One Couple Explains: How To Train Your Boyfriend To Dress Well

by Mike Barthel

Rachel and Mike met at a pretentious art-rock university in the Midwest when they were both 21. They moved to New York after graduating (Rachel two years later, due to a post-college year abroad), went to grad school upstate, and are now living a cross-country relationship (New York-Seattle) that’s nine years old. In this discussion Rachel reveals how she saved Mike from a life of fashion tragedy.

Mike: So! Let’s talk about CLOTHES.
I wrote a piece where I gave strategies for getting boys to dress nicer.
And really it was just what you did with me, yes?

Rachel: Pretty much, yes.
I like clothes! People look better with certain clothes on than they do with other kinds of clothes on. So we can get all self loathing or we can buy clothes!
Also, I am the short fat sister so my mom would always buy me clothes because she wanted me to feel pretty.
It worked swimmingly! Thanks mom!

Mike: Being a straight boy, I was basically dressed by my mother. I did dress myself when I did my SEMESTER in LONDON. (Because I went to a LIBERAL ARTS SCHOOL.)
I went to Topshop and had gray microfiber pants and went clubbing like twice.
I also went to Camden market and bought secondhand things that made me look like a Scottish file clerk from 1974.
I also bought a lot of secondhand things.
I thought it was still the 90s!

Rachel: You got that Pulp T-shirt, too.

Mike: That is the only band t-shirt I still have!
You made me throw out the Metallica shirt that was two sizes too small.

Rachel: That Metallica shirt was waaaaay too small. Did it ever fit you?

Mike: Well I still had it because it looked so pristine, because I never wore it!
I guess I thought, you know, eventually I would become much smaller somehow?
I mean I did, sorta, in the two years I spent in New York while you were finishing college.
Let’s talk about that!
I was in an electroclash band!

Rachel: Fuck, you leave for NYC and I come and visit you and after like 6 months you are in fucking black skinny jeans!
BLACK SKINNY JEANS!

Mike: The lead singer took me to Trash and Vaudeville!
And that dude who looks like he’s the bassist in Cinderella told me I looked good in them!

Rachel: He was lying.

Mike: I mean, left to my own devices my fashion sense is to wear the shiniest thing possible.
Ideally it would be blinking or on fire.

Rachel: That is not true. That would be too much work.
Left to your own devices you would wear your blue robe that you have had for a decade, and maybe a pair of stretched-out boxer briefs.

Mike: True.
I mean, I popped the button on the skinny jeans after like a month.
There is only so much weight you can lose from crushing depression.
So OK, how did you break me out of dressing like this?

Rachel: Well the jeans took care of themselves.

Mike: I will kill you.

Rachel: You respond well to praise.

Mike: I do!

Rachel: And you assume I am always right about aesthetic issues.

Mike: You are!

Rachel: So one day you were looking for a t-shirt for work the next day because we had not done laundry in months.
And we were at the K-Mart by Astor Place to get you a pack of white Hanes t-shirts.
We were looking for a t-shirt and I suggested that you buy a polo shirt because that would make your shoulders look broader than the stretched-out, oversized shirts you normally wore.

Mike: And I was like, “Wow, a polo shirt! I’d never thought of wearing that!”

Rachel: What is wrong with you?
No really, did your mom never bring home a polo from JC Penney?

Mike: I think she was just happy I wasn’t wearing trash bags at a certain point.
She did what she could, the poor woman.
It’s not easy working with me, you know?

Rachel: Well it was for me, because you assumed I knew what I was talking about.

Mike: You had large sunglasses and large earrings!

Rachel: So we started moving you away from just ironic Ts.

Mike: Yes
I bought more polo shirts!
Well, after a few months.
You introduced me to this idea of “buying things from the Gap.”
It was amazing!
So many clothes to buy!
Fewer ironic slogans, but still!
Did this new look work for me?

Rachel: Yes, but apparently too well, when we went to visit my parents in Indiana you were gay bashed and left with a broken nose.

Next: Yes, it’s true-but the gay-bashing fixed the jeans problem!

Mike: You see?
Some boys think polo shirts are gay!

Rachel: Which actually took care of the ugliest of your jeans due to the blood stains.

Mike: THE PERFECT PLAN.
You got me to buy a polo, which got me gay-bashed, which got me to get rid of my ugly jeans!

Rachel: Yes, it was all a nefarious plot.
So then the next big development was when we went to visit my parents for Passover.
And like I said above I am the short fat sister, so even though I have a job and live in NYC, my mom gave me her credit card to go shopping at the mall.
And we found these really great Banana Republic slim cut wool pants that were on super sale.
I think these were the first lined pants you ever owned. I remember the lining confusing you.

