There are only two decision points in daily clothing: (1) What to buy, and (2) what to wear. If you've bought correctly, the "what to wear" decision is 5-120 seconds and no more. There's no pain to alleviate here... even a free service that told me what to wear today would be useless to me, and would take longer than just choosing myself.<p>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:<p>1. Buy cheap, quick, lower quality. Any generic discount store or retail website fills this niche.<p>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.<p>3. Buy quality, full price, auto selected. These are your monthly subscription box services.<p>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.<p>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.<p>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 <i>need</i> the luxury human touch. I'm not convinced that this is an unsolved problem: you'll be competing with incumbents and need to be <i>dramatically</i> {cheaper, better, better marketed}.<p>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.<p>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.<p>If you think you have an edge here, I'm genuinely curious to know what it is :)