Does the hat make the man?
July 10, 2012 5:14 PM   Subscribe

I started dating a guy who is great but his fashion sense is ruining my buzz. Ill fitting clothes, sort of a "Scarface" aesthetic, age-inappropriate hats--you name it. And I haven't even gotten to shoes that I can only describe as . . . puzzling and vaguely medieval. What should I do with this?

Both of us are in our mid-30s and have been dating on and off for four months. We're respectively financially comfortable and professionally accomplished. I have a job that requires me to show up to work "dressed," and I think I have pretty good taste and make the appropriate personal and professional efforts. He works at home and can generally be found in shorts and a t-shirt. I have no problem with that. It's when he gets "dressed" to go out that he runs off the rails. It's to the point that I don't want to invite him to work functions/receptions for fear of what he'll wear.

I have no doubt that I'll immediately be jumped on for being shallow, because in many respects this guy is great, but I'm willing to take the risk. I'm not looking for GQ--I'm just looking for sport coats that don't billow and that don't look like they are from the 1980s, jeans that fit, shirts not made out of shiny materials. Can you help me figure out if I should even approach this? How can I provide gentle feedback/guidance about this? Or even can I? It's too early to buy him clothes, as I've seen suggested in other answers here, and he gives no indication that he is unhappy with his wardrobe. Asking anonymously because he knows how much I love the Green. Thanks, Mefites! Don't judge me too harshly!
posted by anonymous to Human Relations (48 answers total) 5 users marked this as a favorite
I don't see how you can do this, without offending him and/or having the impact of getting him to be more aesthetically appealing, if he is happy with how he looks. Especially if you've only been dating on-and-off for a few months.
posted by sm1tten at 5:19 PM on July 10, 2012 [3 favorites]

I don't think you're vain. Who you're with reflects you indirectly. However, approaching this is tricky. Perhaps bring up something about your work functions requiring a more "conservative" approach.
posted by DoubleLune at 5:23 PM on July 10, 2012

Hmmm, I don't see how you can provide fashion guidance so early in a relationship. Learn to let it go, and invite him to functions attended by people who aren't Anna Wintour or her acolytes. It doesn't reflect on you, and depending on who you socialize with, they should see it as only an amusing quirk, not a character defect.
posted by computech_apolloniajames at 5:25 PM on July 10, 2012 [1 favorite]

If being a good (or just not embarassing) dresser is really important to you in a man, maybe that's enough to stop seeing him. BUT, if this guy is great otherwise, isn't this maybe something you can just accept? Unless he mentions being hopeless fashion-wise to open it up for you to suggest some changes, I don't really think you can say anything. I've had exes that were not awesome dressers (think Ed Hardy) and you just have to laugh it off in social situations. No one is judging you by what your boyfriend wears, and if someone is, they are shallow and not worth your thoughts.
posted by heavenstobetsy at 5:25 PM on July 10, 2012 [4 favorites]

I agree, unless he himself doesn't like his scarface aesthetic, then the best you can do is buy him an outfit as a gift and see if he prefers your sense of style for him-- but don't push it!

As a person who hates shopping, I would totally appreciate that sort of thing. If I liked the way I looked in the gifted clothes that is. . .
posted by abirdinthehand at 5:25 PM on July 10, 2012 [2 favorites]

he gives no indication that he is unhappy with his wardrobe.

You can't "provide gentle feedback/guidance" to someone who hasn't asked for it and arguably doesn't need it (he's not gambling away his pension here).

It's to the point that I don't want to invite him to work functions/receptions for fear of what he'll wear.

Tell him this. It's worth an honest conversation, at least.

I have a job that requires me to show up to work "dressed," and I think I have pretty good taste and make the appropriate personal and professional efforts.

One person's "dressed appropriately for work" is another person's "corporate uniform devoid of creativity or interest."
posted by headnsouth at 5:27 PM on July 10, 2012 [8 favorites]

How does this guy feel about spending money? In my experience, the "shiny shirt + fedora = eveningwear" problem is compounded by excessive thrift.

I suggest you take him shopping, as a fun activity, that leads into "here, try these on...". I had some success doing this with a very close male friend. Go to the mall and make an afternoon of it--shop for the both of you. Stores like Gap that have men's and women's clothes are a good place to start.

Also, I suggest a triage approach. What is the most alarming wardrobe problem? Work on one thing at a time. Like pants. It is totally possible to get a fashion-averse guy to wear better pants. It will require some patience, and compromise on both parts. But I don't think you are shallow for wanting him to dress in a way that reflects his professional status and nice personality. (I mean, that's the whole point of shows like "What Not To Wear" targeted at women.)
posted by Tesseractive at 5:28 PM on July 10, 2012 [2 favorites]

As a guy in his early thirties, this can be tricky territory. He may simply enjoy his look... or he just doesn't realize how other people are perceiving him. It's just like level of cleanliness, yours is higher than his. Unfortunately, you're not going to just be able to change him. And if you do, he may end up feeling resentful towards you.

