Off The Cuff: How Can I Make My Boyfriend Dress Better?

Dear Winona,

My fashion question isn’t about me, it’s about my boyfriend. He dresses . . . how should I put this? . . . like a huge slob. I always hint that he should try to look a little nicer but he doesn’t take me seriously. Sometimes his style (or lack thereof) embarrasses me. I fantasize about throwing away all of his cutoff T-shirts and crusty basketball shorts. Is there any way to get through to him? Help!

-Embarrassed girlfriend of the guy wearing pajama pants at Home Depot

Dear EGOTGWPPAHD (now that’s an acronym that just slides off the tongue, isn’t it?),

This is a touchy topic for sure. Obviously you love your boyfriend for reasons other than his outward appearance, but that doesn’t mean you don’t want him to look nice and dress in a way that’s attractive, appropriate, and, um, regularly laundered. There are ways to get your point across here, but you have to be very tactful (like diplomat-to-an-unstable-country-on-the-brink-of-a-revolution tactful). Keeping that in mind, here are some guidelines for gently nudging your boyfriend toward an improved sense of style. Here's what you can do:

Encourage him.

Positive reinforcement is the name of the game here. Whenever your boyfriend gets it right, style-wise, be sure to let him know...effusively. Tell him how great he looks. Be genuine, of course, but feel free to lay it on a bit thick. If you act like he’s a freshly-oiled Channing Tatum every time he puts on a clean shirt, chances are he’s going to wear clean shirts more often. Is it a teeny-tiny bit manipulative? Maybe, but as my Italian grandmother always says, “Manipulation is fine if you do it out of love.”

Ask honest questions about his style.

I’m not talking about judgy, leading questions like, “You’re wearing THAT?” I’m talking about thoughtful, honest questions that actually help you understand him and his clothing preferences. In a non-stressful moment (i.e. not when you’re getting ready for a formal event and he still has his college hoodie on), ask him genuine questions like, “What draws you to certain clothing?” or “When do you feel most confident? Does your clothing ever affect the way you feel?” or “Is there anyone whose style you admire?” Be open to his answers, really listen, and see where this conversations leads. You’ll probably learn a lot about why he dresses the way he does. Does he truly not care about fashion? Is he overwhelmed by the idea of trying to find a personal style? Does he hate shopping so much that he just reverts to the same thing he’s been wearing since high school?

Help. A little. And only if he wants it.

So let’s say some of those questions lead to the revelation that your boyfriend wants to dress better but despises shopping. Let’s say you really enjoy shopping. Ask if he would be open to you doing a little personal shopping for him and seeing if he likes any of the stuff you pick out. If he’s open to it, great! Have fun! Get him some dapper new duds! But if he’s not into it, you must respect that.

Pick your battles.

If he’s standing by the front door in marinara-stained sweats saying “Hurry up, I’m ready” on your best friend’s wedding day, that’s obviously a huge problem that you need to discuss with him. But when it comes to his outfit choices for those Home Depot trips, hanging out with friends, or doing chores around the house, you’ve got to let it go. The fact of the matter is your boyfriend doesn’t care about fashion and prefers to keep it very (very, very) casual. You have to make the decision to be OK with that, at least most of the time. If there’s a special occasion where his clothing choice could be seen as disrespectful, and/or it would mean a lot to you for him to dress better, then by all means be honest with him. But the other 90% of the time? Let him rock those pajama pants, if that’s what he wants.

On the other hand, here's what you definitely should not do:

Micromanage his wardrobe.

Don’t get in the habit of laying out outfits for him every night. Don’t throw away his favorite ripped, stained T-shirt. Don’t organize his closet according to the items you like best. Respect him and your own time enough to keep some healthy boundaries in place between you and his wardrobe choices. He’s an adult. He gets to dress himself every day. It’s one of the perks.

Be mean/cruel.

Mean comments about his looks, even said in a jokey tone, are 100% not OK. Imagine how awful you’d feel if the tables were turned and your boyfriend made rude or sarcastic comments about your clothing choices. There are ways to broach this subject in a loving, respectful way. Saying “Oh great, you’re wearing those sexy basketball shorts again” is most definitely not one of them.

Have a fashion or style question? Email Winona at and she might answer it in a future “Off The Cuff” column!

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