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.
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 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.
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.
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 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?
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!
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.
I like Peg’s suggestion… go very slowly. You don’t want to embarrass the guy. He is trying to impress you, and it sounds like you are being fairly deliberate in your hinting, but do take it carefully, "those Hollister shirts are all right, and I think you would look great in… (Be sure to use the “and” instead of “but”; one is inclusive and one is exclusive, if you understand my meaning.)
Years ago, I got a haircut. The stylist said the worst thing he could have at the end: “Doesn’t your hair look SO much better!?” Which was sort of a backhanded compliment of his own work. You want to avoid that “so much better”… just “WOW! You look fantastic in that (new/better) choice” will convey your approval. And know that if you are acting embarrassed when he goes out with what he is thinking is “cool”, it’s going to hurt his feelings. He wants you to like him for just him, regardless of what he’s wearing. At least, that’s how I hope my husband feels about me when he sees me in my flannel checked pj pants and an old tee-shirt in the evenings and in the morning. 
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.
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.
Your question made me giggle as I was eating my dinner. 
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.
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.
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.
If you can’t accept someone for who they are then you need to move on. A human being is not a “fixer upper” into what you want them to be.
You’re being passive aggressive with your “hints”. Now you don’t like the direction those hints are steering him. If he truly asked for help then just tell him, straight up. If you only think he asked when he very well may not have then let it be. Accept him for him and move on.
I can think of a million more worse things than I don’t like the t-shirt he’s wearing to be worrying about. If he’s a good and decent person that you enjoy spending time with, that’s what is important, not if he’s wearing a tshirt you don’t like.
As for what you should wear based on your age. That’s all a load of made up crap. A person should wear what they like, feel comfortable in and what they enjoy wearing. If a 40 something wants to wear a Hollister tee that is their choice and right. I personally think anything that has the shop’s logo sprawled across your chest looks stupid on any age. Great, you’re showing off that you spent too much on a stupid tshirt, good for you. But if someone wants to I certainly am not going to tell them to stop doing it. That shirt doesn’t change who the person is at heart.
I wouldn’t say anything. I will compliment someone if I think they look especially nice because it’s a nice thing to do. But I don’t feel the need to tear apart everything a person wears in an effort to change them into something I think they should be.
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.
Are you serious? He needs to run. You might be nice and all, but HELLO.
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.
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!
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.