Best bet? Accompany him the next time he goes shopping and suggest some things. Try buying him something very close to what he normally wears but just kicked up a notch. Then, shower him with compliments when he wears it... tell him how good he looks. Jump his bones. Positive reinforcement. Take him out somewhere... tell him you're jealous of the attention he's getting. Basically, you need to get him to come to the conclusion on his own that he can look better with a little more effort. If you push, you'll get the opposite effect.
posted by miasma at 5:30 PM on July 10, 2012 [3 favorites]

You know, he probably organized his job and life around the fact that it gives him freedom to dress as he pleases.

However, you should simply ask him if he has anything to wear to work functions/receptions. It's perfectly likely that he knows how to dress appropriately for formal occasions, just that he chooses not to dress like that if he doesn't have to.
posted by deanc at 5:34 PM on July 10, 2012 [5 favorites]

I don't think you're shallow. You shouldn't tell him what to wear - that's controlling - but work functions absolutely require a certain level of dress for you and your date. I'm not into men telling women what to wear, but I absolutely wouldn't think twice about a guy not wanting his wife to show up at his job in a tube top and cutoffs.

When the next work function comes up and you want to invite him, tell him as soon as you invite him that it's semi-formal or whatever - e.g., "Hey, my company's hosting a dinner at ---. The dress is business casual - slacks, sports jacket, etc. You want to come?"

This way you've been up front with the dress code and if he agrees to that and still dresses oddly, then it's also a matter of him essentially breaking the "agreement" or hey, he might get the hint and dress completely "normally". I have to admit I tend to be clueless about many functions - overdressing or underdressing for many things. It might actually help for you to give him guidelines for functions.

It's not like you're telling him what to wear all the time.
posted by Lt. Bunny Wigglesworth at 5:37 PM on July 10, 2012 [16 favorites]

I'm surprised he is willing to go to work functions after such a short time together. Nice guy! If it is important to you that he accompany you to work stuff, I would say something like, "I hate to do this, man, but could you possibly go the Dockers and button-down route for this barbecue? Or if you want to stay home, that's cool, too." As for the rest of the time...well...
posted by skbw at 5:39 PM on July 10, 2012 [1 favorite]

Suggesting things that you like on him while not saying anything about the clothes you don't like is probably the safest bet here. So if he has a shirt you do like, make some comments about it, but don't say much about anything else. That way you don't hurt his feelings and you're getting your message across.

Something that also can help is going to the tailor together. I've done it in the past with my SOs, and it's always a confidence boost to have a shirt that you like look even better with proper fit. It's very hard to understand this until you get something tailored. Additionally, depending on where you live, getting a men's shirt shirt taken in doesn't cost an arm and a leg.
posted by neveroddoreven at 5:47 PM on July 10, 2012

I think you should talk to him about this. I can't say he won't care, but there is a chance he won't.

I know there's a lot of relationship advise in Metafilter that says, "You can't change people. You shouldn't try to."

I think that this is true, but also a little glib. You can't change something that is fundamental to a person and which they care about. But not everyone cares about everything.

Using myself as an example, there is a lot about myself I don't really give a damn about. I once had a girlfriend tell me that she really didn't like under arm hair on me. I had never shaved my underarms, but it wasn't any statement about how I felt. I never shaved because it never occurred to me and I never had a reason to. For the rest of the time we went out I shaved my underarms because I didn't give a damn; she did give a damn, and so her desires won out. For other women I've changed deodorant I wore, or shampoo I used, I've bought different pillows, and many other things they cared about and I didn't.

In the same vein women have told me they didn't particularly care for certain shirts, shoes, etc... that I wore and I stopped. Because, really, I don't care one bit. A complete style change I would probably be a deal breaker. But asking me to dress a certain way some of the time, especially when it's to confirm to a social convention? No problem.

I'm sitting here, right now, wearing a suit, tie, and glasses and my hair is cut far more conservatively than I would really like. Why? Because as a lawyer I'm expected to dress that way sometimes. No other reason. It's not a deep part of me and if tomorrow lawyers were expected to wear robes, wigs, and red clown noses I'd put them on.

At the same time I have a statute of a big Iron Frog I like to have up on my wall. Any girl who wanted me to take that down would have a problem. Why? Because I do like it, I do care about it. Just happens to be that way.

So, what I'm saying, before working yourself up about this ask him. Does he care about this. If not, tell him you do and you'd appreciate if he wore X, Y, and Z for these occasions because it would make you more comfortable and, potentially, help your career. He might not give a damn.

On the same side, be fair about it. If he wants you to change something you don't care about, change it. To yourself be true, sure, but not everything is fundamental to people's sense of self.
posted by bswinburn at 5:50 PM on July 10, 2012 [40 favorites]

"under arm hair on men", me too, of course, but I was just a member of that class.
posted by bswinburn at 5:54 PM on July 10, 2012

Gently nudge him towards The Art of Manliness. Chances are that if you've noticed how he dresses, other people do to.
posted by ikaruga at 5:58 PM on July 10, 2012

Your question first made me think that he was being disrespectful with how he dressed, but then you said he actually did wear a sport-coat. So really your problem seems to be his sense of style doesn't jive with your own.

