Same about buying: When I see something I like, I buy.
1. If belt then match with shoe.
2. Use 2 to 3 different colors match, preferably: one main/front, one alternate/background and one terriary/accentuation color.
3. Dress to a stereotype. I dress a bit /fancy (e.g. dress shoes and buttoned shirt)
But most days I don’t care, and dress for comfort, lol.
I'm not sure if it's profitable. I think it's a really average idea / business model, to be honest.
As for me, system all the way. 6 t-shirts, 3 jeans, jacket when needed.
I wear the same white alpaca sweater almost every day, the building I work inside is cold. I wear the same pear of jeans almost every day. I pick whatever shirt is clean and feel like wearing.
When I go out to a nice event, celebration, date, etc. I usually wear my Armani blazer and whatever shirt (maybe tie). Takes a few minutes at most.
Hiking/camping - whatever is in my bag that is clean.
It generates combinations with your own clothes, based on the occasion (work, party etc.), weather, season, and a touch of our Italian taste. You can also save the combinations for future use. In this way you can always remember what you have in your closet, discover new great combinations you've never thought of, and save a lot of time.
What I would want would be if I stumbled out of bed, said "where the (expletive) is my warm but super short dress" and Tony Stark's butler made it fly out of under the five cardboard boxes it has somehow fallen behind and went "Dear lady, it is freezing outside. Would you like cheeky printed tights or lace ones with this? Your favorite leather jacket is probably piled up under your Macbook."
Alas, I do not have a robot butler, and so I am seriously considering sticking RFID tags inside my clothing so I can have an app that tells me whether it is, in fact, hung up somewhere and I'm too sleep deprived to see it or I forgot to do laundry again.
She has all the clothes sense that I have never particularly had.
This leaves the purchase decision, which is far more profitable and is (I assume) the focus of your venture. I see 5 primary market segments here:
1. Buy cheap, quick, lower quality. Any generic discount store or retail website fills this niche.
2. Buy cheap, higher quality (or better style), at the cost of time. Mid-tier retailers do well here, but it requires a heavy investment of time and mental energy to know what you want and find it on sale.
3. Buy quality, full price, auto selected. These are your monthly subscription box services.
4. Buy quality, full price, curated. Here you go to a store and someone knowledgeable helps select clothing that fits your requirements. Clothes may be tailored / bespoke. Nothing is ever on sale.
5. Buy quality, full price++, individualized. This is when you have a personal shopper / style consultant who knows you, knows your measurements, and shops at all the stores on your behalf.
If you're solving the question of "What do I buy? What is my personal brand?" then you're playing exclusively in categories 3-4. You want people who are bad at decisions, have disposable income, but also aren't ultra-wealthy and thus don't need the luxury human touch. I'm not convinced that this is an unsolved problem: you'll be competing with incumbents and need to be dramatically {cheaper, better, better marketed}.
Clothing, particularly men's clothing, is pretty darn simple. If there's any real edge left in the "what do I buy" business, it's probably fashion curation based on body type (especially women's body type) which can be quite variable. There are a number of efforts under way here but I don't feel like anyone truly owns this space yet.
And since you asked, my personal datapoints: I am in category #2 (I'm cheap, but I care about quality and am willing to put in the time). Once I feel comfortable enough in my income I'll move directly to category #4 (pay for quality + convenience). I don't feel that category #3 offers good value, and I'm a long way off from affording category #5. I have a curated wardrobe of ~10 very nice dress shirts for daily wear and a set of "black base" jeans / shoes, plus a set of "brown base" jeans / shoes to match with the chosen shirt. Each morning I look at my closet and am done deciding within ~1 minute.
If you think you have an edge here, I'm genuinely curious to know what it is :)