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Boyfriend Is a Bad Dresser

Group Therapy: My Boyfriend's Style Embarrasses Me

This question is from a Group Therapy post in our TrèsSugar Community. Add your advice in the comments!

Okay, so basically my new guy is super good looking and totally sweet. We've been dating for about a month and I really like him — it's perfect for me right now and has the potential to become something big, although we're taking it slow and getting to know each other right now.

Anyway the only problem is that he has a sense of style that I just cannot STAND. I hate to be shallow, but he wears loose ribbed turtlenecks with baggy jeans and dirty sneakers and then throws an old, not well cut, kinda too long, leather jacket over the top of all that as the finishing touch.


Don't get me wrong I'm not the most fashionable woman in the world, but my guy's wardrobe . . . hate to say it, but it's true: embarrasses me. My best friend keeps telling me to go shopping with him, but we're not big shoppers in general and I think he would think it was a bizarre proposition.

And anyway I sort of don't want to be subtle about this, I want to straight out say: "hey, you're wardrobe is just atrocious," (and since he doesn't much care about fashion) maybe he'd be open to a new look?I really don't want him to get defensive though — help!

Have a dilemma of your own? Post it, anonymously, to Group Therapy for advice, and check out what else is happening in the TrèsSugar Community.

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marieli marieli 6 years
Well since it's almost christmas, this should be pretty easy for you. Tell him you want to go shopping for gifts for your family, take him along, and casually suggest you go in a clothing store. Have him try some stuff on, you could try stuff on too so he doesn't feel uncomfortable. Make a date out of it. just have fun with it !
JoeTyndall JoeTyndall 6 years
Searching Soul, This brings up two important points. The ‘limbo’ relationship The OP is dating this guy, and it is clear that she is dating him exclusively. But it is also clear that they are not officially boyfriend and girlfriend. Unfortunately, this has placed the OP in the worst of both worlds. She is not free to date other guys, but she is also not able to communicate with her ‘date’ and get emotional support from him the same as if they were boyfriend and girlfriend. The OP needs to make it very clear that she is either free to date other guys at the same time, or make it official that the two of them are boyfriend and girlfriend (and get out of this middle ‘limbo’ that she is in). In my opinion, this also refers to people who are ‘friends with benefits’ — they need to either make it clear they are free to sleep with other people (they are ‘just friends,’ right?) or make it official that they are boyfriend and girlfriend. Of course, most people do not, and they end up in the same bad ‘dating-limbo’ that the OP is presently in. discussing each other’s character flaws and personality weaknesses The big question is, when should two people start discussing each other’s character flaws and personality weaknesses? They should start discussing them as soon as they become boyfriend and girlfriend or as soon as they start sleeping together. The OP has placed herself in a ‘dating-limbo.’ (1) She needs to either tell him she is free to date around or (2) officially become boyfriend and girlfriend, in which case they need to immediately start discussing their each other’s character flaws and personality weaknesses. If they do not want to discuss each other’s character flaws and personality weaknesses, they have no business calling each other boyfriend and girlfriend, and they need to get out of the relationship.
katialoves katialoves 6 years
no no no! don't do anything. it is way too soon. it could really bother him that you are so annoyed by a little thing like fashion. it could also/alternatively bother him that you are bold enough to tell him to his face so soon in the relationship. and/or that you dont love his clothes. and/or that you think he should take your advice. start by buying him a jacket that you like for an xmas present. just sth which is not hideous. and sth that you think you could have some leverage in convincing him to wear once in a while (more and more).. as in a 'reason' to wear it instead of his fave leather thing, ie its more formal or something. after christmas when there are sales go shopping for yourself and stumble on a new pair of athletic shoes and maybe some long sleeved tops. dont tell him you dont like his stuff/style unless he asks. if he asks upon receiving gifts of apparel, be careful how you say things. as i think miss sushi was saying, relationships are not about changing people, but if he's great in other ways, thats already amazing; if your taste wears off on him, thats bonus hope you guys have a happy holiday season together...
searching-soul searching-soul 6 years