From a guy's point of view: each woman has a different sense of style for "her man". You can go from dating the woman who likes skinny jeans and corduroy coats to one that likes a $200 pair of Luckys and polo shirts. My point is that being told what to wear without being able to just be yourself is annoying. If his dressing embarrasses you then I wouldn't invite him until your relationship is at a point where you feel you can discuss clothing with him. But make sure he is the one deciding, not you.
posted by zombieApoc at 6:02 PM on July 10, 2012

There's a viable approach to this, I think. Couch it in positive terms ("things can be better") rather than negative ("things are bad"), identify the issue as something external to him (clothes) and not inherent to him (fashion sense), and respect that it's his decision and not something you can or should demand.

Something like this, said with an affectionate tone: "Hey boyfriend, I was thinking something earlier today and wanted to run it by you. I find you really attractive, although sometimes when we go out I feel your clothes are holding you back. Would adding an outfit or two to your wardrobe be something you'd be interested in? I'd love to help you shop, if you'd like."

And then accept whatever his answer is. He may be a bit stung, even by that, it's true; especially if he has actually put thought into his wardrobe and likes it. But, to my mind, it's better than the alternative: His partner being displeased by something but not comfortable enough to address it directly.
posted by kprincehouse at 6:07 PM on July 10, 2012

i'm with bswinburn on this one. there are lots of really nice ways of telling him that there's a de facto dress code in place in your professional milieu and it would make you happy if he wouldn't mind adhering to it. it doesn't have to be a negative, at all - i.e. you don't have to include the suggestion that he's a slob, or that there's something wrong with him. he'll go along with it. at that point, if you want to use a little positive reinforcement, just go subtle and casual - just look at his clothes and smile, or tell him once that he looks nice. i think the key is to never let on that this bothers you, or is a "problem." guys, like everyone else, hate feeling like a problem, but they enjoy pleasing people they like.
posted by facetious at 6:10 PM on July 10, 2012 [1 favorite]

This guy is obviously oblivious, and there's a good chance he would welcome help. Most guys I know are aware they are hopeless dressers and are always asking women for help. Start small, with a "I know you like that hat, but it really doesn't work" and build your way up to a wardrobe shift. If he can't handle this, move on, who cares. Being embarrassed to go out with someone who dresses like this means you are normal.
posted by Patbon at 6:18 PM on July 10, 2012 [1 favorite]

left-field suggestion: do you have a Pinterest account? If you do, you might curate a board of dapper men's clothing (along with your various other boards featuring a different range of interests) and casually show him your collection the next time you're hanging out together.

Also, you might try pinning the price and website/store of each item if you think that cost and/or availability could make any difference in influencing his fashion choices.

But I caution you that if you do this, make sure whatever you're doing is CONSISTENT. Don't make ONE board of dude's clothes with prices attached and force him to look at it, obviously; make one for yourself, too - you could even try asking him what he thinks of your "fantasy style board" first for feedback. I mean, for all you know, maybe he hates what you wear sometimes, too.

Done correctly, this could be mutually beneficial and advance your relationship. Done poorly, well... there's always more people to date.
posted by Unicorn on the cob at 6:19 PM on July 10, 2012 [1 favorite]

Is he into his weird little personal aesthetic, or is it maybe just that he never shops, has no idea how to shop, and takes the approach that if it physically goes on his body and doesn't show off any inappropriate parts, it's functional clothing and perfectly fine to keep wearing?

Maybe he just needs some influences. I like the idea of Art of Manliness, as well as Put This On.

Also, maybe frame it as wanting to play dress-up? Or stage a shopping trip where you ask him to come along shopping for yourself, and get him to try on the kinds of things you think he should be wearing?

Again, all this assumes that he'd be open to change/new stuff, but is just clueless or doesn't much care.

If he's in love with his ill-fitting jackets and unfortunate shoes, I don't know what to tell you.
posted by Sara C. at 6:22 PM on July 10, 2012 [2 favorites]

I think it is fine if you gently ask to take him shopping, and pick out a few outfits for him. Most guys have no idea how to dress. We are vaguely aware of the fact and would like to dress better but have no idea where to begin.
posted by LarryC at 6:42 PM on July 10, 2012

I dated someone who showed up at my door wearing every item in the exact same shade of brown. He looked like a human poo. It was all old and ratty as well.

I'm not a fashion diva, and used to have no issue going out in a bathrobe (undergrad) and sweats, but I have realized just how much our appearance precedes our personality when it comes to how others view us. There was a woman in the same field as me who had killer fashion sense, I always judged her skills above mine. And then I saw her work. It was amateurish! At best. I had wrongly assumed her ability to dress herself coincided with any of her other abilities.

