How Men Can Dress Sexy

What is the "sundress for men?" I found out.

One of my first articles on this Substack was about clothes men like and don’t like on women. At the time, I had to be really careful not to be too prescriptive because women would inevitably get annoyed that they were being told how to better appeal to the male gaze, as if they don’t hear that often enough from men. Perhaps women are sick of their looks being under the microscope, and millennial women in particular are probably still reeling from seeing stuff like this throughout their formative years:

But men are a bit different. Perhaps it’s the fact that their looks are focused on so little that they don’t really get much helpful (shallow) advice, beyond “hit the gym” or “it’s so over for small-handcels.” And a lot of men just straight up don’t know how to dress at all, let alone how to dress to appeal to straight women. Men don’t even really get feedback on their clothes from other men, let alone women. While a woman can wear an outfit and receive compliments from all her female friends, guys generally don’t do this (at least not as often as they should- you heard it here first, men. You should be gassing each other up.)

Don’t get me wrong—if a man loves fashion there are places he can go to learn more about it, most notoriously, Menswear Guy on Twitter. But while Menswear Guy knows just about every menswear rule there is to know, and has fantastic taste, his fashion guidelines are mostly about following the very strict rules of menswear, particularly suiting (rules which I’d say fewer than 5% of people even understand) and although following his rules might have overlap with “looking attractive to women,” it’s not his focus.

I’ve also had several men in my DMs or replies asking me for fashion advice from a female POV. I don’t DM very often, so I haven’t been able to help them as much as they would probably like, but these DMs taught me that there is an unmet need for straightforward “how to look attractive” fashion advice for everyday men. These men don’t just want to know whether it’s appropriate to cuff pants while wearing square-toed shoes a la Menswear Guy’s feed (although that advice is still lovely to have.) They want the quick and dirty: what can I wear to look sexy to women?

So I started a Twitter thread to ask women who are attracted to men: what kind of clothes do you like men to wear? What kind of clothes do you find unappealing?

A few exciting things about this article:

1. Most of the stuff that got the most positive female attention was easily attainable.

2. More good news- I’m going to give you links (some fairly affordable, some aspirational) where you can buy this stuff.

3. Wherever possible, I’m using real photos of real men, not just celebrities. I selected photos specifically based on what mirrored points from the article, so there were a lot of great pics that I didn’t use- don’t take it personally!

4. I’ll also let you know what women have told me they really don’t like.

5. Even better—there are some tips for ways to style items you already own that will boost your attractiveness.

Of course, I should preface all this with two things. First, most of the women I spoke with were white, in their 20s to 40s, and middle class to upper middle class. That wasn’t by design; that’s just who responded. So obviously there’s some degree of bias, but it probably works with who I know my male readerbase is anyway. You’ll also notice that most men who provided photos were in the same basic demographic. Again, I didn’t discriminate based on appearance or attributes for these photos—I did, however, only select photos that worked with the tips in the article.

Second, I know some folks will say that all this fashion stuff is pointless if you aren’t hot. Obviously hot people get away with more than not-hot people do, and hot people are going to appeal to more people than not-hot people. But not everyone can be hot, and people who aren’t hot find each other attractive and fall in love all the time, so there’s still something to be gained from dressing nicely. Personally, it’s my view that nobody is truly “ugly.” If you have good hygiene, take decent care of yourself, and dress well, you’re probably at least average in the grand scheme of things. So while I’m by no means advertising these clothing tips as instant “Chaddification,” you can at least mog your former self—no mewing required.

So let’s get into it.

1.) Your clothes should be tighter.

This is obviously dependent on the style of the outfit (skintight jeans were a turnoff for many women, as were gaping button down shirts) but most men simply wear clothes that are too big for them. I think this is more of an issue for skinny guys than bigger guys, but clothes that skim the body generally appear more stylish than baggy clothes. Per a female follower:

So, some things shouldn’t be too tight, but there are lots of other things that men could stand to wear a bit slimmer.

If you have a particular aesthetic that involves baggy clothes, that’s obviously different, but I feel like most men reading this are guys who don’t have a defined aesthetic already and just want to appear more attractive. The below images are actually from a female reader who wanted to show some appreciation for her husband’s style (I agree, he looks great.) See how he has a slim build but doesn’t overwhelm his body in baggy clothes? He’s not wearing skintight clothes either, but he’s following his overall shape:

I like this one because he’s doing a lot (mixing patterns, bringing loden green corduroy into an outfit that looks like it’s “supposed” to be blue and white) and yet it kind of works because it just fits well. Take notes:

Men should consider opting for slim or straight leg pants, as opposed to skinny or baggy. It’s also important to correctly measure your inseam, waist and hips to make sure that the pants fit you well. “Invest” in a flexible tape measure, it’ll help.

Now, my husband is absolutely not a dress pants guy at all- he lives in either straight leg jeans or sweatpants—but when he had to buy dress pants for a wedding he loved these, and they look great on him: