Nudging boyfriend towards fashionableness?

June 1, 2011 9:16 AM

How can I communicate to my boyfriend that I think he should make an effort to improve his appearance?

My boyfriend is hypersensitive about the way he looks, and reacts defensively to suggestions about clothes or other self-presentation suggestions. And, honestly, he does not have very good taste. It has always been thus, and I've always sort of gone back and forth on whether it's a big deal to me or not.

However, he came back from a job interview yesterday, and he was wearing the most gawdawful shirt ever. Shiny crayon blue artificial fabric grossness. I thought to myself, this is getting to the point of self-sabotage. Hopefully the interviewers were only considering his skills, abilities, and resume, but that's probably wishful thinking. This is an important job and it would help his career and if he got it I would be moving with him.

I want to talk to him about this, to maybe go shopping with him and help him pick out some new stuff, and just generally try to get him going in the direction of taking more pride in his appearance and making better choices. In the past, though, he's reacted very defensively to my comments. He claims a) Who am I to advise him? b) The choices he makes are fine and c) It shouldn't matter how he looks, what matters are his skills and personality and good inner qualities and all that. I think there's a d), though, behind all that: he thinks he's hopeless lookswise and doesn't even want to try.

Other things you might need to know:
-- We're a gay male couple in our late 20s, live together in Austin, been together almost 3 years.
-- I am not really fashionable myself and I hate shopping, but I like to look good and I'm also athletic, which I think helps (he's not).
-- We don't have a ton of money.
-- He has (has always had) the same pair of glasses that are just plain ugly. And while sometimes I don't care, there are times when I just resent him for not even trying. Maybe that's normal, maybe that's just a part of a long-term relationship, like the days when you can't stand that your boyfriend left dishes in the sink. But... it's something that I want to work on with him.

posted by fugitivefromchaingang to human relations (43 answers total)

My wife has solved this issue by just going ahead and buying me clothes. Granted, there are things she buys that I see, try on, and say "no way, I will never wear this in public", and we simply return them, no hard feelings either way. She's learned my tastes, and has helped me go from free t-shirts and jeans exclusively to actually asking her to buy me clothes for xmas/birthdays etc. So there's hope!
posted by Grither at 9:20 AM on June 1, 2011 [1 favorite]

I had some success with an ex-boyfriend on this once. He was pretty terribly dressed (again, as you say, to the point of self-sabotage), and after about 4 months of dating, I just started buying him clothes. it helped that I worked at the Gap and got a massive employee discount.

After continuously buying him clothes for every birthday, holiday, "congratulations it's wednesday!" and whatever other excuse I could come up with, he eventually took a look at the clothes I had bought him and thought "hmmmm, these clothes fit me and make me look good, my old ones do not" and explicitly told me to start dressing him. He eventually learned that he was a size S-M and not a size XL just because he was tall!

I would like to note the possibility for disaster: he decided after two years of this to become very interested in fashion on his own. So he went to mark's work warehouse and bought matching brown cargo pants, polo shirt, and engineer's cap and walked around looking literally like a turd for two weeks. we actually broke up shortly after.
posted by ameliaaah at 9:24 AM on June 1, 2011 [37 favorites]

Oh to add: on the "little money" front, I sympathize, and depending on where in the world/country/continent you are, savers/value vilage/goodwill/salvation army is definitely the way to go. i find it especially easy for men's clothes because there are fewer stupid trends that wind up flooding the racks six months later.
posted by ameliaaah at 9:26 AM on June 1, 2011 [3 favorites]

He's made it clear again and again that he does not want your feedback, so I think it's up to you to figure out whether or not this is a deal-breaker. There are worse things in life to be than poorly dressed. I had a boyfriend like that once; for whatever reason, he liked his old ratty clothes and had no interest in being made over. I think I once bought him some things for his birthday that he wore sometimes. How does your boyfriend respond if you buy him things?
posted by ThePinkSuperhero at 9:28 AM on June 1, 2011 [4 favorites]

