How Do You Politely "Guide" Someone's Fashion Choices :)

You don't, you let people be who they are. If you feel you need to change him in order to be with him then he is not the one for you.

I have been buying my husbands clothes and dressing him for years and years. I tell him what to wear and what not to wear. He doesn't care what he wears and I do, so this works for both of us. Why not ask him to go clothes shopping together as a date?

Post-divorce, I dated several military and ex-military guys. Most of them looked smokin' HOT in uniform and not so sexy out of it because they did not know which civilian clothing looked good on them. Direct approach was best.

I am a 47 year old scientific sales person. My boyfriend is ummmmm unconventionally younger than me (veterinarian, speaks seven languages, smart as hell) but much younger. I met him when he was in scrubs but he is a complete rocker dude and I can't imagine trying to get him to deviate from that.

I have to laugh because last month when we were in the Lexus Dealer for him to buy a new car. He was off work that day and dressed as his usual younger, hot, rocker dude self and I was all business, looking like I came straight from court prosecuting someone who looked like him. They couldn't figure out what our deal was, we think it's pretty funny.

He's smart enough to show up a great suit when necessary but he is who he is and I love dressing down in a concert sweatshirt,jeans and black Converse.

You don't tell another adult what to wear unless asked for your input. He's a grown man, he knows what he likes to wear.
My ex loved loud Hawaiian shirts. I find them hideous. And the last Christmas we were together, I bought him THREE of them. Why? Because HE liked them.

ETA: You said that he says he "values your advice," not that he asked you to dress him. If a guy asks me, "Do you like the red tie or the black tie better?" I'm going to choose either red or black, even if I think they both clash with his shirt, and the best option would be the purple one. Why? Because HE has already narrowed it down to the two that HE likes best. If he asks, "What color tie do you think goes best with this shirt?" THEN I will tell him that I think purple is the best choice. Saying that he values your advice does not mean that he wants his own episode of What Not to Wear.

are you officially divorced? How are your kids handling you seeing another man? I bet that's a huge change for them.

If he has asked - he knows he needs help, so, tell him to pull out his check book and you're going shopping with him. He needs a new, updated wardrobe.

you're scared to say something because it sounds really vain and shallow and you don't want to associate yourself with vain and shallow, right?

If he looks good in Hollister - who cares? Hollister has long sleeve shirts, not just T-shirts.

So you either need to fess up to being vain and shallow (not meaning to be rude or mean - just stating the obvious here) and tell him what you expect in a "man's" attire/wardrobe. Or just stop worrying about it and see him for HIM and not just his clothes.

"Does your son know you are stealing his clothes?" =)

Instead of focusing on telling him what not to wear, why don't you offer to go shopping with him? Maybe on the lines of "hey - you have any interest in updating your wardrobe? I saw this nice outfit the other day and it would look so amazing on you." If he is offended then perhaps its better to know that about him now before you guys become too serious. Especially if it is that important to you. Good luck.

I hoe you let us know what happens =)

Okay, you're overthinking this.

He's already ASKED you for fashion help. Men don't ask for help unless they're prepared to accept it. So that part is done. You don't have to worry about offending him.

Ask him when he wants to go shopping for clothes, because you're so excited about helping and giving him fashion advice. Go to a nice department store and pick out an outfit that you know will look great on him, and encourage him to browse and bring you things to get your opinion. When he brings you things you know will look dated or too small or whatever, gently disapprove the choice. "No, I think you're too young and fit to be wearing that style. This other cut would flatter your physique much more." Or, "I think that if you really want to wear the Hollister style Tees, you need to wear one in your size. Your shoulders are too big to wear your son's. But I think that you look sooooo much better in THIS type of Tee instead. Try this on."

I took my daughter in law shopping for an outfit to wear to a funeral. The poor thing, bless her heart, has absolutely zero fashion sense. I spent 3 hours with her, helping her to choose peices that would flatter her figure and would be interchangable in many different outfits. By the time she was done, she was saying, "Wow, I guess I really didn't even know what looked good and what didn't!" She was thrilled. I'm sure your man will be too. :-)

ETA: In response to all the commenters who are saying that you shouldn't be trying to change him.... I help my husband pick his clothes. He was wearing pleated front dress pants (he wears dress pants and long sleeved, collared dress shirts to work every day). I helped him choose colors that flatter him, and flat front pants that look amazing on his slim frame.