I told that story to date guy, and since he had just started a new job I dragged him to a department store to update his wardrobe and insisted he dress for the career he wanted. I ran into him 6 months after the relationship ended and he was still dressing in a clean, professional matter.

If someone told me I needed to wear heels and get eyelash extensions, I'd dump them pretty quick. If it was more a matter of looking my best, with well fitting clothes, I might be more interested in talking shop. Start a conversation with him about clothing style and figure out where he stands on the issue. Some people like being dressed up, others take it as a personal insult. Men don't tend to have the same emotional minefield when it comes to perceiving their significant other attempting to objectify them, some will appreciate a bit of advice. If he doesn't, well, now you know.
posted by Dynex at 6:53 PM on July 10, 2012 [1 favorite]

As a hopeless dressing guy, I would actually appreciate the help. Ask him if you can go shopping with him?
posted by xammerboy at 7:06 PM on July 10, 2012

Please talk to him about it. My brother was so similar, and thank god for my sister in law who talked to him about his 'fashion'. Turns out, my brother was just sort of winging it without caring at all. She did some selecting culling in his closet, and things are so much better now. I think having a sense of humor was hugely important.
posted by Nickel Pickle at 7:22 PM on July 10, 2012

As a "hopeless dressing guy" by many external standards, I would loathe being told what to wear, or how to wear it, and I freak out and the very idea of replacing my ratty, well-loved clothes with new stuff. Shopping for clothes and shoes Is Not Fun.

Many women (not all, a few share this view) struggle with the concept that forays to buy new clothes are less enjoyable than my yearly trip to the dentist.

I generally agree with headnsouth and disagree with anyone who tells you to change things too much. If you feel the need to, do so in small, subtle ways over time. It's possible he might want to change.

However, I agree with the whole work function advice. Let him know what's expected, and if he wants to go run through his outfit. It's okay when you do this because he's on your turf.
posted by Mezentian at 7:23 PM on July 10, 2012 [1 favorite]

tell him that there's a de facto dress code in place in your professional milieu and it would make you happy if he wouldn't mind adhering to it. -facetious, edited by me.

This. Tell him this straight up. Ignore all the passive-aggressive hinty stuff, don't try the extremely-slow-and-likely-entirely-ignored, "you look so nice in that shirt!" approach, don't take him shopping (not yet, anyway).

Because that's really the first part of your problem with how he dresses - "I don't want to invite him to work functions/receptions for fear of what he'll wear." It's a relatively small, concrete, solvable problem with a specific reason behind it. You're not trying to remake him, you're not trying to mold him, you're not trying to fix him, you're just trying to get him engage in a little social camouflage. Hell, phrase it as, "These people are a bunch of squares, but we'd both feel a lot more comfortable if you looked a little squarer when we're out with them."

How he reacts to that conversation will tell you a lot. It's entirely possible he's just clueless - if he says, "Huh?? What's wrong with what I wear? Help!", then hey presto! off to the store you go.

If he says, "No Effin' Way! I look great and I won't let The Man force me into his Clothing Prison!" . . . . well, now you know that he dresses like that on purpose, and you can make of that what you will.
posted by soundguy99 at 7:29 PM on July 10, 2012 [8 favorites]

I think that the responses suggesting that you take a meandering, indirect, secretive approach (go shopping and try to influence his purchases, show him pictures of men's clothing that you like) are in some cases too subtle, and generally just a little bit manipulative-yucky.

If you don't like how he dresses, just like anything else, you should first decide if you can let it go or not. If you can let it go-that's best; this probably isn't a huge deal. But if you can't handle it (if you could just ignore it, you wouldn't be posting this question), be gently straightforward(I prefer it when you dress like___). It's possible to be straightforward without being mean. He may decide that he is or is not willing to adjust. If he is, cool. If he is not, again, decide whether this is something that you can let go.

In day to day life, if you can let it go, accept his fashion choices. Don't go trying to change his daily wardrobe unless he asks you for help. This is your problem, not his. Don't let it niggle at the back of your mind.

At special or social events, on the other hand, where you think what he wears is important or a reflection on you, ask him if he'll dress a specific way. That's a totally reasonable request, and you'd surely do the same for him if he asked you to now and again.

And if you can't let it go, and he can't change, maybe you shouldn't stay with him. It's a small thing that seems shallow, but anything that's constantly at the back of your mind, bugging you, making you want to nag at him or be embarrassed by him or wanting to change him, is not good for a relationship.
posted by windykites at 7:35 PM on July 10, 2012 [1 favorite]

Does he have ANYTHING you like? My ex had a couple of good sweaters and one pair of good jeans, and i COMPLIMENTED THE FUCK out of those sweaters and jeans. And basically he ended up wearing those more often, and when he bought new stuff it would be more like the stuff i liked. It's a process though.

