What to Do When You Dress Better Than Your Girlfriend?

What to Do When You Dress Better Than Your Girlfriend?

We enlisted professionals on this one
when you dress better, what to do, taylor's take

By Taylor Davies | Last Updated: Mar 1 2024 | 10 min read

Taylor tackles the touchy subject of what to do (if anything!) when you dress better than your girlfriend…

Even though I’ve been dropping knowledge here at SG for awhile now, I sometimes forget just how meaningful it is to hand out advice to real, living, breathing guys out in the world.

You read, you listen, and you take us at our word—which is incredible (I feel pretty powerful, tbh). I like getting to peek into the brains of the male population—I always learn something and am constantly impressed by the lack of fart jokes.

Just kidding, but really, you guys are so sophisticated…

taylor's take, when you dress better, what to do when

So—when a reader came to us recently with a big, difficult question and asked for some genuine advice—we obviously couldn’t leave him hanging. Megan shared his email with me and we agreed it was the perfect topic to tackle for the next edition of Taylor’s Take.

He wrote:

“I’m a fashion conscious guy and spend a lot of time thinking about my choice of clothing and appearance. I’m on the shorter side, with a bit of a beer gut, so I try to make sure that my hair is always neatly cut and combed, I smell reasonable, and my clothes are stylish and fit my body.

My girlfriend, on the other hand is not. She’s 5’7″ with long legs and good curves — a natural beauty. But (and possibly as a result of this) with a demanding work schedule as a young professional, she doesn’t have much interest in fashion or spend time on things like getting her hair/nails/makeup done. We both work similar hours, but our approach to the aesthete could not be more different.

Can you suggest any ways to nudge her towards putting more effort into things like fashion and cosmetics? It may come off as superficial, but to me, a neat manicure and tasteful, fashionable outfits communicate more than physical beauty. They represent a lifestyle and conscientiousness about how one presents herself. And a few simple things like this would make our relationship so much more gratifying to me. But is there anything you can actually DO when you dress better than your girlfriend?

I realize this may be an off-topic question, but I’m grateful for any insights or advice you might have on the subject.”

I’ll be honest, my first thought when I read this email was:

There’s no way this could end well for him.

I put myself in her position and imagined how I’d feel if my boyfriend told me that I could or should care more about my appearance.

My instant reaction? Something like a gut punch to my self-worth, my confidence, and my value as a partner all at the same time. There’s just no way I wouldn’t take this kind of criticism personally. My boyfriend thinks I’m gross? He thinks I’m not trying hard enough? Is he even attracted to me anymore?

All that to say, this is a delicate subject! And I would actually venture to say that delicate doesn’t even begin to cover it. A mine field? A guaranteed “tears being shed” situation? Maybe—if you don’t handle the conversation with sensitivity and care.

But here’s the great news…I’m here to help you do just that!

And that includes sharing wisdom on what to do (if anything) when you dress better than your girlfriend!

We know this guy isn’t alone in his feelings and more importantly—he’s not wrong for feeling them. SG has received a fair few letters and comments like this over the years, asking us what to do when you feel like you care more about style and grooming than your partner. It happens, and telling you to “suck it up and deal” is not how we roll at SG HQ.

Since I’m not currently in a relationship nor am I a licensed professional, I decided to seek out the advice of someone who really knows their stuff and could give some extremely qualified advice. Enter Sherry Amatenstein, LCSW, a couples therapist and the author of The Complete Marriage Counselor. Sherry and I pondered the letter together and came up with a four-step plan for this reader (and any of you guys out there pondering how to have a difficult conversation with your sig-oth).

Here’s what to do when you dress better than your girlfriend:


Immediately upon finishing the letter, Sherry’s reaction was, “I wonder first why it matters so much to him, frankly.” That right there tells you the first thing you need to know: This is more about you than it is about her.

Sherry wondered if perhaps our letter writer was feeling outside pressure and judgment about who he could attract as a mate since he mentioned his shorter stature and belly compared to his girlfriend’s long legs, curves, and natural beauty.

This is a great question, and one you might spend a moment pondering in the mirror because honestly, who among us hasn’t worried about what other people think?

Before you even think about sitting down with your girlfriend or wife and having a conversation like this, take some time to really hash out your point of view. Maybe even write it down. Ask yourself, Why do I care so much about this? Make a list of the reasons; take stock of your feelings.