@ Joe Good advice,you can't just say to someone-the way you dress sucks. Not only will he most likely be offended but it opens up a Pandora's Box in terms of your own flaws. This guy may turn around and say to the OP because she's being so brutally honest there are things he does not find so hot about her either .Then both parties are saying hurtful things and the relationship will only go downhill from that point. A month is too short of a time and he will wonder why she is already trying to change him and is not accepting him for who he is. @OP You liked him enough to date him so stop trying to change him. He will see it as controlling and will rebel and you will cause unnecessary tension. New relationships are fragile, don't take for granted that he will stay with you if you criticize his style/looks so early. People can be funny when it comes to their feelings and their egos. Give the relationship time to go somewhere and later on approach the subject lovingly and with sensitivity.
JoeTyndall JoeTyndall 6 years
Oops, typo, should be ...(I am a guy)...
JoeTyndall JoeTyndall 6 years
Searching Soul, I agree. Some people are just not open to such suggestions. I have a lady friend I am a guy) and she always wears dumpy clothes. (She always wears baggy T-shirts and baggy pants.) She is not fat, in fact she has quite an attractive figure. But her severe lack of self-confidence subconsciously makes her want to dress in a dumpy way. (Dressing sharply and snazzily would bring her a lot of attention from guys, and she would not be able to handle it.) I thought about telling her she looks dumpy, but I didn't, because it would cause too much trouble. When we have friends who dresses too dumpy, we first must be willing to bring up the subject of them not having enough self-confidence (and bringing it in a tender, not hostile way) before we tell them to stop dressing in a dumpy way.
searching-soul searching-soul 6 years
Maybe later down the line you can tell him I think such and such will look hot on you once you know him better. A month is way too soon. Take it from me, I did that to an ex early in my relationship and he never got over it and would throw it in my face when we argued. You can say how handsome you think he is and such and such would look great with his complexion, body type etc. but don't push it.
Pistil Pistil 6 years
Go ahead and buy him some new clothes. I know a lot of girls who kind of dress their guys that way. But I wouldn't tell him you think he looks terrible. Even someone who doesn't care much about being stylish doesn't want to hear that. I wonder what attracted you to him in the first place if his wardrobe is so atrocious and embarrassing? Sometimes my boyfriend wears dorky t-shirts out. But I realize that I'm more worried about what everyone else thinks, and what does that matter? I'm not dating someone to impress anyone. I am in fact a dork dating a dork.
Studio16 Studio16 6 years
Just buy him some new clothes that you like and be all, "Oh, honey, I saw this while I was out, and thought it would look great on you. Try it on!"
MissSushi MissSushi 6 years
uh, you can't blanket statement men in such a way, GTCB, just the way you cant blanket statement anything. Everyone is different. I don't like my husbands wardrobe in the least. In fact, I despise it. He is way too preppy, tucks shirts in, wears incredibly outdated patterns, and a ton of other things I don't agree with. But you know what? It doesn't matter how I feel about it. It's what he likes, what he feels comfortable in, and is a part of him. He knows how I feel, and I know how he feels, I don't lie if he asks me if I like something. I just don't think you get to flat out tell someone to change their way of dressing. What if my husband told me to lose my jeans, skater shoes, and hoodies? If we went shopping together, and he insisted I buy slacks and a braided belt? It wouldn't go over well. Bottom line - you can buy him gifts in styles you like, compliment him when he wears things more to youre liking, but you can't insist that someone change their wardrobe to suit your liking. And honestly, you're wanting to do this after a month?
bethinabox bethinabox 6 years
Haha I have this same problem with my boyfriend... I rarely see him in anything other than his work clothes (black pants and a white short sleeve button up), or tan pants with one of two blue sweaters/sweatshirts and a white undershirt. But I know he is very tight on money so I don't wanna make him buy new stuff, and I don't know what to buy him, size OR style wise, so I dunno! Plus the undershirts and his work shirt are all very dingy... I might start by buying him just new plain shirts and go from there... LOL. Good luck to both of us...
Gdeeaz Gdeeaz 6 years
Offer to go shopping with him but if he says no then leave it alone. If it is his style and he likes it then don't try to change him. I would be very offended if my boyfriend told me I had bad taste (as would most women), and now a days guys are the same way.
JoeTyndall JoeTyndall 6 years
I want to add I would be very offended if a girlfriend told me, "Dude, I'm sorry, but you need some new clothes."
JoeTyndall JoeTyndall 6 years
