How do you politely "guide" someone's fashion choices :)

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1

OK, sort of silly and just for fun:

I'm seeing a nice guy. We don't spend much time together with busy lives, but we do see each other "regularly"-about once every week or two, and he does value my advice he says.

I'm an ex fashion worker from NYC and he's born and raised rurally with no exposure to fashion stuff. So there's a fashion chasm between us. :) When I met him, it was at a casual gathering with a mutual friend, and he was in plain jeans, regular sports tee shirt, sneakers: Perfectly CUTE!!!!! No problem! We got acquainted and went out again. It was when we went out for some "dates" that I realized he usually dresses like....he's from this area... I KNOW I'M SUPERFICIAL but don't we all find certain looks more attractive than others?

For my age range (40s), I like simple classic stuff. When in doubt, less is more. He has a nice physique, which I have complimented many times in an effort to say what flatters him: (simple untucked tees or shirts over fitted jeans with classic sneakers) vs what doesn't: (blousy dress shirts tucked into high-waisted, loose-fitting mom jeans with a big belt and big cuffs on jean legs with strange dress shoes at bottom of large leg openings and white socks showing???!!!!!)

I've tried to stick to the positives to gently steer away from negatives to spare his feelings. I have said, "I loved what you were wearing when we met, you looked so handsome". I bought him a couple of classic pairs of Levis as gifts which he wears and I've gotten him to stop tucking in his tees, but ALAS!!!! Now he's in the habit of always borrowing his teenage son's Hollister tees. He mentioned his son (16!!!??! HELLO!!) "has only Hollister in his closet because that's the only brand he likes" so that's where the endless supply is coming from I guess... I think he picks them to wear around me because he knows I like tees better than.... blousy polo shirts tucked into belted, loose, pleated slacks (THE HORROR!!! that took some fancy explaining along the lines of "I really love it when you DON'T wear your big polos and loose slacks-I can see your nice body so much better"...when it wasn't really about his body- just about avoiding the polos and pleated slacks....which I don't mind on strangers but it freaked me out on a date...)... and because the tees are tight on him (his son is very thin) and perhaps he has taken my complimenting his physique to heart. Or maybe he thinks it's an OK brand for adults??!! Or that it's fancy because it's in the mall? He's a high school teacher so maybe he's used to seeing that brand on students??

I don't know why I feel hesitant to take on this last hurdle... I feel like mentioning it in any way would be offensive..maybe because it's gone on for several months so I'm afraid he would feel weird to find out NOW that I think he's a little too old for Hollister...He's a sweet and smart and and interesting and hard-working and thoughtful guy. He has asked for fashion help, and I know he would not WANT to wear something that I was not liking...He showed up for a dinner I made last week all cleaned up with flowers and chocolate and another tight Hollister tee I hadn't seen yet (big raised felt hollister letters sewn across chest)... I'm totally at fault for even caring about this right??!!! If he wants to wear tight Hollister tees at 44 he can right? Who cares?!! Sigh.

But let's PRETEND you were going to tell someone you really like you did not prefer their certain garments....how would you say it tactfully? Is it a s simple as, "I prefer your regular miscellaneous tees to the Hollister tees"? Why am I so scared to say something? If he was my boyfriend or husband I would just say, "Quit wearing those, we're too old for hollister" and we could duke it out from there.. :)

Would you say anything ladies, and if so, how?

2

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.

3

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.

4

“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 =)

5

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

6

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.

7

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,
fanged bunny

8

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. :confused: 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.

9

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. :slight_smile:

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.

10

I had to marry my fashion-and-color-challenged geek. :slight_smile: 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.

11

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.

12

If he wears Hollister t-shirts, so what.
Here in my State, where it is full of Surfers, of ALL ages… even the “old” ones wear surf brand t-shirts and board shorts, the same brands that the young kids or college kids are wearing. Even 40+ year olds wear Volcom or Hurley t-shirts too.
There is no age, limit, to it.
It is the fashion “genre” of it etc. So what.

We recently had a repair man to our home. He was dressed in surfer type shorts, and a surfer type brand t-shirt, and he looked good. He was in his 70’s. And he looked perfectly fine in it.
And he also still surfs.
But not only surfers dress this way, in my State. Most everyone does.
Its common dress for any guy.