Can you make 'let's go shopping' an activity? Go to a place that sells both mens and womens clothing (a department store? Gap/banana republic?), so you can make like this is 'for both of you'. Get him into a change room and just start bringing him shit you like. And tell him he looks sexy in it! And he'll probably like it too.
posted by Kololo at 8:06 PM on July 10, 2012

Hmmm, I don't see how you can provide fashion guidance so early in a relationship.

Ha! After we'd been dating for a month my wife told me she'd been plotting to cut off one of my t-shirts in a moment of faked passion just so she didn't have to look at the thing anymore. You can do this - it depends on how you do it and what he's like.
posted by Dasein at 8:16 PM on July 10, 2012

I think it's fair to dress to please each other from time to time. Much like lingerie in private, if you phrase it as "I'd like to dress you in what I think makes you hottest - and secretly I'm also hoping you'll like it too so you'll dress for me more often" then I don't think it's an affront.

The catch is that if he doesn't like it, you may have to accept that (or try a different style), and your outfit might be outside his comfort zone, which may mean you have to buy the outfit (he may be reluctant to buy what he's unsure of, and this may emerge in humming and harring that results in an ultimately unsuccessful shopping trip). You might also want to be careful where he first wears it - some people when pushing their comfort zone might want to avoid the outing being a night surrounded by friends, while others might be exactly the opposite.
posted by -harlequin- at 8:26 PM on July 10, 2012

I suggest approaching it as something that you are excited about, and would make you happy. A positive thing, rather than an criticism of what he is currently wearing.

"I've been thinking... Is it alright if dress you?" (...implying almost a fetishy thing, but making it clear that you aren't thinking of diapers or feathers or boot-cut jeans or other creepy stuff.) ...Buy you some clothes that I like?"

Basically, you are saying that dressing him up is something you would enjoy, and is low risk for him. If he doesn't like the results, then fine, no problem. If you are both happy with the results, (likely, as you'll be complementing him on how nice he looks) then he will be more receptive to your fashion advice in the future.
posted by Anoplura at 9:18 PM on July 10, 2012

Style is a personal thing, so it may not make sense for the OP to impose hers on the guy. However, proper fit is universal, and paramount to not looking like a slob.

Primer Magazine has a handy guide about shirts, pants, and jackets should fit.
posted by ikaruga at 9:18 PM on July 10, 2012

I fear the hats might be a tell. If they're baseball hats then yeah, that may be just a college holdover. But in my experience, most men who wear hats i) care about expressing their identity visually, and ii) think they're good at it. Nobody wears a fedora, a derby or even a hipster knit cap, just because. They all think they look awesome.

The many oddly-dressed guys I have dated were all like that --- deeply invested in their personal style. Some were just odd in a kind of timeless way, but others seemed to have frozen their sense of style (whatever it was) in their twenties. Those guys in my experience were absolutely unbudgeable, because they were in effect expressing nostalgia for a particular time and place through their clothes. It was all emotional: not explicit, not rational.

So soundguy99 is right: open the door by asking them to adhere to a particular dress code for a one-off event, and see what happens. You'll get your answer right away.

(And I agree with windykites that it would be icky to be indirect and manipulative about this. I had a friend who behaved like that -- she used to do things like "accidentally" spilling paint on her partner's out-of-fashion pants, or somehow "losing" his beloved old jean jacket in the laundry. It was kind of a vicious circle -- she didn't really seem to fully respect him, and then she did things that expressed that lack of respect, which fed the cycle.)
posted by Susan PG at 10:24 PM on July 10, 2012 [5 favorites]

Another vote for the direct approach and for speaking of dressing for the occasion. Describe the clothes the code calls for. He might not have ever had any reason to think about this.

If he has always been in a profession where what he wears is of absolutely no concern, and if he was brought up without much guidance on the subject, he might never have had much opportunity to learn how to dress appropriately, and just sticks with comfortable clothes and some vague idea of sometimes wearing a coat and tie. Also, some men don't realize that it is necessary to spend a bit of money on a variety of garments for different occasions and therefore don't have much of a wardrobe to choose from.

Such men can be diamonds in the rough but their wardrobes can definitely need a little polishing. Years ago my sister-in-law was heard to compliment a woman on "how beautifully she dresses her husband." She herself married a great diamond of a man who had never had much guidance about clothing and was colorblind besides. She dressed him quite well--which he appreciated a great deal. It helped him in many ways.
posted by Anitanola at 11:46 PM on July 10, 2012

A couple of things. These are based on my experiences and are not meant to be extrapolated to all men.

One, while you would presumable take criticism, even constructive criticism, of your appearance or wardrobe very personally, do not assume he would. Two, I suspect this will all hinge on how he feels about spending money. If he's a tightwad (which is a fine thing to be), it is going to be a non-starter unless you are a pair of master thrifters. Three, no offense but The Art of Manliness is not accessible to people who do not have a functioning fashion vocabulary. ("So, what's your style?" "Uh. Dressed?") Four, shopping is not fun for people of any gender who do not enjoy it. It just is not. So if you get any traction on this at all, you need to make that outing as fast, painless, focused and rewarding as possible.