I'm not trying to change him at all. He asked me for help and I'm helping. And he loves what I choose, and helping him feel good in his clothes isn't changing who he is, it's making him feel better about how he looks.

Did he ask you because he really wants to know or did he ask you out of frustration because of all your not so subtle hints?

Do you honestly believe that constantly complimenting only very specific clothes is subtle?

Let the poor man be comfortable and stop making him worry about his clothes.

I mean cheese and crackers you bought him jeans to wear! Control freak much?

Oh and fitted jeans are gay unless you are in your 20s.

Go on a shopping date. Get him to try on some shirts/outfits that you think look great on him. Say "Wow! You look GREAT in that!! After seeing you in that, babe/honey/sweetie/whatever, you gotta lose those Hollister shirts - THIS is the look for you! Fantastic!" Then buy him a couple of those shirts to go with the jeans you already bought him.

Repeat with shoe shopping.

Meh. Guys tend to be clueless about this stuff. Truly. When I met my husband, he was always well-dressed, but only because he had a personal shopper at Nordstrom, and she would call him about once per month and tell him to come buy clothes, bless her. Well, fast forward 15 years, and the personal shopper retired about 10 years ago, so my husband's closet is a mess. The only solution has been for me to buy all of his clothes for him. I had to drag him to the mall and force him to buy shoes as well (I would have just bought those, too, but he's kind of picky about how his shoes feel on his feet, so...).

Luckily, since I've been with my husband for so long, I feel free to say, "Sweetie, I need to throw that shirt out. It is stained, ripped, and makes you look homeless." Or, "I think those jeans have seen better days. Here, wear these instead." Or, "The white socks make you look like you're going to a Star Trek convention, honey. Here, wear these dark blue ones instead." My husband does not take offense. He knows he has no fashion sense. He just wears what I tell him to wear, and it seems to make no difference to him whatsoever.

I think you just need to be blunt, but kind, and tell him exactly what you think. Men don't take this kind of thing to heart.

You are right, we all like certain styles, especially on someone we are dating.

I think you are in the middle of a divorce from a jerk who cheated on you left and right, why blow it with this guy; your'e giving him a complex. He's gonna get tired of feeling like he can't please you with his clothing.

Stop complimenting him on his clothes and his physique and compliment him on how happy you are to be in his company.

Most men need help in the fashion department, it takes time to change that, just enjoy him right now and make changes later.

he's not the one for you. You're trying to change him to meet your "standards". Just be friends with him and stop trying to change who he is. that's what I would do.

Buy him a few age appropriate t-shirts for him. Tell him to dress his age, not his son's age.

When I first met my husband he had an alarming array of Bill Cosby sweaters and fleece zip-up vests. I have a sarcastic personality and like to poke fun at those who I actually really love. Knowing this, he was fine with me poking fun at his wardrobe. I eventually asked him if I could help him update his closet to a wardrobe more fitting of his career path. He was happy to oblige and he never looked back.

I think you're off to a great start! One step at a time. You should def buy him a bunch of shirts, saying, I noticed you kept borrowing your son's shirts, I know most teens would hate that! so I got you some great T's of your own! It sounds like he's trying to dress to please you and not sure how!
I assume he has stopped wearing the "mom jeans" ? the next step would be to collect some of your old clothes and tell him you heard the salvation army needed donations. You're going to make a trip so would he like to thin out his closet and you'll deliver ?
at most you can say, I hope you dont think I'm trying to change you too much just cuz I want to dress you up all sexy and handsome and show you off!

I had to marry my fashion-and-color-challenged geek. :-) Just complimenting his occasional, accidental okay outfits didn't get me anywhere.

Since we share a closet, I gradually gave away all his old clothes and replaced them with more flattering clothes. We're low-income, so my replacements mostly came from the thrift shop, carefully curated. He's still a geek, and we both dress pretty casually (in what I've heard called the West Coast or Oregon style), but all his clothes go together.

It just occurred to me that high fashion is something we seldom see in our locale. Somebody dressed in expensive, high-fashion clothing here looks rather odd. But I have to agree, tucked-in polos swing way too far in the wrong direction.

Guess you are more interested in what is on the outside than the inside. Break it off now. You cannot change him. He is who he is. Accept hi. Or walk away.

I buy my DH things I like to see him in. And then I compliment him all over the place when he does. "Oh, hon, that blue shirt looks great on you! Really brings out your eyes."

