Fashion Outlets of Chicago near ohare has a lot of outlet stores and discounts. Recently bought 3 new pairs of jeans from Levi’s for $100, bought more at Gap also cheap. This is a solid option if you need a lot of basics for your wardrobe. They do have higher end places on the second floor. I bought a really cool shirt from a designer called Sandro. More on reddit.com

Nordstrom Rack, the one on 23rd is better than union square.

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My go tos: Core/basics - Banana Republic, J Crew, Buck Mason, Todd Snyder, Bonobos, Faherty, Flint and Tinder, Charles Tyrwhitt, Aran Athleisure - Lulu, Vuori, BYLT, Western Rise, American Giant Outdoor - Arc’teryx, Patagonia, Outdoor Research Shoes - Reiss, Cole Haan, Sorel, Nike, Adidas, Birkenstock Underwear - Ex Officio, Saxx More on reddit.com

With all due respect, you just described the most basic men's wardrobe lol. You can close your eyes and point to any number of brands and they'll have what you're looking for. What's your budget? What's your office attire like? Do you prefer things to fit more fitted, or a bit looser? For cheap, I'd start with Uniqlo, or Banana Republic Factory or Gap Factory, The Tie Bar, Old Navy, etc.,. Slightly more expensive, you've got JCrew, Madewell, Banana main line, Gap main line, Bonobos, Club Monaco, Nordstrom Rack. Even more expensive, you've got SuitSupply (they sell everything from t shirts to tuxedos), Sandro, Nordstrom main line, Billy Reid, Scotch and Soda (if it's still around). My advice is to buy the best quality you can afford. Buying better quality items means a longer lasting garment. Also, think of your wardrobe as a capsule. Buy pieces that go with multiple different things. Sweaters that can be worn with jeans and with chinos, jackets that can go with multple styles. Buy the leather Vans so they are easier to clean, and you won't be tossing them in the garbage after two years. Or swap out the Vans for more streamlined casual leather shoe altogether. SuitSupply makes a decent dress leather sneaker, Madwell does too. I think Madewell's shoes are like $90 or so? SuitSupply is definitely pricier, but the leather quality is better. Avoid places like H&M and Zara for your staple pieces. The quality is craptastic, and you'd be contributing even more towards global waste. Not saying other brands mentioned are any better, but these two brands are prime offenders when it comes to fast fashion and global waste. Same goes for Shein. Avoid them. Also, all of the places I mentioned have brick and mortar stores, or are available in brick and mortar stores, in the city. More on reddit.com