I would basically just up and say "Honey, I think you need to update your wardrobe. What would you think about a trip to One Store next weekend?" Pick a time when you are both naked or in PJs or whatever so it doesn't become about what he's wearing right at that moment.
posted by DarlingBri at 2:33 AM on July 11, 2012 [1 favorite]

From your description, it sounds as though the way he dresses to go out is purposefully different from others and highly personally expressive. I would suggest that his aesthetic is very much part of how he sees himself. He is not "clueless"; this is him, and any rip on his chosen style is a rip on him.

I would frame the conversation about work-function clothing as a cunning disguise, a form of normal-person incognito. A conspiracy that includes you both, rather than a flat-out "Your usual dress is inappropriate for this, here's what you have to wear."

For his day-to-day look, maybe reflect that you are dating an interesting person, and his aesthetic is a reflection of that.
posted by Pallas Athena at 3:28 AM on July 11, 2012

I have been in this exact situation, including deciding whether the terrible clothes were, in fact, a deal-breaker for me. It's very tricky. I decided to stay, and over the course of 5 years the man in question did "fix" his apparel by leaps and bounds and is now more concerned with his appearance than I ever was (what monster have I created?).

Like you, I felt it was too early in the relationship to straight up dictate clothing or to go out of my way to purchase clothing. But it was far enough into the relationship that I needed to introduce him to my friends and....that was a troubling prospect.

I took what I think may have been the high road and simply tried to figure out what.the.fuck was going on with his clothes. After it was obvious this man had no good outfits, I would regularly point out men's clothing that I liked and asked him what he thought of it (but without any subtle subtext or anything - just honest questions). Often, he would have no opinion. But sometimes he would offer extremely concrete and specific reactions to certain "looks". This was helpful for me to figure out where he was coming from in his own wardrobe. I could initiate a conversation about clothes without it being explicitly about him. Gradually he started to become more interested in men's clothing and one day just clued in (though, I should caution you this day was more than a year in to the relationship!).

If, as someone up thread suggested, his fedora and medieval footwear are a giveaway that he does think he has a "style," then this would be a good opportunity for you to understand where he's coming from. Something like, "Hey, I notice you really like shiny shirts/doublets/snakeskin loafers....what do you think of this?" and then point to an article/outfit that is a more stylish version of what he is attempting to achieve. Just find out how strongly he feels about these items and see if he is amenable to some direction. If he likes it, say "I bet you'd look really good in that!" If he doesn't like it, ask why. The more he has to articulate his own preferences, the more likely he is to be open to a conversation about them.

The one thing I would say about telling him what to wear for work functions is that while I don't think that is inappropriate at this point in the relationship, it doesn't help OP much if the man simply does not have dockers and a polo. If you tell him "it's business casual - button-down and slacks" then he will wear his shiny button-down and his voluminous pants. So .... perhaps just slow down on the workplace invites for now?
posted by Mrs. Rattery at 4:11 AM on July 11, 2012 [1 favorite]

Some of my best friends are a couple who has been together for 20+ years, married for 12.

She: works an extremely high-powered tech job at a company that rhymes with "Nicroloft". She wears very smart, pressed, preppy suits to work. On the weekends she lives in khakis and Gap.

He: works a moderate job as an IT guy. Wears khakis and a shirt that is ten sizes too big to work. On the weekends he lives in cammo cargo shorts and mid-calf doc martin boots. He wears Prada glasses and has piercings.

They are the coolest, cutest couple ever.

Let it go. Pick and choose your battles and don't try to change anyone.
posted by floweredfish at 6:54 AM on July 11, 2012 [1 favorite]

If you're close enough for him to be coming to work events with you, you're close enough to ask him to change what he's wearing.
Don't make a big deal out of it or approach it with heightened sensitivity unless you think that he is going to have a complete breakdown. It's a shirt; it's not his sense of self. If you come at it like that, there is a large chance he will too.

Changing someone's clothes is one of the easiest things to do.
Changing someone's style is not.
Figure out what his style is and what style he likes, and then see if there are items that fit into that category that you would be ok with.

I did this. My bf likes preppy clothes but he was wearing khakis and too-wide shirts and other things I didn't like. Now he wears things that are still his style and are the fit and looks that I like too.
Compliment him when he wears something you like. When you have a date or work event, ask him to wear a particular outfit he owns that you like "Would you wear that white shirt and the gray pants? You look so cute in those."
"Honey, I don't think this is a hat occasion. Can you leave it at home?"

As long as he doesn't define himself by those particular pieces of clothes you dislike, it shouldn't be hard to find common ground that you will both be happy with.
posted by rmless at 9:38 AM on July 11, 2012

I dunno how serious you are about this, whether you're looking to overhaul his entire wardrobe or if you just want him to spiff up for certain events / social gatherings. Let me just say this, cut the crap and be upfront about it. Us guys know we (generally) have lower standards of dress than our female counterparts (ie: we usually don't give a fuck, or very little of one.) If he's an IT guy and works from home, I can guarantee he is at the farthest extreme of not giving a fuck.