Or you could say, "I'd like to go to x restaurant. I really liked x outfit when we were at that place before. Could you wear that again?"

ETA: and if it's specifically the Hollister shirts, next time he's in one, ask him if he wants your opinion on his outfit. And then say, "I think you look better when you're not borrowing shirts from your son. Would you like to go shopping for something that's just for you?"

once he is spiffed up, what else will you want to change about him???

personally I wouldn't say anything but it would be a deal breaker if it was as important as it seems to you.

I wouldn't. Adults don't tell other adults how they should dress. I'm married to a guy who us hopelessly out of style and it's ok. He's a big boy who gets to choose his own clothes. Sorry but you aren't the boss of your boyfriend's closet.

I am of two minds on this one.
On the one hand I would say to just back off. Let him wear what he wants to wear! maybe he doesn't like your skirts, shirts, shoes, stockings, but he's not saying anything to you because they are YOUR fashion choices. Let him make his own choices on what to wear.
BUT, if he came to me and said, "what do you think of this shirt?" and I thought it was hideous I would SAY, "Bleh. I think that's hideous." I am blunt like that.
Once you guys get naked though, everything looks right, right? AND THAT is the important thing!
L.

Oh boy I totally see what you're saying and don't think you're superficial. It's the kind of thing where if you were in a long-term relationship or if he were just a friend you could just be blunt. My oldest son works for a guy I dated in high school so we're old friends. He's generally a horrible dresser in general (granted I only see him when dropping off my son for work) but he has a hideous tie-dye t-shirt (ugh really? at age 40?) that I just came right out and told him that he should burn. He laughed and wears it anyway. I tried...

Anyway...I think it's worth saying "since you asked me for fashion advice before, I have to say that I love you in a t-shirt but Hollister is a bit "young" on us middle agers. Kind of like if I were wearing Victoria's Secret Pink shirts or some other brand that your students wear, know what I mean (of course he won't know what you mean and would probably think that's hot LOL)?" and see how that goes. But it's a tough conversation to have without seeming superficial.

Good luck!

ETA: in response to Fuzzy, normally I would agree but he *asked* he for help and probably wears the darn t-shirts because he thinks she likes them! That just has to be nipped in the bud. I had a boyfriend in college who came from the suburban white-trash nightmare of a town I grew up in and I had to completely re-dress him because he didn't know better than to not go around sporting a mullet and acid wash jeans and concert t-shirts...in the mid-1990's...it's all he knew! It's OK to help people who need some updating and are open to it, it just has to be done delicately.

Well since he did previously ask, I would just say something like look, there is no tactful way of saying this so I'm just going to come out with it...you gotta stop wearing Hollister. It isn't a brand made for we ancient 40 something's. How about I come over sometime and go through your things (go shopping, whatever) and help you update your wardrobe.

Your question made me giggle as I was eating my dinner. :P

I think I would prefer the blousy polos and mom pants to the tees with the big Hollister name across the front. Oh my gosh.

That being said, there's something mildly offensive (not that you're doing it per se) about one adult's efforts to change another. You either have to take him as he is or cut him loose.

My husband is still in the polo, jeans and belt look that he's worn all the years I've known him. Sometimes I will tease him about his "holey" t-shirts but otherwise I just accept him for the great guy that he is.

FWIW I'm really tired of skin tight clothes on women and men. I wish those looks would go out of style!

I do draw the line at the Hollister shirts. :)

Tough one to navigate. Thankfully my hubs knows he has a hard time picking clothes that are flattering to him, and accepts my fashion input, within certain perameters. He has some deep seated fashion notions, which are based on his English upbringing. i.e. he doesn't think that striped ties are appropriate for grown men, as those are school boy ties. Most of America could care less, but hey, if that is a touchy point for him, I can oblige him.

I'd bite my tongue if I were you, for the time being.

Best,
F. B.

I wouldn't because I have quickly realized that my husband just...doesn't give a sh*t about fashion lol. But I also know that he would never step into a hollister store or even wear one. So I am lucky there. But usually as long as it fits right he doesn't care.

Now in your case it's different because the guy asked you I would gently direct him into stores more his age

I don't have any advice. I just wanted to say that I totally get it. You are not being superficial; I had the same issue with my husband when we were first dating and I still married him despite his terrible choice of shoes and musty overcoat, lol! Oh, your post sure made me laugh!

Take him shopping. Let him choose some clothes and you choose some that you feel will look better on him. Find a nice way to explain why this style is better with his body type than that style.