In our early days as a couple, my husband dressed somewhat sloppily. I tried pointing it out to him and he'd get defensive. I started buying him some clothes on my own, usually I'd combine it with a shopping trip for myself so I could say, "Oh, saw this and I thought you'd like it" (rather than, "I can't stand how you dress so I went out shopping for you.") It was a bit of trial and error as to what stuff looked good on him, but in my opinion he slowly started to build a decent wardrobe, saw how good he could look, and now he's the one dressing himself in decent, flattering, non-sloppy ways.

We didn't have a lot of money either, so I bought stuff that was returnable in case it didn't look good or didn't fit. (A crazy clearance sale might be easy on the wallet, but if you can't return the stuff then you've wasted your money).

One thing I'd add is that going to an interview with a crazy shirt is something I'd gently bring up with him. Something like, "Job interviews tend to be conservative affairs, I think next time you should consider wearing X instead." He might get his back up, but he needs to hear it - and you might have planted a seed by mentioning it.
posted by DrGirlfriend at 9:32 AM on June 1, 2011 [3 favorites]

It shouldn't matter how he looks, what matters are his skills and personality and good inner qualities and all that.

Show him a couple of episodes of What Not To Wear. They've had a few man-makeovers on their show, though they're usually female. They're really good at explaining why your appearance matters in terms of the image you project, your own self-confidence and comfort, etc.
posted by litnerd at 9:34 AM on June 1, 2011

What about compliments? I've had a little bit of success with "that color is so great on you!" while leaving unspoken "but the fabric is terrible!" I also compliment lavishly and in detail anything that looks good. I talk about fashion stuff at random times...when we're chatting and goofing around on the internet, for example, so that there isn't any sense of "I'm looking at your terrible clothes and I want to fix them right now!"
posted by Frowner at 9:34 AM on June 1, 2011 [2 favorites]

He's said he doesn't want your help with his looks. If this is something that you can't live with, then you have to part ways with him...otherwise, butt-out and let baby bird crash on his own.
posted by inturnaround at 9:35 AM on June 1, 2011 [3 favorites]

I've approached this two ways with my partner of 7 years. First was constructive criticism, which worked not so well. The second was like previous posters, just buying him new clothes. Through theses experiences I found a couple of things:

1. My partners pathological hatred and/or indifference to clothing was largely related to body issues.

2. Buying him clothes that fit and flattered, and that were comfortable helped him "get" how dealing with clothes didn't have to be torture.

3. Make it super easy- lots of pants/shirts that work together. That way he doesn't have to learn fashion rules.

4. Once he started dressing better generally, I shut the fuck up when he occasionally wears something that I don't like. Now, I only voice my opinion in important situations (business meetings, important events).
posted by kimdog at 9:35 AM on June 1, 2011 [12 favorites]

He might not like your taste, especially if you're not fashionable. I tend to agree that you're not the best to be advising him. That doesn't mean that NO ONE should be advising him. Do you have a mutual friend whose style you both admire? Can that friend take him shopping?

My partner got a huge amount of help from platonic friends when he moved to NYC, including some really great hand-me-downs. I personally never comment on his clothes unless he's wearing something dirty, torn, or stained because that's just not my thing and while it might be helpful coming from someone who's really into men's fashion, it's a tad bit insulting coming from Ms. Yoga Pants, White Socks, and Dirty Tennis Shoes.
posted by the young rope-rider at 9:38 AM on June 1, 2011

Try working with praise rather than criticism. Don't tell him that he looks bad; tell him what you do like. Like instead of saying how gross his ugly shirt is, if he wears a nice shirt, you can tell him "you look really good in that shirt, you should get more like it" or stop into a frames store to check out the fashions and then "do you want to try this pair on, I think it would look great on you". You know, that kind of thing. (I've linked this article before on Ask: What Shamu Taught Me About a Happy Marriage)
posted by phoenixy at 9:38 AM on June 1, 2011 [4 favorites]

