"I think it's a lost art of intimacy with that form of eroticism. It doesn't have to be this over-sexualized, scandalous thing. It's just, how do you reconnect with your partner in that space, right?" Molly said. "Maybe y'all put on your favorite song, you have wine, however you set the mood. Or you go on a staycation in your hometown, and y'all role play a little bit. Taking that time together is so important."

If the woman in your life would like a free online bra fitting with Molly, she has graciously passed along a code for OutKick readers: NEWBRA24.

And maybe refresh your own underwear drawer with some new boxer briefs while you're at it. Because if your lovely lady is getting all dolled up for you, she deserves something nice to look at, too. That means not your 10-year-old boxers full of holes. Or — God forbid — your Winnie-the-Pooh outfit.

Just For Fun

Just before getting married, I did exactly what Molly was talking about — I went shopping with some girlfriends and treated myself to a bunch of lingerie that made me look and feel like a bad b*tch. Then, I did a boudoir photo shoot and gifted the album to my husband on the morning of our wedding.

And while most of those photos are not for public consumption, I'll leave you with this behind-the-scenes laugh:

It's a good thing I'm better at writing than I am at underwear modeling.

Womansplaining is a weekly column about dating, marriage, sex and relationships that runs on Wednesdays.

Email your thoughts, questions, stories and gripes to Amber.Harding@OutKick.com or tweet her @TheAmberHarding.