Depending on the item I'll usually go with a brand I trust for that item or which specializes in it. It can take some time to find the ones that fit your style, whose sizes match your proportions, and fit in your price range, but it's worth it. You don't need to buy from a different brand every time; just find a few whose target demographic is very similar to you. Department stores like Nordstrom are great for trying out a ton of different brands.
For me personally, I get all my jeans from Page, all my chinos from Bonobos, all my boots from Thursday, etc. Koio also has some solid sneakers. I like Uniqlo for essentials in general but the Slim Fit T-shirts from H&M have been incredible for me--for the cheap price they're super comfy and surprisingly good looking on me. Lululemon in XS tends to fit me spot on too so I get a piece from them every now and again, but the Durable Shirts from Ten Thousand are my go-to for the gym. For leather jackets I have a couple from Allsaints and a beautiful biker jacket from Boda Skins. I also have an amazing wool overcoat from Reiss plus a couple of my go-to overshirts. Years ago I got a ton of stuff from Guess based on a recommendation from one of Chase' articles...I still have one of their wool peacoats in my closet.
If you have a hard time finding stuff that fits you exactly, you can go MTM too. Places like Proper Cloth can get you a great fitting dress shirt. Personally I've found the algorithm at Ratio Clothing to suit me better for button ups. I also have a couple nice tees from Son of a Tailor but I have a hard time justifying the cost over the off-the-rack H&M shirts. Suit Supply also does custom blazers, shirts, pants, etc. in addition to suits, and you can really go crazy on getting exactly what you want.
For accessories, I've had good luck with local artist events and Etsy. You'll find a ton of a unique items--some literally one of a kind! But I exclusively get gloves from Dents--good enough for James Bond, good enough for me.
I don't think he's active anymore, but for finding inspiration and a style (specifically for game), I thought Darius' content was really valuable. His website seems to be down but his old Pinterest board has a lot of great looks for different styles:
https://www.pinterest.com/sexystyleforjoe/_saved/
Lastly, the secret sauce is finding a good local tailor. Most of the time clothes won't fit you perfectly, but find an item that fits you in the key areas and a tailor can work his magic to get you a perfect fit. At this point, I think 50% of my wardrobe has seen my tailor at one point or another.
reasonclothing.com
. Personally I love bland and simple fashion. I never used to care about it, but now I can put a few well fitting jeans/chinos with a decent shirt / t-shirt and be "better dressed" than most others. The standards for men's fashion are so low that it really doesn't take much to dress decent