Are contact lenses a possibility? I had fairly unflattering glasses until I was 20, and wearing contacts regularly did amazing things for my physical self-esteem. It wasn't until then that I really took any pride in my appearance at all. Good taste didn't come right away, of course, but losing the wireframes I had worn since I was 6 was my first step towards giving a shit about how I looked. He might take better to a recommendation of contacts ("you'll have peripheral vision again!") than a more subjective suggestion like "wear this particular shirt."
posted by theodolite at 9:39 AM on June 1, 2011 [1 favorite]

from the opposite end of this situation? i like it when my boyfriend picks out my stuff.

i have decent taste on my own, but frankly, my color taste veers loud (as by loud i mean fuschia and safety orange is my favorite combination). boyfriend on the other hand, veers classic to neutral (everything he owns is, like, the color of a rock), and i used to be utterly tone deaf in that area.

when he started picking things out, it helped me figure out how to reconcile the two. so now i can deal with charcoal with a hint of fuschia. (conversely, i got him to buy himself an ice-blue sweater which looks devastating on him.)

i say buy him pretty things. don't ask, tell. but be positive to the point of chirpy about it. if he lashes out, gently point out that you are the one who has to look at him, and it's in his best interest to at least listen to your opinion.
posted by patricking at 9:43 AM on June 1, 2011 [2 favorites]

You might win him over more if you agreed with point c). It shouldn't matter. But point at the the world is not ideal, and that people are stupid and shallow, and that it does matter. Make him feel like he has an ally in this, he might be more willing to listen to adaptive strategies which are in his self-interest.
posted by stevis23 at 9:43 AM on June 1, 2011 [9 favorites]

There are lots of excellent answers already, but I feel like giving you a concise summary of how it seems to me:
buying good clothing for someone is helpful,
telling people that they have bad taste in clothing is not helpful.
posted by grizzled at 9:45 AM on June 1, 2011 [2 favorites]

This is an important job and it would help his career and if he got it I would be moving with him.

Is it getting to the point of self-sabotage, or is it getting to the point of sabotaging your plans?

He's an adult and he's made it clear he doesn't want you dressing him.
posted by headnsouth at 9:52 AM on June 1, 2011 [1 favorite]

I think this is sweet of you and nowhere near DTMFA territory...

Instead of showing him What Not to Wear, I'd try a similar exercise with him -- find out what he likes about the clothes he buys ( color, fit, superhero logo etc) and make subtle, more tasteful suggestions/purchases for him. Also, agree that if he doesn't like your taste you have to be more careful with suggestions.

Most people like my taste except my parents, who think I should basically dress in Lands End and J.Jill and braid my hair and this conversation with them all goes terribly.
posted by sweetkid at 10:04 AM on June 1, 2011

If you guys were more or less married, I'd say that you're allowed to help set boundaries for what your schmoopie wears out in public. There's stuff I have that I don't really care either way about, but biscotti says it makes me look like a ragamuffin that nobody loves, so I don't wear it outside the house. When I remember.

It's harder to say what's appropriate if you're the sorts of boyfriends who are still "just" boyfriends.
posted by ROU_Xenophobe at 10:06 AM on June 1, 2011

I have a tendency to wear stuff that I know looks terrible on me. I'll get something I think I like and then get it home, realize it looks pretty awful, and wear it anyway because I don't actually care all that much. A big part of the problem is that in my head, I'm still 18 and a competitive swimmer, and I have to be actively looking in the mirror to remember that I'm now 30 and sort of dumpy. (There's a whole host of gender issues here too, but as neither of you have boobs I won't go into them.)

My solution to this problem, in practical terms, has been to delegate someone to take me shopping when I buy new clothes. I try to pick a person who understands what I want to look like, I exercise occasional veto power (usually about colors,) and otherwise I buy what I'm told.

