How To Get Your Boyfriend To Dress Better (15 Sneaky Ways)

There are two types of men, the ones who care about fashion and those who don’t. And by that, I really mean personal style. 

Some guys are pretty specific about what they are seen putting on, even on a quick run to the grocery store. Then there are the other guys, who wouldn’t mind rotating the same three pairs of t-shirts and jeans if you let them.

Don’t get me wrong, everyone has their vision of what makes sense on their body, we all just don’t care about it equally. You see, a guy in the latter category mostly dresses for comfort and not much else. 

If it fits and doesn’t make him look out of place where he needs to be, then it works. You are not likely to fall in love with him for his impeccable fashion sense.

Which is funny that I should mention love because did you know you can leverage your boyfriend’s soft spot for you to get him to improve his sartorial choices? You may not be able to change a man, but you can do something about his clothes/looks, and all without hurting his feelings too, stay with me.

15 Ways To Get Your Boyfriend To Dress Better

1. Understand why he dresses the way he does

understand why he dresses the way he does

Someone once said you cannot love or hate something unless you first understand it. Why does your boyfriend favor t-shirts, baggy jeans, and a pair of slides, do you know? Is he really averse to a sharply tailored suit with pocket squares and dress shoes, or is he afraid he wouldn’t kill the fit?

Asides from insecurity, some people find it hard to evolve from the first fashion sense they imprint upon. Then there is comfort, which is the most crucial factor when it comes to style for men. If you can find out what his motivations are, then you’ll know exactly what to focus on during this little project.

2. You’re trying to “fix” his wardrobe, not him

It’s no fun to see your husband/boyfriend pull up in an unflattering outfit. That’s if you can even call that terrible shirt and pants an outfit. But, the potential embarrassment you fear isn’t enough reason to make a whole man feel like crap. You need to remind yourself that at the end of the day, it’s just clothes.

You don’t want to give him the sense you are trying to make him into who isn’t, as that would only make him feel like his real self isn’t enough. So it’s best to come to terms with his personality and accept it as what you have to work with. If you must criticize, keep it strictly about the clothes or shoes and, more importantly, do it gently.

3. Convince him to go shopping with you

What are the chances of your man going on a shopping trip with you? If there is even a slim chance of that happening, you can make a date out of it. You might make him think he’s only taking his girlfriend out and while you are there, suggest some things for him to try on.

It can be a good way to switch things up in your relationship, too, so he’d probably agree with you even if he usually wouldn’t pick a fashion/clothing store.

4. Get him some more clothes just because

You can also take matters into your own hands once you know his size and a fair idea of what would look good on him. Nothing too crazy like a box load of clothes and shoes, though, so it’s not too overt that you are trying to change his wardrobe.

It could be a good pair of socks today, some quality pants the next time. If he asks why tell him it’s because you love him. Or that you saw them and thought they’d look great on him.

5. Stay as close as possible to his personal preference

stay as close as possible to his personal preference

Based on this survey, men also dread dressing up in the morning because they can’t decide on what to wear. And that’s probably with clothes they picked out themselves. Don’t give your boyfriend any more reason to avoid his wardrobe by picking out items that scream you rather than him.

Make sure your ‘random’ gifts match what he even sees as good and would be comfortable wearing. In other words, consider his style and personality first and foremost. Otherwise, he may not be as eager as you’d like to put them on.

6. Show him what you like

As his girlfriend, you are in a unique position to influence your man’s fashion taste without saying a word. There’s fashion everywhere around us these days, thanks to tech, so you can leverage that.

Instead of overtly criticizing his wardrobe and outrightly coming out to tell him his style is wack, you can show what you dig instead. Scrolling social media and you see a male fit you like? Send it to him. If he approves, you can get him something similar, and if he doesn’t, ask him what he doesn’t like about it, and you can meet each other in the middle.

7. Remember less is more

When you are trying to help someone, no matter what your relationship with them, always remember that less is more. Be careful not to come on too strong, as if his current dress sense is the literal worst (even if it is).

Whether it’s convincing him to see the good in a style, or getting him to consider other types of pants besides jeans, let him go at his pace. It’s how you make sure he doesn’t get overwhelmed along the way and give up.

8. Draw his attention to the details

Like most men, maybe your partner’s issue is that he doesn’t care much for colors. Perhaps it’s that your own never seems to get his choice of shoes right. Or that his shirts never fit. And these details make a huge difference.

Some outfits are great the way he already wears them, they just need a little accessory to spruce them up. So you can bring his attention to these little things, and if he looks in the mirror and likes what he sees, he just might get gingered to do more.

9. Give tips on how he can make a good fit better

Sometimes the problem isn’t that they don’t want to look good, it’s that they do not know how. You can make it look like you are bouncing some ideas off him while he’s dressing up just to see if they work. 