I would take him on a shopping date and buy him some items he tries on that you love. I bet he will welcome it! I wouldn't be negative about his current wardrobe though. No need to point it out. My husband loves it when we go on shopping dates and try on stuff for each other. It's so much easier to pick out clothes when you get immediate feedback from someone who knows what looks best on you.

Are you serious? He needs to run. You might be nice and all, but HELLO.

If you are serious about him and see a future with this man, offer to take him shopping for his birthday, Valentines Day or whatever. Let him know how much fun you'd have choosing clothes for him. It sounds like he's game. And continue throughout the year to gift clothes to him that you'd like to see him in.

I didn't know a thing about car maintenance or power tools when I met my husband, and he didn't know that cargo pants with pleats were a no-go. Ten years and two kids later, we are a happy family with fitted pants and purring cars. You can do this. :)

If he really needs help then he'll ask you to go clothes shopping with him, clean out his closet and then will listen and act on your advice.
As it stands right now, I don't think he's all that interested in changing.
If it bugs you that much and can't accept him as he is no matter what he wears, back off from the friendship else you'll end up nagging him to death and he's going to break it off.
To some guys clothes just don't mean that much.

Personally, I wouldn't say anything. My husband does the same thing... Any time we go somewhere he wants to look nice, he busts out his black Stetson. It wouldn't be a problem, but for some reason he gets it shaped so that it is practically flat, with barely a touch of curve to the brim... Which looks AWFUL with his head shape. :/ I usually just smile and tell him he looks nice. Lol.

For your guy, I would get him to go shopping with you... Then point out things you think would look nice on him. (Heck, go grocery shopping at Walmart, and cut through the clothing department and point out the plain t-shirt style you favor.)

Bless his heart for trying though! Lol.

when the relationship turns very serious, then you can say btw lay off holster for…ever, bootcut or straight jeans from now on, and for god's sakes no white socks with dress shoes. not now though.

Lol A. J!!!
Loved the descriptions.
So many men underestimate the importance if a solid pant/shoe combo!

I might...might not.
But if you ever cohabit -- an unfortunate clothing incident might be your best friend!

Maybe point out that the shirts that don't have fuzzy letters on them show off his physique more and you really appreciate the "uninterrupted" view.

I would leave it for now, and when you get serious you can slowly rotate those tees you don't like to the bottom drawer. :)

Good luck and enjoy the new guy without worrying about what he is wearing so much. If he is a high school teacher he is used to seeing the "preppy" kids wearing these types of shirts. And, they look cool. You can change the paper after you buy the present so to speak.

I just wanted to say I love your response to Julie S. about fitted jeans :) The only other thing I have to offer is maybe as a gift for an upcoming holiday or birthday, offer to do a mini shopping spree since you are an ex fashion industry worker. Tell him it will be fun for you to do together.

I understand where you are coming from. My husband had some wardrobe issues when we met and slowly I bought him clothes to replace the old outdated items. His issue was that he didn't like to shop. He also didn't know where to shop for clothes that fit him since he is so tall. He would rather wear outdated clothes than take the time to go shopping. But he is grateful for me to shop for him and find clothes he likes in his size.

It wasn't about changing him. I'm a better shopper and have more fashion sense. It doesn't mean I'm shallow or didn't appreciate all the wonderful things about him. I need direction in certain areas from my husband. We help each other out in areas of weakness and that makes us stronger together. One area just happens to involve his clothes. What's the big deal? (That last part was for some of the commenters)

Leave him alone. Don't force your spence of fashion on him. Who is to say that he does not feel the same about your style. Love him for who he is and stop trying to change him.

Some people do not like to spend a lot on clothes. You can send him the article on the 49ers coach shopping at Walmart for his pleated khakis (the wife is interview and is horrified about the pants). This could backfire on you since this coach obviously can afford more expensive clothes and he has a nice body. Your boyfriend might have the attitude Heck if he can do it, so can all other men.
http://www.nfl.com/news/story/0ap2000000313370/article/ji...

You can advice him to google the Hollister demographic (here I did it for you): Hollister primarily targets the 14 to 18 year old demographic; however it sells to people aged mainly 12 to 27. I would not be so bold in real life. I would make a comment that "I like to shop at X because the clothes are my style." or "Y store section is very teeny bopper for me, so I do not shop there."

Would you be willing to take him shopping and spend $300 on him for a mature outfit?