This person is not, and has never been, my partner. I think this is important - I can take "no, that makes your ass look weird" much, much better from a platonic friend than someone whom I desperately want to impress with my ass. So maybe he has a friend who can talk him into a shopping trip and guide him a bit?

I don't think buying him clothes is a bad idea (although that has backfired on friends of mine quite badly when they bought stuff for the body they thought I should have,) but a friendly joint shopping trip with the right platonic friend (someone with style, and ideally style not too dreadfully different from what your boy wants to have) might do the trick rather better.
posted by restless_nomad at 10:23 AM on June 1, 2011 [2 favorites]

I had this problem with my bf as well, and it stemmed largely from body image/cluelessness/no money issues. It made me feel a little shallow at first, but his raggedy, I'm-poor-and-I-don't-care-what-I-look-like ways were negatively affecting the way others saw him AND the way he saw himself.

The turning point was when he put on a t-shirt (yes, a plain Merona brand t-shirt) in a Target dressing room that FIT. I saw the spark in his eyes when he looked in the mirror and saw that he looked good (and he DID!). This event came 1.5 years after I began trying to nicely suggest that he purchase some new clothing; up to then, and even after that time, he was very defensive about this issue. (Point: it takes time to change.)

So, sometime when you're out at the mall or even a discount store with your sweetie, gently coax him into the fitting room with a handful (not too many or its overwhelming!) of cheap, simple items to try on. One look in the mirror with a properly-fitting item will do wonders.

Of course, I suppose this could also be performed at home, if you're willing to buy something, bring it home, then return if it doesn't work out.
posted by angab at 10:36 AM on June 1, 2011 [2 favorites]

I think it's entirely possible to say "hey, can I help you pick out what you wear to that job interview?" without making it an entire point about how the person dresses all the time. It seems to me that he doesn't really want your input about how he dresses all the time; I'm guessing you'll need to learn to make peace with that in your relationship. But it's totally possible to say something when there's a big lifechanging event at stake, like this interview (and hopefully future ones!)
posted by wyzewoman at 10:37 AM on June 1, 2011

Someone who "doesn't care about clothes" or thinks they "don't matter" shouldn't resist having you dress him, right? Because they don't matter, he may as well wear what you suggest.

I think maybe a response when it comes to jobs is: it shouldn't matter how he dresses, but employers are shallow--so try to meet their expectations. Don't let how you dress knock you out of contention. you can afford to turn down jobs because they'll work you too hard or pay too little, but you can't really "take a stand" against employers who judge you based on how you're dressed. I mean, is this the issue he's going to become an activist about?
posted by vitabellosi at 10:38 AM on June 1, 2011 [5 favorites]

nthing that praise works far better than criticism in cases like this. Also, if he doesn't want to go shopping, taking him on a shopping trip and then trying to foist your ideas of what he ought to wear on top of that will just guilt him into buying something that he will then keep in the back of his closet and never put on.

Instead, picking up a little gift and offering it can work wonders. It's not: "I hate that tie on you, you need to get a different one!" but, "I saw this tie in the store and thought of how it would bring out the blue in your eyes." And, since your budget is limited, small gifts work best. Combining the timing with meaningful dates--anniversaries, birthdays, etc--will make it feel less like nagging OR charity and thus less injurious to his pride.

Also, complimenting him in this way will help with (how sad it was to read this!) his feelings of not being attractive and the learned helplessness of 'what difference will it make, anyway'.

Glasses are important, btw, for function as well as form, and he may just not have the money to go to the eye doctor. So they're tougher, because if he had the lenses put in new frames, in the meantime, what would he wear to correct his vision? See if you can get a copy of his prescription yourself (most eye doctors will do this, no problem, and if you can't get it he should be able to) and maybe gift him another pair of glasses with frames you like, as a backup pair.
posted by misha at 10:40 AM on June 1, 2011 [1 favorite]

OK, first, do you dress well? I'd have to see what he has on first. You also say you don't dress well. It depends on your definition of shiny. It could be you have even worse choices for him.