I dunno, I don’t dress a guy whether I was dating them or more seriously. And my Husband, well he dresses the way he dresses. I have other ideas about what he’d look good in. But its not a big deal. I don’t put my clothing preferences, on him. He is, him.
And that is fine. He looks good.
And to me, age does not matter in how a person “should” dress. Unless if they are looking like a hooker or gangster or wearing high socks with loafers or sandals. UGH.
Whatever.

Since your guy did ask you for clothing tips.
Well, I would do it in line with his own tastes.
Or maybe just update him.
Not “change” him.

And quite frankly, I would not like a guy… if he dressed only to suit me or please me.
I think that is “wimpy.”
If I don’t like the way a guy dressed, oh well!
I like the guy, anyway.
Unless of course, again, he dressed like a hooker or gangster or worse or dressed like some 70’s disco dude.

13

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.

14

It could be that the reason you’re scared to make suggestions about “improving him” is that you know it can kill a friendship. You might not want him to “improve” you!

If I were you, I wouldn’t buy the fellow any more clothing unless he really asked me to help him shop. If he asks for clothing lessons, you can give them to him - gently, a step at a time. It’s not hard, for instance, to say, while you both are shopping, that you like the look of socks matching the shoes - and, incidentally, reserving the white socks for the basketball court or the yard work.

One thing you can do is to look for what he wears now that you do like on him, and saying something about the good stuff. It might take some looking. But you might like the shoes he’s wearing. Or, even if the shirt design is awful, the color is great: “Wayne, you need to wear more of that shade of blue. It really rocks.” Look for the good things and mention those.

You need to give a whole lot of praise before you can make a single correction. Everybody is hurting inside and needs to be built up. This is a way to do it. (The trouble with saying, “I liked what you were wearing back then…” is that there’s an inferred BUT - “…but you sure are messin’ up now!”)

Do you think he’s possibly borrowing his son’s clothes because he feels old (or at least middle-aged) and this is his idea of trying to stay hip and attractive? What do you find attractive about him? It’s not his outsides, so it must be his insides. That’s great! Make a list. It’ll help you focus on the positives.

15

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.

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?

16

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.

17

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.

18

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?”

19

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!
Laura

20

Stop being so damned “gentle”.

I love for my husband to wear the suit pants that have flat front pockets. They look so good on thin physiques, and I tell him so. When he wears something that’s not my favorite, I might say nothing. When he wears something that I find to be hideous or just questionable, I question it. “Hmm, how’d you come to settle on that ensemble?”

I’m talking about my husband because it’s been a little while since I’ve been with another man. When I was dating, though, I did the same thing. Having that kind of rapport is what I needed in order to know if it was worth moving forward together. I can’t spend that kind of time with someone whom I can’t talk to. If my guy had shown up with a tight shirt, I might have said, “Hmm, that’s a tight shirt.” If you know that it’s his son’s shirt, then take the reins and set one of your dates for the store. Let him try on stuff and show him specifically what you like and ask him how he feels about those articles. He is his own person and needs to express himself like he wants, but you should be able to at least count on his clothes fitting.

Even through his blouses and skirts, you can tell that he has a nice physique? Do you have X-ray vision, or have you dabbled under those potato sacks? If the latter, then you certainly should be able to speak frankly with him about something that is your livelihood. Maybe you even say, “Curtis, I really like your body and would love to see you in certan things that I think would look super good on you, since that’s what I do. Would you mind?” “You have the kind of body that I would love to dress.” Have one big discussion and be done with it. You are putting too much energy into worrying about it. He can say either yes or no. You might even ask him how he came to have this style that he has. Let him tell you his story. It seems kinda silly to me that you two might be thinking the same thing–that he needs some wardrobe assistance–and neither wants to mention it.

PS. On the right body, a tucked polo style shirt is sexy as hell. It’s got to fit, though, and his belly can’t be big.

My husband happens to be very stylish, so this is not my issue. When I’m wondering why he’s wearing a certain tie or certain cuff links, I don’t hesitate to ask him why. All my boyfriends got that treatment, and I was prepared to get the same from them.