Just like you i struggle a lot as well lol and this is one of the reasons why i opt in for a hoodie. and tee shirts with graphics. I try to be creative with the hoodies tho. but yes, i feel your pain. it's another reason why i stay away from fantasy. I have dabbled into it in the past but a lot creation goes into it especially if your characters have unique cultural outfits that goes with the world they are in.
anyway, here is a sample of my characters. but yes, hoodies and Tee shirts works
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Do they have jobs / hobbies / culture and wealth / and realistic feasibility?
IE Will dresses in more formal attire thats akin to what men wear in Europe in the turn of the 1900th century and late 1800s, whereas Crow does and can wear stuff like that, he can be caught in some clothes that are similar to the casual fashion of Japan, S. Korean and HK. Will is an indoorsy type, and Crow walks around more.
I actually really enjoy coming up with outfits for my characters
9/10 I'll base it on the characters personality, hobbies or interests; but the first one especially since outside of practical reasons clothing styles are often a form of self expression. Where they're from or family background can play into it as well. Are they into formal attire? goth/alt? do they like bright colors, warm tones, cool hues, etc
I could go on and on about how I chose specific styles for some of my ocs but my method is kinda all over the place~ still there's tons of different approaches and some folks just put their ocs in clothes they like or want (myself included )
my comic has a twisted recursive timeline so i don't want to confuse my readers with different outfits so I try to change outfits daily ( though it's been like 3 days only) but keep them with the same color palette and style. One of my chars wears sporty style, another is a punk and the other is somewhat metal. oh and there's a new military dude haha.
But I also want to keep it as simple as possible for faster drawing and some I also enjoy drawing them without shirts~
here's my character Jace
This is a little genre specific, since my comic is set in a realistic world and the characters doesn't own too many clothes, but I keep track of most of the pieces of the character's wardrobe. As in, I literally have a list in my world-building doc that says he has a black puff jacket, a Matrix t-shirt, a white sweatshirt, etc. So whenever I'm picking the outfit for that scene I can just look at the list of clothing and pick whatever combination feels right. And then for a special occasion I can give him something new.
Also keeping a Pinterest board for each character.
I'll usually give each character a style, and colours which appeal to them, and collect references of different outfits which match that style. When I'm stuck, I'll just trawl through those! My scruffy courier tends to wear clothes which look like they were plucked from the 70's, and he really likes brown shades. (The dork wears an aviator jacket in a spaceship. ) So I have a little library of 70's outfits which I flick through when I don't want him just wearing that default.
I normally decide from the outset what colors and styles they look good in and just randomly pick from there, or I go on google images to find relevant styles.
If you look at the cover page, for instance, they have pretty unified colors in order to fit the mood. But Leila (far left) will always be in something space-themed, because she's a Night Witch, and Gallagher (far left) tends toward business casual (button down shirts, slacks, etc) with a floral or patterned theme because he's Fae. Rory (middle right) is the fashonista, but I have to be careful what colors I pick because his skin tone is BRIGHT. I normally go for custom-tailored stuff given his anatomy, but he looks really good in neutrals/purples/blues/reds, obviously. I try not to do too much red because it'll wash out his silhouette. Khina'i's (middle left) wardrobe is the most basic/least changing out of all of them for character-related reasons. Demetrius (center) is always in blues/blacks/yellows/whites and a more formal edge given his status.
I like to look at specific designers and specific celebrities for inspiration of how my characters would dress--they're people that already made their own look, they kinda do a lot of my work for me. So I have a main character for my comic, Gordy, who wears a jumpsuit with this fancy jacket because he's a free hippie spirit (with a lot of money) who idolizes the boho-hippie style of the Olsen twins (who have a lot of money). So I didn't steal directly, but I took heavy inspiration from two of their looks and made it work for my style in the comic.
I have another character who's hair is based on Zooey Deschenel, she wears a 2010's indie throwback poncho because she's wearing second hand clothes that happened to be available at this school for plot reasons. It's got the 2010's silhouette of skinny jeans on the bottom and way too much knitting on top (complete with knitted fingerless gloves). It's also kind of a joke that she's stuck in this poncho throughout the comic, and honestly it's fun to draw because it is constantly flowing in the wind.
I got another who just dresses in a sweater-vest like it's a magic school because he's the closest I got to a magic school student, so he actually follows the dress code. Easiest person to dress.
But other than personality, I think the biggest thing is asking what your favorite thing is to draw. I love swooshy materials that flow in the wind, I love tailored pieces--those things end up in my character designs a lot.
My characters don't change clothes that often but I try to get into their shoes a bit and think of the style of clothes they want to wear. Then, I look on Pinterest for those kinds of clothes lol. I think it really helps to have some consistent style or motif like @magnavarra does.
My character's clothings are stricly connected to the general aesthetics of the story I am making. For instance, if I chose to do the worldbuilding around Middle Eastern designs, as it is with Menmar, my characters will dress accordingly, which means I'll do tons of research on patterns, moulds, dressing manners for men and women alike (in case there are gender-addressed dressing code, which is the case in such societies) and I'll play around with those concepts.
I'll post some examples here, as I did for the main cast a few months ago in order to promote my story:
Esther and Yami are a married couple in my series, and since they are both quite gender-conforming in their views and dressing code, I think I can illustrate the point I am making when being strictly faithful to Persian designs (I believe I mixed Safavid Era and another one as well, but I'll have to check my research references back again to be sure).
With Nadhine and Raheem I began to allow myself to play with the fashion concepts I studied, giving some sort of androgynous looks in some propositions, whereas I paid tribute to some formal/ regal designs in them as well.
TL;DR: for me, it vastly depends on the main aesthetics of your script/ story setting =)
Consistent colour palette and general silhouette is what I learned to use and love. So usually after I know the world the characters belong to and what their occupation is (student, traveller, warrior), I draw them in one outfit and choose some colours.
After that if I need to change the clothes, I decide what they will or will not wear, if they have a vast wardrobe, if they choose the clothes themselves, what color or item they would never wear, do they like patterns or not, etc.
Look at clothes from Riverdale for example, you always can predict what characters will wear, because they have a color palette and particular clothes and jewelry. So you just have the same things looking slightly different.
You can always have one character that changes clothes more and other who barely do this, because people don't always wear something new, many don't have more than 3-5 items of shoes or bags, most people don't have more than (roughly) 20 items of clothes they wear regularly
I feel you, OP. I chose to give my characters changing outfits to make it clearer when it's a different day from the previous episode, and also so I wouldn't get stuck drawing the same thing forever, but it does slow me down every time I have to pick a new set of outfits. Luckily I like fashion, but then sometimes I get stuck drawing a tricky jacket or something for like 5 episodes, and that sucks.
Each of my characters has their own style, which makes it easier. One of them is a kind of emo dude who basically wears a uniform of a faded black t-shirt and black jeans, though I'll have to give him a jacket as the story/year progresses. For the others, I tend to use google image search for inspiration -- for instance one character is kind of mod, so I just search "mod fashion" and get some ideas from what comes up.