Mike: I didn’t even realize that my previous pants looked awful.
I bought my pants way too short!
Because if they were too long they would get caught under my shoes and would get ragged and so of course the only way to deal with that was to buy pants that were too short for me.
Not, you know, get a better belt.
God, this is turning into a “What Not To Wear” episode.

Rachel: Okay, so you wore pleated baggy pants that were too short for you.
YUM.

Mike: I had learned how to dress in the 90s!
You wore “relaxed” things!

Rachel: I did not wear relaxed things.
I wear shit that fits.
Wearing relaxed things is not awesome. Awesome is wearing clothes that fit.

Mike: Oh girl, I’ve seen pictures of you in a plaid shirt with Doc Martins.

Rachel: It was the 90s, I was 15 or 16, and I looked AMAZING!

Mike: I think the problem with straight boys (and lesbians?) is that they think that the way they dress when they are 15 or 16 is the only authentic way to dress.

Rachel: I think people who are uncomfortable with the idea of clothes think that fashion is idiotic and vapid, and that people should love them for being who they are.
FUCK THAT.
I am not your mother.
I was not looking for a boy to love for who he was.
I was looking for an accessory!
Now I love you and all, but really, I wanted boys to look good on my arm when I was dating.

Mike: Does that make me a boy toy?

Rachel: Well, you know, we were 21…

Mike: DOES THAT MAKE ME A BOY TOY I SAID.

Rachel: I am sorry, of course it does you sexy piece of man meat.

Mike: Thank you.

Rachel: Okay, so we bought you a pair of pants that fit you!

Mike: Pants and a shirt!
Almost an outfit!

Rachel: At a certain point I realized I had overlooked the possibility of button down shirts, because I was tricked into thinking you had some already.

Mike: I did have some!

Rachel: But they were all way too small, and polyester.

Mike: I didn’t know there were different fabrics?

Rachel: You complain about sweating and humidity in the summer in NYC and then fucking walked around basically wrapped in plastic!

Mike: So yes, here are the things I did not know:
1) there are different fabrics.
2) different clothes look differently on you.
3) you can just wear a tighter belt.
Now how did you get me to make the leap from being able to buy better pieces to being able to have some sort of overall style?
We kinda figured out my color scheme, didn’t we?

Rachel: Yes it actually started with maybe your second polo shirt. It was this kind of bright orange.

Mike: I still have that!

Rachel: We learned that you are what my mom would call A FALL.

Mike: So I dressed in warm earth tones and we moved on from there.
I guess it came down to that I wanted to dress well but really didn’t know how.
And I didn’t just need to be given the knowledge to be able to do that, though I definitely needed that.
I also needed to be led to it in a way that I would accept.
I think people trying to dress dudes well would like to hear your secrets.

Rachel: Tell him he looks hot whenever he wears something you kind-of, sort-of like, or something that is along the lines of what you would like to see him in.
Also, SUPER SALES.
That’s a big secret.

Mike: Yes.
Because then he can’t be like “why would I spend all this money on something stupid like clothes?”

Rachel: He is not going to go from his mother bringing him home a pair of Levis to spending a couple hundred bucks on pants.
So go with super sales.
He has to see why the more expensive clothes are worth buying before he spends any real money on them.
Which is a Catch-22!

Mike: So ladies need to develop their own style eye for men’s clothes.
So they can find cheap clothes that also have the right cut.
Also you have spoken about the role of FUN?

Rachel: Playing dress up!
We have alter egos such as Bud and Linda-they are a trashy 40-something couple, and we go to Wal-Mart and get American eagle t-shirts and cut them up and go to the motor speedway.
Then when we went to Saratoga, we got dressed up in all-white outfits to see the ponies.
Frame it as getting dressed up in the proper costume.

Mike: So although you are normally quite pro-shame when it comes to personal improvement, you can’t lead with shame in this instance.
You need to make it seem exciting.

Rachel: Exactly.
I am a girl, so I know that shaming people about what they look like just backfires.
It sends them deeper into jeans/t-shirt/hoodie world.
You have to make them believe that clothes are fun!
So the original post that you were responding to about that told girls to ask their men to dress better is actually terrible advice.

Mike: Yes!

Rachel: I mean I would be really hurt if you came up to me and said, “Honey, I really need you to dress better.”
I would be ashamed and just want to hide.

Mike: Oh no!

Rachel: And why wouldn’t men feel the same way?
They don’t want to hear, “Honey, you look like shit.”
Men don’t care about clothes, but they do care about the way they look. They just don’t get that those are one in the same.

Mike: Well I think we are done here!
Do you have any further thoughts?

Rachel: No, I like the way you dress now. You are super dreamy.

Mike: Thank you!
You still look like a whore.

Rachel: Fuck you.

Mike Barthel is the luckiest man in the world.