So I suggest you get a third party's opinion.

then buy him clothes.
posted by Ironmouth at 10:47 AM on June 1, 2011 [1 favorite]

Buy him clothes. Ask him to wear clothes. Comment how sexy he looks in said clothes. Tear clothes off. Jump his bones.

Repeat as necessary.
posted by desjardins at 10:52 AM on June 1, 2011 [2 favorites]

What does your boyfriend like? Can you frame a makeover in the context of pampering himself? Or getting The Best Deal? Or owning High Quality Stuff That Will Last Forever? As opposed to "you have bad fashion sense, but thankfully I am here to help you."

Frankly, I'm using this tactic on myself, and it's working surprisingly well. For example, I like blogs a lot and will typically get interested in anything if there's a blog out there devoted to it. Because I want to get better at looking like a grown woman who actually wears outfits instead of a dingy tee shirt and that same old pair of jeans every day, I've added some wardrobe remix blogs to my google reader. I find this approach much easier than forcing myself to read fashion magazines or shop more or know about labels and such. For me it's about Learning Stuff about how to dress. Because if nothing else, I like Learning Stuff.
posted by Sara C. at 10:59 AM on June 1, 2011

Following on from what Sara C. said, it's a good idea to pick up some fashion magazines/catalogues/men's fitness mags (they generally have a fashion section) and leave them lying around your abode.

Most of the "ideas" in there may seem hideous and ghastly and completely unsuitable, but I usually pick up on a few "looks" I like. From there, you don't have to spend much to emulate those clothing choices.
posted by hnnrs at 11:06 AM on June 1, 2011

He claims a) Who am I to advise him?

"Somebody who is seen in public with you."

b) The choices he makes are fine

"We wouldn't be here if the choices you've made are fine. I'd like to help you, but I promise we're not having this talk for no reason."

c) It shouldn't matter how he looks, what matters are his skills and personality and good inner qualities and all that.

"People who don't take the time, or don't know how, to present themselves to the world are very clearly telegraphing what their real "inner qualities" are. I know I'm hardly one to talk, but I don't think you're sending the message you want to send here. Let's work on that together."

d) though, behind all that: he thinks he's hopeless lookswise and doesn't even want to try.

"I care about you, and I think you clean up pretty good, or I wouldn't be here. I know that I have this problem too, so let's both try to get better at this."
posted by mhoye at 11:10 AM on June 1, 2011 [2 favorites]

I agree with the others above who have suggested to buy clothes for him. The same goes for the eye glasses. If you make it really easy for him, you can probably get him to wear a new pair of eye glasses.

It sounds like he probably hasn't been to an eye doctor in ages. Sign him up for an eye doctor appointment and offer to provide the transportation to, and from, the doctor's office. If insurance doesn't cover the checkup fees, or if money is an issue, offer to chip in. If he resists, emphasize that eye health is important and it only takes up about an hour's worth of his time out of an entire year. Getting his eyes checked is very helpful in providing early detection for a number of illnesses that could impact his long term health.

After the checkup, the eye doctor will mostly likely hand him an eye glasses prescription, at this point, you can intercept your boyfriend and offer to help pick out some new frames. If he resists, you can comment on how blurry/scratched/chipped/bent/uncomfortable his current pair must be because they are so old, and reiterate that he will probably never have such a great opportunity to get new glasses for quite a while.

The goal is to make it easy for your boyfriend. He probably won't put up much resistance if he doesn't have to find an eye doctor, make the appointment, and find transportation to the doctor's office. Don't worry, he's not lazy, he probably has much more important things on his mind, like his next job interview. I'm sure he will recognize the effort you've put into getting him an eye appointment, and he'll thank you.

