Oh, I definitely got some same face syndrome going on. And I'm forever stuck in "pretty boy/femboy" land... That aint changing any time soon. So I do approach all characters, regardless of gender, the same.
But beyond that, I think I'm half decent at making my characters look "different enough". dont think they'd pass the silhouette test. I love flowy fabrics and outfit design. Colours are super important and i think I grasp them pretty well when it comes to designing. I write vastly different (fantasy) worlds that allow me some pretty interesting potential designs. It seriously pains me when I have to simplify designs so I can realistically draw them into comics without each chapter taking a month to draw;; hah
I'll throw down some examples;



(There are 3 women total here just so you understand how bad my feminine male problem is LMAO Middle one in the first image, bottom left with the light green hair and the top right with red hair in the second image. the rest are men.)
But regardless of anything, each and every design is both made to be pretty and meaningful. There is no aspect that doesn't have some kind of explanation, in world or to the eye. And it is ALWAYS important to remember the characters around them can be used to enhance these designs. Not by drawing them side by side, or making them look good together, but in how designs can "speak" to eachother. That's easier for me to explain with explaining characters, so, humor me.
Let's take a look at Halla, the god of Death:

Well he wasn't always the god of death. He is the villain of the story, once a prince that wanted to be more than just a king he orchestrated the prior God of Death's demise and took his place. Halla is the absolute opposite of the current king (his dad which has importance to the story), who dresses in darker colours and purple. So, Halla wears lighter colours (white) and yellow/gold, opposite of the purple on the colour wheel. Long hair gives a sense of timelessness, though that is false. Dude's a teen. He's someone full of lies, so why wouldn't his hair also lie? I mean, the heavenly colours are kind of a huge lie too, dude ain't good. He's committing genocide. The pink jewelry is just a sign of decay in this world, rot is sickly sweet and visceral, but not was alive as other colours like, say, red. The gold in his jewelry not just fit the colour scheme he has, but also gives him a look of status.
So when we look at his high priest, Alvah who basically is nothing but feeding off other designs to get to know him:

We INSTANTLY see they are in some way connected. Similar, but still very different outfits. But Alvah has browns and tans in his clothes, his faith is muddled... unstable... dirtied. Now does that show he quickly he abandoned his old faith for Halla or a possible betrayal? Hm. On to his jewelry, unlike everyone else of this death order... that's just a practical design choice, a small hint to the good guys what powers he possesses. He doesn't wear metal. He wears wood like the other lightning user Eclair. Electricity and metal don't mix all that well. Now. Without the other elemental users to show off you won't notice, so I'll just say, he also hasn't maimed himself. In this universe there are only 2 users of the elements at a time. (Ie. 2 lightning users, 2 fire, 2 water, so on). They usually accidently kill themselves in childhood because these powers are horrifically strong but totally unwieldy and notoriously hard to control. The other lightning user we meet, Éclair, has fried one of her limbs useless and shocked the sight outta one of her eyes-- she's got burn scars all down her body, and the other elements aren't fairing much better. Note on Eclair, even disabled and the youngest element user she is, by far, the scariest antagonist of the first act, before Halla becomes God and thus before we meet Alvah. Him being so pristine is terrifying to the other characters. It speaks to how much control he has over his element compared to all of the rest since he basically has the power of Eclair, but can actually properly weld it. Though Eclair kills like... a large handful of people and forced the MC to miscarry and was the one who actually killed the prior god of death, she could be handled since luck always had to be on her side. Many escaped due to the fact she had no control, so pretty boy Alvah here is totally feeding off that energy and making it a smidge more menacing by simply being pretty well doing the same stuff.
And the worst part? I dont tell these stories and no one notices all this thought I put into everyone. u.u But, hey, it's fun hah