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How to Makeover Your Man (With His Help!)

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If the man you love has a good heart but terrible style and you want to see it improve without causing a rift in the relationship well then, this post is for you! It’s time to…makeover your man!

I’ve shared a bit about Titus’ makeover journey on my Instagram stories (also- if you want daily life tidbits you’ve got to follow me there!) and many of you reached out with your own stories (and same frustrations haha) about how to go about improving your man’s style.

This topic can always be a little tricky, but just so it’s clear, Titus wanted to do this makeover with me. It was of course, originally my idea, haha, but I wouldn’t have “forced” him into anything. It was ultimately my goal to find clothes and a hairstyle that we BOTH like. I also don’t promote manipulating or tricking- just lots of patience and encouragement. 🙂

So what brought this makeover on?

Well, it’s been about 10 years in the making haha. When I met him 10 years ago he was graduating high school and working on a farm. His wardrobe consisted of dirty gym shorts, torn apart sneakers, carpenter jeans, and old t-shirts. Well, he ditched the jeans in college, but that was still the majority of his look- up until…hmm…a couple of months ago haha.

We were randomly just driving somewhere when I turned to him and asked, “Hey, so do you think you’d want to do a makeover now?” To which he replied…


Gasssppp! I truly was not expecting that because we’ve gone back and forth about that for years.

Tip #1- Don’t just bring it up once and be done (but don’t nag either). Chances are, he’ll never come to you and say he wants a new look, but there may be one time that you ask and he finally agrees.

I clarified that he truly was all in and then I got to it. Right away.

Tip #2- Don’t force it! That can never end well. Wait until he’s ready.

Makeover Your Man: The Hair

One google search later (I searched “men’s hairstyles”) and we compromised and found a hairstyle that we both liked. I leaned more towards the comb-over (which he calls “The Bachelor” hairstyle haha) but he was not a fan of that, so we scaled it down. But what we ended up suited him way better!

inspiration below

mens haircut inspiration



Tip #3- Try to keep his lifestyle, wants, style, and needs in mind when choosing a new look. Just because something works on a Bachelor contestant in LA doesn’t mean it will necessarily work for a simple midwesterner…if you get what I mean.

Tip #4- The right hairstyle is a GAMECHANGER. It can totally transform anyone (girl or boy). Start with the hair first to get an idea of “style” before you move to the clothes.

I was honestly shocked when I saw him after his fresh new hair cut. It made him look younger yet more mature all at the same time. I was very pleased and the best part is? So was he! It didn’t hurt that I told him how much I liked it either. 😉

Tip #5- Positive reinforcement is *key*. What man doesn’t want to hear from his s/o that he looks good? Constantly tell him how much you like it when he wears ___ or styles his hair a certain way. But of course, be genuine about it, and I can almost guarantee that your man will want to do more of whatever it is you like.

Makeover Your Man: The Clothes

When starting over with his wardrobe, I followed the same type of process that I cover in my ebook. We took everything out, went through item by item, made donate and toss piles, and made a list of what we needed.

*For the ladies- My ebook goes into a LOT more detail about this FYI. Perfect for women that are wanting to get a makeover themselves and start over with their wardrobe!*

After finding the holes in his wardrobe and asking Titus what he wants to be (he said “comfy” haha), I had a good idea of what we needed- elevated casual wear and clothes that looked nicer without feeling stiff or restrictive.

We pretty much got his whole wardrobe at Walmart btw (not sponsored). I didn’t plan for that to happen but wherever we shopped, Titus said it had to be affordable (he hates spending money on himself) and we struck gold at Walmart with a few things, so we kept coming back. I’m going to share the specific things we got that are worth buying- they’re all comfy (Titus’ #1 request AND cute (my request)!

These pocket tees are fabulous! We got them in multiple colors. They’re super affordable and the material looks nicer than your average t-shirt, but they feel just as comfortable…if not more. And I know this because I got some of these men’s shirts for myself too haha! I wear them with biker shorts and/or as a dress.

Super big fan of these terry shorts (options are limited as of now, sorry). Comfy (of course) but they look way more elevated than gym shorts! He has them in black and charcoal gray.

Titus really likes the materials of silky polos but I’m not the biggest fan of the style. The compromise? These tops! I like them better than polos and they feel the same in Titus’ eyes. He has the yellow one. I don’t force my love of neutrals on everyone. 😉

Speaking of color…Titus got the green juniper pair of these shorts. He likes color so it’s nice to have this pair for summer that still looks grown-up.

These jogger shorts are a really good buy. I like the slimmer look without cargo pockets and the length that hits above the knee. He has them in khaki and gray.

It’s always good to inject a little bit of personality into your wardrobe! Titus picked out some Hawaiian inspired shirts and loves them, especially this one.

Tip #6- Let your man pick out things that they want too. Their wardrobe should show off their personal style and be something they’re excited to wear!

from our Rome trip last year

Shoes & Accessories

No wardrobe is complete without the right shoes and select accessories. Yes, even for guys! Some of these we already have and some of these we’re working on getting still, but here are the shoes and extras that I think totally add to a man’s style:

I can finally say that his summer wardrobe is goooood, but I imagine that we’ll revisit this in the fall too! I did a fall capsule wardrobe for my toddler so I get really excited thinking about this. 🙂

Did you find this helpful and do you feel ready to makeover your man? Drop me a comment below or share your own experiences in the comment section!

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makeover your man


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.