OP, It really comes down to one question: Is he interested in getting some feedback and learning how to dress better, or will he be offended by it? Ask him! If he is offended by this (and a lot of us guys are), then don't push it. I'm assuming the trust, friendship, honesty, and teamwork between the two of you is good enough for you to be able to ask this question without him getting angry. Is it?
postmodernsleaze postmodernsleaze 6 years
I agree with GTCB. The next time you're with him, say, "You know what you'd look great in? [insert clothing here]." I also agree about lending advice one clothing piece at a time, as it will seem less like a full-blown crazy lady attack. Start with the leather jacket. There's a lot of leather jackets out there that are really nice (more James Dean sexy than old and baggy). Inch your way through his wardrobe. Aaaand, if that doesn't work, just be blunt and say, "Dude, I'm sorry, but you need some new clothes."
elramos elramos 6 years
I think your best friend is on the right track about shopping. My boyfriend when we began dating also had bad clothing style. I never came out and told him I hated everything. Although I did had to break down and tell him I hated a certain pair of jeans he had, because I seriously couldn't stand them. He took that criticism fine, but it was because I was complaining about a certain pair of pants, not his whole wardrobe. I helped him by taking him shopping with me, and pointing out things in magazines and TV that he would look good in. Me introducing him to different stores and showing him things I thought he would look good in, helped give him confidence to try new things. Maybe your guy doesn't know anything else, and is scared of venturing into new clothing territory. Go soft on him and gently push him in the right direction, don't rip his head off.
atraditionalist atraditionalist 6 years
Just tell him you think its so hot when guys wear X item - men always want to turn a woman on lol. When he wears x item tell him how sexy he looks etc..
Natalie-Love Natalie-Love 6 years
If I were you, I would pick take it one step at a time. Telling him his whole wardrobe is terrible might come of as you trying to change him completely.I would say- pick your battles. Choose your least favourite item (eg. the poor fitting leather jacket) and encourage him to buy a new one, because you don't like that one's fit on him, don't suggest he change everyyyything, but as example, he can still wear what he likes (leather jackets) but help him find a new one that's rockin' (cause guys can look reallly sexy in a nice motorcycle bike). After he has a nice jacket perhaps buy him a few nice polos for christmas, etc. Changing a guy completely probably shouldn't be your goal, but I'm sure a few small steps can make a big difference.
Janine22 Janine22 6 years
LOL! My fiancee was a terrible dresser when I first met him too! I'm talking polyester shirts and pleated old man pants! Luckily I worked at the Gap at the time and I just slowly bought him clothes when there was nice things on sale and he wore them. Now he looks good. He admits that he had no clue before. I don't think that he was offended at all, he appreciated the help. I agree with the other girls, you do not want to make really mean negative comments, but it is ok to tell him that he could look so much better than he does. I agree with GTCB, guys are not as sensitve about this issue as you might think. Good luck! :)
GTCB GTCB 6 years
You might be surprised to learn that men don't always take offense at fashion advice from the fairer sex, especially girlfriends. If you couch it in the right terms, something about him maximizing his looks/appearance, this should go over just fine.
Rjs-baby-girl Rjs-baby-girl 6 years
Looks are a sensitive matter and I would not recommend the way you want to tell him, He will feel like you are attacking him and might feel pretty insulted. I know I would if someone I was dating for a month told me my clothes are ugly. You started dating him with him wearing these clothes and you cannot plain ask him to change his looks now, you can't change him. But, like Alex1988 said, you can take him shopping and make him try on clothes and use positive comments to make him feel good about it. The key is that a positive approach will always win over throwing negative comments to his face. I would start by looking at ads with him and showing him clothes that I think would look good on him, and see his reaction. Then another time I would ask him to go shopping with me because I want his opinion, and use the occasion to make him try clothes too. If you really care about him and his feelings use the soft method.
Alex1988 Alex1988 6 years
Well since it's holiday time, this should be pretty easy for you to deal with. Tell him you want to go shopping for gifts for your family, take him along, and casually suggest you go in a clothing store. Have him try some stuff on, you could try stuff on too so he doesn't feel uncomfortable. Make a date out of it. Remember the things that looked good on him, or what he liked, and buy him a couple items for Christmas. Mention to him how great he looks when he wears his new clothes, and he will get more. It will probably take a while to get him wearing normal clothes all the time, but it's a start.
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