You're early in your relationship, if this is seriously an issue, just calmly hash it out and see if you can come to a compromise. If you try to be coy and suggestive it will come off as naggy, annoying, critical, etc. Be upfront, tell him you two have different styles, and you want to compromise or offer suggestions in his dress sometimes. You probably can't change his complete style, but I bet you could convince him to dress up to certain events and gatherings. I think it'd be better to lay it out on the table what you're feeling, and either he shrugs and accepts it (very likely), or he balks at the massive change you're introducing to his life and leaves, in which case you didn't waste too much time with him.

This is coming from the perspective of a nerdy IT guy who's dating a fashion retail student, so I have a bit of experience ;)
posted by el_yucateco at 10:12 AM on July 11, 2012

Personally, I'd say something like, "I would love to bring you to work event X but it would mean you'd have to wear something more like Y. Would you be up for that? I'll buy the stuff. I hesitate to even ask, but that's how our company dresses."

Everyone I've dated has understood that different roles have different uniforms. You don't wear the same clothes to your gf's work event that you do to your buddy's LAN party, and changing clothes doesn't mean selling out if it's a favor to your gf's career.
posted by small_ruminant at 1:43 PM on July 11, 2012

If he's adamant about the hat (and, uh, my user name says hi), then try to move into getting him to wear nice hats properly instead of like a douchey person. The basics of this include:

1. Get a nice hat. It shouldn't be one of those tiny-brimmed, cheap-plastic-covered-in-fabric jobbies that you see a lot for like fifteen bucks. Get him a proper old man hat.

2. Get a jacket or coat that either matches it or complements it. Hats like that are winter wear to begin with. I tend to wear a black pea coat with a black, wide-brimmed hat and it looks legitimately good, because they are items that go together in a logical manner.

3. Same goes for summer wear. If he does consider himself a Hat Guy, try to find, say, a light fiber panama hat or something that would be light enough for summer. The idea is to find the proper tool for the job.

Long story short, the reason that People Who Wear Hats have such a well-deserved douchey reputation (that I myself subscribe to) is because they tend to just find the cheapest, crappiest thing that'll fit on their head and then wear it all the time, especially when it's inappropriate to be wearing a cheap, crappy hat, such as all the time. In other words, the same advice that everyone here is giving about every other article of clothing: get a good one instead of a cheap one, and aim to wear it properly.
posted by DoctorFedora at 10:31 PM on July 11, 2012 [1 favorite]

I used to see a guy who was incredibly intelligent, and either didn't care for appearance or thought thinking about it too much was the act of a shallow person. Some of it was stuff that just wasn't my taste - keeping longish hair but not looking after it, tucking in his shirts all the time (I don;t know if this is the case in the US but it's seen as very naff here to tuck your T-shirt/shirt into your jeans) dressing like a 90s Whose Line is it Anyway contestant with the slacks and the coloured shirt - you know how some American guys just wear a shirt and those brown pants, or software logo T-shirts all the time? Some of it verged on embarrassing, such as wearing a snot-coloured anorak with a rip from armhole to hem that he tore and couldn't be bothered to get fixed, or wearing jeans with washing tablet residue all over it. I'm not a fashionista, but I see clothing as a form of expression, and it confused me that someone could genuinely not notice or appear to care about what he put on each day.It would be glib to suggest that it was one way that I realised that we were never destined to be more than a fling, but it was definitely a difference. Not a clash of styles, but more an absence. He stayed in academia where such things matter less, but I would have found it difficult if we were both in professional environs.

What I've learned since is that a large number of men do not like shopping. They don't feel comfortable in a clothes store as they might in a supermarket or a computer shop or other places where one can acquire goods with money. Men's clothes stores always seem drab and dark coloured to me, and I think that's because a lot of men are afraid of standing out for one reason or another. (When I think about my parents, I'd be surprised if my dad ever actually chose a piece of clothing after getting married. The suit he wore to my graduation was late 60s/early 70s, and not in a good way.) Also, a lot of men seem to buy clothing too big for them for some reason - I had an ex who dressed like grunge never died well into the 00s. Sometimes I've bought partners clothing because I knew they hated the experience of having to go into a clothes store and pick something out - but if his clothes are really objectionable, this can be a subtle way of improving things a little. If it's a professional issue, and you think he's really embarrassing himself, can you suggest he goes to see a personal shopper in a department store, or the two of you could go together? My SO and I participate in geeky hobbies where there are people who like to dress a particular way - like others have said, it's the identity of the geek or the coder or what have you - and if your guy is the same it might work to try and adapt this.