Good luck.
posted by nikkorizz at 11:14 AM on June 1, 2011

If this was my boyfriend, I'd round up all his friends and have an intervention on the topic, for serious.

This is possibly why I have been dumped a lot however.
posted by RJ Reynolds at 11:28 AM on June 1, 2011 [3 favorites]

Was the job interview for an IT or software position? If so, be aware that, in some geek hierarchies, points are deducted for dressing nicely - because you're asking to be judged not on your technical skills, but on your social slickness. Here's some support for this argument:

http://www.codethinked.com/the-programmer-dress-code
http://www.theregister.co.uk/2005/10/25/otto_clothes

or google Sergey Brin, Larry Page, Mark Zuckerburg, etc.

as for the shiny, crayon blue artificial fabric... I can't condemn it on that description alone. You and I may prefer cotton, but rayon's in, in some circles.
posted by at at 11:30 AM on June 1, 2011

Make a consistent effort to describe his good fashion choices (he must make a good choice every so often, right?) as sexually appealing. It'll take a while, but it'll eventually make its way into his fashion-choosing algorithms, with less conflict and bad feelings than by criticizing his bad choices.

It worked on me.
posted by Salvor Hardin at 11:33 AM on June 1, 2011

I want to talk to him about this, to maybe go shopping with him and help him pick out some new stuff, and just generally try to get him going in the direction of taking more pride in his appearance and making better choices. In the past, though, he's reacted very defensively to my comments

How are you talking to him about it? The tone you're using in your AskMe is really negative. If you're phrasing things negatively, then of COURSE he's going to be defensive about it. "You should take more pride in your appearance" and "You don't make very good choices when it comes to clothes" are insults. If the only way you can talk about this is negatively, he's going to fight you every single step of the way.
posted by 23skidoo at 11:47 AM on June 1, 2011 [1 favorite]

"He claims a) Who am I to advise him? b) The choices he makes are fine and c) It shouldn't matter how he looks, what matters are his skills and personality and good inner qualities and all that. I think there's a d), though, behind all that: he thinks he's hopeless lookswise and doesn't even want to try."

I am on the "push on through the resistance" squad on this one. My now-husband was a terrible dresser when we met, coming out of college and having not really shopped in four years. I swear he owned no pants that were not high-water. His attitude was much the same as your boyf's (though not so much with a) plus some e) if you are criticizing my clothes, you must not find me attractive and f) fashion is lame and stupid and I will look like a jerk.

I insisted, over and over, that he WAS attractive and he could dress better to highlight that, that whether or not it's fair people do judge by your clothes, and that he didn't have to be a fashion plate, that I bet we could find something he liked that ALSO fit right and looked good. It took a while but I convinced him to let me take him shopping.

And then I introduced him to cargo pants.

And then I won. :) He was really excited by the idea of comfortable pants with 8 million pockets.

Anyway, I started with one particular arena of clothing -- in his case, mostly business casual (other than the cargo pants), since he barely owned any business casual. As he saw that he actually did look better and was more comfortable and more confident, AND that we could find things that suited his personal taste, he gave ground on other areas and began to weed through the old clothes, and trust my taste, and develop his own taste.

Another line you can take, especially with the glasses, is that things look "dated" instead of ugly. And really that's the problem with glasses half the time anyway; my husband's glasses 10 years ago, which looked fine at the time, now look laughably dated in pictures. You might also try to find a non-threatening friend to go shopping with him or both of you, since you admit your taste is sketchy. Maybe a female friend, women can often give fashion feedback in a more gentle way and since women are "supposed" to be good at fashion, it might not feel as personal.