Then, sit with them. If, after looking at this list you still feel like it’s a conversation that needs to be had, you’re on your way.

Since you know it’s not about your insecurities and self-doubt, you can move forward from a place of positivity. As soon as you bring this up with your partner, you’re going to need to be able to articulate exactly why her clothing, makeup and hair are important to you—and “I want other people to be impressed” is not a good enough reason.


One thing Sherry and I immediately agreed on is that you, a guy, simply have no idea what it’s like to be a woman.

You know this, but I’ll dig in a little anyway.

While a guy can do a lot less and still look awesome (shower, comb your hair and wear clothes that fit properly and voila!)—the formula isn’t so black-and-white for women. Now, I could go toe-to-toe all day about the cost of clothing and grooming products for men versus women, but that’s not really the point. The point is, it takes women longer and requires more effort to get fully ready with hair, makeup and the works.

>> Read Megan’s take on this subject!

Consider these fun facts: If she colors her hair, a trip to the salon can take upwards of four hours and cost hundreds of dollars. Just blow-drying your hair can take 30 minutes for women. Doing her makeup? That takes anywhere from five to 20 minutes. Manicures take 45 minutes at the salon, longer if you do it at home (don’t ask).

A woman who works the same demanding schedule as her male partner and wants to have some semblance of a social life very well might not have the literal time to maintain the kind of appearance you have in mind.


If you already know all this and you still feel like you want to discuss the topic with her, here’s how Sherry suggests you begin.

First, start in a complementary tone. Tell her you value her opinion. Then say something like, “I know I care a lot about my appearance. What do you think about the efforts I take?”

I know that sounds a little clunky but awkward conversations have awkward intros sometimes… So just go with it. Next you might ask, “What about you? You’re such a natural beauty, but do you feel like you care a lot, or as much as I do?” Maybe suggest going shopping together and see what she says.

From my perspective, these questions are a great way to test the waters. You get to explore the topic without much risk of starting a fight, and you’re inviting her to share her opinion, which is great.

As long as you’re fully prepared for step four, I think you can definitely have a constructive conversation that won’t end in screaming and/or tears. When she inevitably asks why you brought this up, you need to be ready with that list you made earlier. Your opinions are valid and important, so share them honestly.


Once you broach this subject with your beloved (or be-lusted, even), you need to listen to what she says. And I mean listen like you’ve never listened before. Let every thought that comes out of her mouth come to a complete conclusion before you even dream of responding.

I’m bringing the drama here because I simply cannot emphasize enough what a touchy, personal, and potentially deeply wounding topic fashion and grooming can be for women when approached insensitively.

We value your opinion. We want you to think we’re beautiful and attractive and worthy of love! If you plant the seed of doubt there, it can be hard to stop a weed from growing.

Alert! Alert! I’m not trying to scare you out of having this conversation, guys.

The hardest conversations are always the ones worth having if you ask me. Why? Because the things that are important to you are important. No question.

You don’t have to apologize for them, at all, and you shouldn’t feel like a jerk for caring. I care hugely about style and my appearance, and dating someone who didn’t really get that, like, at all, would be hard for me.

However, most of the guys I’ve dated have really appreciated my fashion acumen and gamely welcomed my advice and opinions. But for whatever reason, this situation doesn’t reverse all that well. Mars, Venus, all that.

So as you go along, be sincere. Stay positive and practice empathy. Hear her responses to your questions and navigate accordingly. If she seems put off? Table it and then consider how deeply this matters to you. It could very well be a deal-breaker for you, which is valid. People (including me) have broken up over much more trivial things.

If she’s interested and receptive to what you’re saying, keep going a bit. Perhaps you have a wedding or a special event coming up—what if you made an occasion out of getting ready together? Pour some cocktails, play music, take your time and again, lay the compliments on thick. Tell her what you like. (Editor’s note: This tactic works with all kinds of things.)

“Babe, I love when you do that thing with your hair.”

“That dress you wore to my cousin’s wedding looked so good on you. Do you still have it?”


Phew, that wasn’t so bad, was it? To wrap up, remember that couples will always have some imbalances no matter what—someone will always be more (or less!) “something” than the other person. We can’t be afraid to communicate about those differences, you guys! We can do this!

Taylor Davies splits her time between NYC and Sun Valley. She loves writing about menswear, overpriced martinis in dimly lit hotel bars, and cross-country skiing. Not necessarily in that order.