Also, DoctorFedora is right. I like hats. I am well aware that wearing a beret marks me out to some as twee or pretentious, but I like them, so fuck that. Men should wear more hats in my view, and it's a shame that Hat Guys are besmirched by incorrect hat behaviour.

From a guy's point of view: each woman has a different sense of style for "her man". You can go from dating the woman who likes skinny jeans and corduroy coats to one that likes a $200 pair of Luckys and polo shirts.

I genuinely don't know what you mean by this. Women change their wardrobe according to whom they are dating? Not the case here.
posted by mippy at 9:54 AM on July 12, 2012

From a guy's point of view: each woman has a different sense of style for "her man". You can go from dating the woman who likes skinny jeans and corduroy coats to one that likes a $200 pair of Luckys and polo shirts.

I genuinely don't know what you mean by this. Women change their wardrobe according to whom they are dating? Not the case here.

Erm, I'm pretty sure zombieApoc means exactly the opposite from how you read it - women change the man's style, not their own style.

i.e., I date "Woman A" who really likes how i look in dark jeans & light polos, and then a year later "Woman B" is going through my closet saying, "What the hell is up with all these pastel polo shirts? These are horrible. You need some dark button-downs."
posted by soundguy99 at 10:31 AM on July 12, 2012

I used to be a bad dresser. I wore THE most boring clothes ever, and they were always a little baggy because I felt weird about being skinny and because I had no fashion sense at all. Simply put: I didn't know what looked good and what didn't.

The trick for you is to figure out if he will let you help him, style wise.

It was a HUGE help for me when I started dating a really sweet woman who told me what she thought rather than telling me what I wanted to hear. I wanted to hear that I looked good, because we all think we have some sense of style, right? It's just like how everybody thinks they have a great sense of humor even though they couldn't spot something funny if it slipped on a banana peel and landed on a whoopie cushion right in front of them! [tangent: How is "whoopie" not in my spellchecker? Hhmmph!]

My ex took me shopping and said "Let's try something different." At first, it was like a game. We spent a day pubbing and shopping, trying out completely different looks. The beer breaks felt like a reward for my patience, buuuuuuuuut, what really made a difference was seeing myself in different styles of clothes than I was used to. I realized I could EASILY be a much better looking guy. And now I am. WHEEEEEE!

If you take my tidbit there and try it, here's a piece of advice: TAKE PICS. Whenever I go shopping for new glasses, I ALWAYS take pics of myself in pairs of glasses I'm considering. It's way too easy to veto anything that looks different than what I'm used to when I'm standing in front of a mirror in a store... but when I get home and see the pictures, it's so much easier to recognize what looks better on me and what doesn't.

This works, IMHO. YMMV. Offer not valid in all states with all boyfriends, some restrictions apply, etc. Good luck!
posted by 2oh1 at 4:02 PM on July 12, 2012

I know there's a lot of relationship advise in Metafilter that says, "You can't change people. You shouldn't try to."

I think that this is true, but also a little glib. You can't change something that is fundamental to a person and which they care about. But not everyone cares about everything.

Exactly this.

You need to be talking more about clothing, in a general way. You seem to have no idea if he wears these clothes because he likes them, likes them a lot, or simply ignores what clothing looks like altogether and is simply wearing these things because they are in his closet and haven't yet gotten so tattered that he would be risking indecent exposure. Some men really don't think about these things -- I have actually had to insist that a male friend of mine put on a different pair of pants when the holes in his were literally past that point yes, THAT point, and there is no way talking to a guy you are dating can get anywhere near that kind of awkward.

You don't have to bring this up like it's some embarrassing Thing That Shall Not Be Named. You're getting to know each other, presumably... find out what his habits are around clothing, around shopping, if he likes to change up his style every few years or stick with the same things. Talk about what yours are too. Ask him what that style of shoe is called, or if he has winter and summer hats.

On hats -- the very best place for a man to upgrade his hat would be at a man's hat shop. The shape of the hat is very important, if it does not complement a man's face and body it looks out of place. A good hat shop should have someone who can help in choosing a style of hat that will look great. OTOH, if he wears novelty hats shaped like hot air balloons or something you might have to take the direct route and ask him to please not wear that hat when he is out with you.

If you want him to wear business casual to a work function of yours, you should find out what he has to wear that he feels would be appropriate for business casual. If he has nothing that you feel would be right, ask if he would wear a particular thing as a special favor to you to help you fit in with your work culture. Buy it, and make sure it is comfortable for him to wear.
posted by yohko at 6:16 PM on July 12, 2012

About the "guys wearing baggy clothing" thing: I know several tall people, male and female, self included, who have a choice: either buy clothing that's too short in the arms/ hems/ cuffs but is fitted nicely, or else buy things that are long enough, but billowy. Being tall is really annoying when shopping.

Another thing is that someone who grew up getting their clothes secondhand from either their siblings or a thrift store may not know how things are supposed to fit. I don't know if that's applicable for your guy or not.
posted by windykites at 8:33 PM on July 12, 2012

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