Sometimes you have to be the one to point out something like this to your partner, and it's as painful for you as it is for them. But the only person who's going to tell you that you dress like a street person, or you smell like a wet dog, or your bra is hanging out in embarrassing fashion, or that shade of red makes you look like you're in the last stages of some form of 18th-century consumption is your partner. And I totally flare up at my husband and get upset when he points out my outfit has gone awry in some fashion, but I also know he's the only person that would do that and it saves me a lot of embarrassment. A large part of it is that I'm embarrassed that HE noticed ... shouldn't he just be noticing how perfect I am, all the time? So that's part of what your boyf is feeling, even if underneath it he knows that you're the only one who'll tell him what he needs to hear and is grateful.

Anyway, if you opt for "push on through the resistance," focus on the fact that YOU find him attractive but the world is judgy, and then focus on finding him things that are comfortable and attractive AND suit his personal style. Most people are pretty happy when they're comfortable, attractive, AND expressing their personal style. Get him a couple doses of that drug and he'll be more on board. :)
posted by Eyebrows McGee at 11:48 AM on June 1, 2011 [2 favorites]

Remember that you are probably the number one influence on him. If you start dressing noticeable nicer, he will probably follow suit.

You mentioned that you're not very fashionable yourself, so in his opinion you have no right to tell him what's fashionable to wear. He's not fashionable inclined, so he probably can't tell the difference between the level of offensiveness between his wardrobe and your wardrobe. To him, they are probably equal in fashion-ness. However, in YOUR opinion, you disagree. You feel that he dresses worse than you.

You may, or may not, dress better than him, I don't know, but he can probably recognize that you aren't too fashionable yourself. This is why you come off as a hypocrite for telling him how to dress.

If you can admit to him that your own fashion style sucks, then it won't be as hard for him to admit that his sucks too. You'll come off as less offensive if you can convince him that BOTH of you need new clothing and and BOTH of you need to go shopping for new clothes. By making it a group activity, he won't feel singled out, and he will feel like you made a more justified opinion.
posted by nikkorizz at 11:51 AM on June 1, 2011

if he is "hypersensitive" about this issue, I am SURE he is damn well aware of what he is wearing, in spite of your differing opinion -- attempts to change or pressure him will only increase his defensiveness (however small, however justified) - even if those attempts seem successful to you.
posted by mrmarley at 11:54 AM on June 1, 2011 [1 favorite]

I can get my boyfriend of five years to clean up nicely for weddings and Christmas parties, but most of the time, his wardrobe consists of jeans and t-shirts his mom buys him from the sale rack at Old Navy. He is also prone to wearing his sneakers until they practically rot off his feet. Make no mistake: there is nothing stylish or trendy about him. Thankfully, he works in a kitchen, so his work clothes are predetermined.

He's pretty amenable to me buying him clothes and he'll wear things I get him, but I don't do this very often. Why not? Because I realized a long time ago that he is who he is and everybody around him absolutely loves him and accepts him for who he is. Having nice clothes is not important to him. I'm not saying it's wrong to encourage your SO to look nice, but were I to put on an episode of What Not To Wear or offer to take him shopping, he would just give me that amused grin of his and shake his head. Still, we've made definite progress over the years. It's been years since I've uttered the phrase "Are you honestly leaving the house wearing THAT?!?!?!?" ("That" could have been a number of things, an ugly ill-fitting tank top, white Toronto Maple Leafs socks with shorts, etc).

Besides, if he were to tell me he didn't like my clothes, I'd probably be pretty bummed.
posted by futureisunwritten at 12:04 PM on June 1, 2011

From litnerd: Show him a couple of episodes of What Not To Wear.

