How To Trick Your Man Into Dressing More Masculine

Along with the different societal standards that have villainized the role of masculinity in the United States, men’s fashion has declined significantly in recent years. Cropped shirts and tight pants have taken the place of classic masculine attire, and needless to say, many of us aren’t thrilled about it.

By Alyssa Vandermeulen3 min read

If your man tends to dress on the sloppy or feminine side, you might be feeling unsure how to approach this awkward conversation. You don’t want to make him feel self-conscious, especially if he feels strongly about his fashion choices, but you also need to communicate your needs and desires for his masculine side, particularly his manly appearance. In order for you to fully tap into your femininity, your man needs to lead with his masculinity.

Like all other aspects of your relationship, communication is essential! Fashion may not even be on his radar at all, and he likely relies on the pieces already in his wardrobe to build his uniform. For starters, you can mention that you’d like to see his outfits match his masculine personality. This conversation should be fun and flirty! Supporting your guy means building up his confidence, not tearing him down.

However, this conversation looks different depending on the status of your relationship. If you’re married, you should consider the longevity of his fashion choices. Has he always dressed on the feminine side? Is this just a trendy phase or his new identity? Because you know him well, you can focus your efforts on the most effective strategy for his personality and your goals. 

On the other hand, if you’re dating and have been with your boyfriend for a while, there is a natural progression into outfit suggestions if you shop together often. This conversation is also a perfect opportunity to practice communication and to gauge his willingness to accept feedback as your boyfriend. However, if this is something that he does not want to change, you can decide if his physical appearance and fashion choices are a deal-breaker for you. 

Here are a few different ways to build upon that initial conversation and help your man dress like his most masculine self! 

Text Him Style Inspo

After you’ve had a conversation about his clothing choices, test the waters by sending him style inspo through a text or DM. Remember to focus your comments on him, though, and not the attractiveness of the man in the photo. Tell him that he would look amazing in that particular style, not that the man in the picture looks hot! You could also find his celebrity look-a-like (which is a fun couples activity) and then send him IG photos that fit his masculine style. 

If this approach doesn’t work, try sending him links to clothing pieces that would add a masculine touch to his wardrobe. Subscribe to brand emails for men’s clothing lines and show your guy the newest arrivals. Exposure is a great way to transition his current style into a more masculine version! 

Change His Social Media Algorithm 

Just as the influencers and brands you follow correspond with your aesthetic, his algorithm might be showing him the wrong fashion choices. Luckily, there’s an easy fix! Ask him if you can add a few new accounts to his social media feeds, which will organically produce more masculine clothing content in his FYP and recommended posts. This subtle change presents your man with specific content that will change his style gradually over time, on his own terms.

Gift Him Masculine Clothing

Happy birthday! Here’s a masculine shirt I think you would look great wearing! Happy anniversary! I bought you new shoes! Merry Christmas, I love the way you look in this color! 

Shopping for men is a difficult task overall, and once you’ve exhausted his hobbies as potential gift options, clothing is an easy way to influence the masculine vibe of his wardrobe. Gifts are also a fantastic way to gauge his personal style and its potential manly update. If he likes accessories, try to add new pieces to his wardrobe. If he likes a certain fabric or fit, find clothing that meets his requirements without sacrificing his masculine appearance. 

Offer Subtle Suggestions

Headed to the mall to buy new jeans? This is your opportunity to subtly suggest that a straight leg jean is a better look than his trademark skinny jeans (which have a feminine appearance). Tired of the sweatpants for every outing? Try picking out your outfits together so you aren’t overdressed and he isn’t underdressed. Vacation on the calendar? Mention a few weather-appropriate looks that you would love to see him wear. The key is the subtle suggestion, though; you don’t want to wear down his confidence or focus all of your conversations on his clothing. 

Compliment Him When He Looks Good

One of the easiest ways to encourage your man to dress more masculine is to compliment him when he does! This should be the best part of the whole process, as you grow even more attracted to your guy and his masculinity!

Give him (or text him!) flirty little compliments about his outfit and his appearance throughout the day so he knows that you have noticed his effort: “You look so good in this” or "You look so sexy in those jeans, you should wear them more often.” 

Shopping Recommendations 

Need some ideas on where to start? Here are a few items currently in our shopping carts for the men in our lives.

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