They might be as minor as asking him to add a button-down to the usual t-shirt or change his socks or even his belt color. Thankfully, you don’t have to be a professional stylist to know what tips to give, just be an extra set of eyes who love him enough to care.

10. Pick out his clothing

One easy answer to how to get your boyfriend to dress better is to do it yourself. Cut out the back and forth and just take matters into your own hands. Of all the tips, this may well be the least frustrating overall if you can look past the dependence.

Get him to agree to a wardrobe overhaul or at least some modifications, and then go shopping. You certainly wouldn’t be the first girlfriend/wife to do this, and it saves everyone a lot of time and energy, so it’s a win-win.

11. Dress to impress yourself

dress to impress yourself

Another way to get your man to up his style game is to improve your own first. Trust me, no matter how much he appears not to care about his look, he’ll want to make an effort when he starts looking inferior to his girl. He wouldn’t see you looking at your best and feel confident following you in shabby clothing.

12. Give him a reason to dress up

First, you give him a reason to want to dress up (#11), then another one to do it. After all, you’re not doing all this (from reading tips to shopping) so the good clothes can sit in his wardrobe. If his lifestyle doesn’t give him any reason to get out of his comfort zone, you may have to create some.

Ask him to come with you to work and family events, pick locations that force him to change to change out of the casuals for dates, etc. Then inform him of the dress code, and I’m sure he wouldn’t want to disappoint you or himself.

13. Make use of positive reinforcement

In other words, gas your man up! When he finally starts taking your advice, appreciate him. If he looks good wearing one of the clothes you pick up for him on your shopping trips, let him know he looks good, so he feels confident to try even more.

If you’re trying to get him to try colors out, for instance, pay him compliments like they match his eyes or hair or skin. Make sure you are not lying, though, because other people will see him, and if the majority of the comments negate yours, he may not stop taking style advice from you.

14. Teach him to fish

teach him to fish

You know what they say, teach a man to fish, and you feed for a day, but if he learns to catch them by himself, he gets to eat for a lifetime. 

While there is no harm in being his personal stylist, educating your boyfriend on how to dress and improve his style takes the stress off of you and empowers him to stay independent. It also gives his individuality room to come out to play, which is a good thing.

Give him tips on the basics he should at least have in his wardrobe, from a t-shirt to suit to shoes to jackets and sweaters, depending on where he lives. You can also put your boyfriend on your clothing plug instead of doing the shopping for him. Once you get him to a stage where he starts picking decent clothes and paying for them by himself, you’ve just about done your job. 

15. Out with the old, in with the new

And finally, gradually begin the process of purging his wardrobe of his old stuff. Get him to discard the worn-out suit (or suits) when the new one comes in, as well as those favorite clothes (those poor jeans) that tend to suffer the most.

I wouldn’t throw away his clothes behind this back (relationships have ended for less), but you can encourage him to box items that no longer fit up for charity. Anything can be fun when you do it as a couple, even spring cleaning.


How should a man dress better?

Dressing well for a man just about the clothes but also how you choose to style them. He should pay attention to details like prints, colors, and accessories, as well as the occasion. Not all events call for a three-piece suit but throwing a jacket on a t-shirt and a pair of jeans does it can change a look from basic to stylish.

Is it OK for your boyfriend to tell you what to wear?

It depends on how close you are to your boyfriend and also his reason for doing it. If he’s trying to be romantic by picking out an outfit for you, there’s nothing wrong with that. But if he leaves no room for your choice and forces his opinion on you, that is not ok.

What outfits are guys most attracted to?

Guys are attracted to clothing and accessories that accentuate your features, from dresses to jewelry. Therefore, they may be partial to form-fitting outfits and those that require you to wear heels and colors that complement you.

How can a guy look rich and classy?

To get a man to look classy, he should steer clear of bling, especially if he has no way of knowing which is original. For clothing, he should stick to well-tailored outfits that fit him. For accessories, less is more. More importantly, he should learn to polish his shoes and keep his clothes always neat.

What things make a guy attractive?

A man with an impeccable sense of style can be pretty hard to resist. Besides clothing and all things fashion, however, other features people find attractive in a man include voice, confidence, kindness, charm, empathy, sex appeal, etc.

To Conclude

With a little nudge and positive reinforcement, you can help your boyfriend or husband reach his full sartorial potential. You will need a bit of patience, too, because the change you want won’t come in one day. 

Don’t forget to work with his preferred style/personality and to let much of the changes be his choice; otherwise, they may not stick. With that said, please let me know in the comments if you found this helpful and share it with a friend who might need it for her boyfriend. 

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