I've never been into boots. Recommend me a boot that can get me around in a Chicago winter that I can still hang out at a bar in.
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Cole Haan shoes
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Redwing Iron Rangers or Redwing Blacksmith (I prefer the look of the cap toe on the Iron Ranger)
Wolverine 1000 Mile Boots.

If you want something heavier looking that's not as "dressy."
Merrell Wilderness.

I will say, though, that the Redwing Heritage soles kind of suck for ice. I replaced mine with Vibram for like 30 bucks at my local cobbler.
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Lol, Matt R. from Zappos kind of nails my thoughts on those Red Wings. Good looking boot though.

These boots should come with a timber claim and an axe. Sadly, I have no business owning a pair of these boots. As soon as I unboxed them, I realized that my life was a wasted opportunity, and I lacked the construction background, or ranch, or metal shop, or other manly profession to be worthy of these workhorses. These boots are for every guy in every truck commercial. But they are comfortable, stylish, and tough as nails. If you can pull it off, these are some amazing pieces of craftsmanship.

I might be able to pull off those Merrell's.
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Best slacks and button downs for a reasonable price?

Slacks should have good fitment. Don't like the baggy disheveled look. Open to all colors.

Shirts preferably slim fit. Again, I like my clothes to fit.

I'm about 5'11" 185lbs, if anyone about that size had any insight.

Also, almost forgot. Shoes. Super important. I've never had a comfortable pair of dress shoes. Would preferably start with a versatile pair that works well with a lot of pants and styles.

Thanks.
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Give me a price range. 'Reasonable' can mean a wide range of things.
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Go to Macy's. Lots of slim fit options there.
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Get yourself a tailor. Add $20 to the price of any pants and they will fit exactly how you want them to.
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Can't go wrong there. I've got 3-4 pairs of them including the ones I'm wearing now. They're comfortable and are really nice quality, but they can be a little pricey. I've got a shit-ton of shoes, so I can't drop $225 every pair, but when I find a pair I really like, they're worth it.
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Yeah. You can either pay to buy bespoke, or you can find one line/style/fit that you know fits just right and buy in bulk.
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DSW stores always have a ton of Cole Haan for like $100-$160. You can get some dress shoe finds there for sure.
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Have an opportunity for an office job I think I'll get. Initially, I need to get a decent wardrobe together, but don't want to break the back to do it as I've been of work post ACL surgery.

If say shirt pant together under $100.
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Silly question but I'm wondering at what weight you can start pulling off the slim fit look
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I would say when your waist is noticeably more narrow than your chest.
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When you are slim. No gut.
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