Why not go further and just nominate him for the show? Seriously! He sounds like a perfect candidate and someone who could definitely use Stacey and Clinton's help. Be sure to let us know if he ever gets on the show!!
posted by foxjacket at 12:51 PM on June 1, 2011

I'm a woman, but I've been in your boyfriend's position. I resisted change for some of the reasons already mentioned above, but I wanted to say that the money may be a bigger deal than you think. When my boyfriend made suggestions about my clothing, it would piss me off that he didn't seem to be considering reality. It felt like he was saying, "I'm dissatisfied with this aspect of you, and I think you should address it by purchasing X and Y, even though I'm fully aware that we don't have the budget to do so!" So maybe there are things you could do to ease that pressure. Help him work some new clothes into your budget. A related issue is that I've always felt irrationally guilty for spending "unnecessary" money on myself, so you could consider that angle too. A little encouragement that your boyfriend is worth the cost (and that the cost doesn't have to be exorbitant) could go a long way.
posted by spinto at 1:22 PM on June 1, 2011

I am not really fashionable myself and I hate shopping, but I like to look good and I'm also athletic, which I think helps (he's not).

I am not a gay man, but I am a woman who is no stranger to issues of body image playing out in weird ways in relationships, and I think your sentence above is the crux of the issue here.

You seem to be suggesting that you feel your body type is objectively more attractive than your boyfriend's and that clothes therefore look better on you, so you don't have to expend the same effort that you're suggesting for him. He, no doubt, has perceived that you feel this way. So when you tell him that his clothes don't look good, I bet you that he's hearing "Your body doesn't look good, so at least put some better clothes on it so that you look more or less OK." I think you should ask yourself whether this is, in fact, what you mean. How you handle your situation might depend on the answer.
posted by zadermatermorts at 2:04 PM on June 1, 2011 [6 favorites]

"What Not To Wear" will not work on people who are defensive. They have to be at least a little open to the idea of change first.

I say this as a person who, though she could probably use the help, would have no hesitation at permanently dumping any relationship with a person who dared do a single thing even remotely like what they do on that show. Even if they were my favorite person and had never done anything wrong before and offered chocolate and solid bars of gold in penance after realizing how brutally they had screwed up.

I recommend buying stuff as gifts - and the positive reinforcement thing. But this is a ridiculously lame hill to die on. Save the nuclear weapons for something that actually impacts you in a tangible way.

Well, okay, if they gave me lots of gold I might forgive them. But it'd still be a "you don't ever, ever do this, or bring it up ever again" thing.
posted by SMPA at 2:43 PM on June 1, 2011 [2 favorites]

The answer currently marked best sums it up well.

"What Not to Wear" is probably not suitable for someone with his mindset and could actually actively alienate him from the goal.

We have loads of great thrift/consignment/vintage shops here in Austin. Thrift will be more reliably to your taste financially, but you can find deals at consignment/vintage, too (accessories are a good bet here, especially). For modern/new things, try Ross or Burlington Coat Factory. Every store has a different mix/volume, so try a couple of each.

I wish you happy shopping & a receptive fella!
posted by batmonkey at 11:49 PM on June 1, 2011

Have you considered that maybe he doesn't agree with what you think looks good?

Certainly, people have been telling me to dress fashionably for many years now. I refuse. It looks ugly on the hangar, and worse on me. Since I'm the one wearing it, I get the first, last, and only say. Sure, I could stand to scrub up a little once in a while - but certainly not in the direction of fashionable clothing, ick. I'll stick to my jeans and tshirts, thanks.

Instead of saying 'that looks awful', perhaps consider encouraging him to think about his personal aesthetic. What styles appeal to him (even if he'd never wear them)? What would he like to be able to wear, if he thought he was good enough? What does he think of what you wear?

For the glasses - new glasses frames are bloody scary, if your eyes are bad enough so you can't really see well when trying on frames. It's a huge decision. Again, be positive. Don't say 'those are ugly, why the hell do you keep them?', try 'I reckon this style would look really cute on you'. Sometime when you're near the shops and have a good camera on you, make it a fun thing to go into an eyewear shop and try on every frame in the place, taking photos of each. Have fun with it.

Being positive is the key. And be aware, especially if it's connected to self-confidence issues, it can take years. Case in point; I've only just learned how to use mascara, and I just turned 30. It's taken me this long to work up the bravery to be that feminine.
posted by ysabet at 5:05 AM on June 2, 2011