Reddit mentions of Clarks mens Desert Chukka Boot, Brown Suede, 6 US

Quick thoughts:

• Happy to make a whole thing like I did for the other guy, just need a true sense of your budget and what your priorities are if we're going bigger than just shirts.
  
• LA is a particularly strange place for clothes, since most adults dress like kids. I live in San Diego and know the LA world well.
  
• Does your comment about wanting clothes to wear to bars basically mean that you're trying to elevate your style and look better without looking like you're trying too hard? If so, that's a good instinct...at least you're not asking for tips on how to get a fedora for cheap.
  
  I'll see what I can rustle up for $300 for you in terms of shirts and a bit of a style-bump overall. What are your body measurements? Chest, sleeve (like you'd wear in a dress shirt), true waist (not your pants size), inseam, thigh circumference, etc? Use a cloth tape measure, if you have someone to help you take them it's better than doing it yourself.
  
  EDIT: Here's my $300 upgrade for you.
  
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• If you want to elevate your style, first thing I’m going to suggest is to only wear shirts with collars (polos or button-ups) if you’re at work or out with friends/on a date. T-shirts are for sleeping, sports, or running errands, but if you’re going to be anywhere else, wear a shirt with a collar. You’ll instantly look and feel more polished and put together.
  
• Striking the balance between looking good and not looking like these are “special occasion clothes” is about the whole look. You’ll need to snag some better jeans and shoes to look nice and laid back at the same time.
  
• If you shop today, Banana Republic has up to 50% on orders. There’s a trick where you edit the cookie (look in this subreddit, it’s here). I’m assuming the 50%-off prices in this below.
  
  
• Polos
  
  
• Banana Republic Luxe Touch Polo in Navy/Grey/White/Blue Mirage/Brandy wine/Medium blue/Deep rose. Pick 3 at $22.50 (sale price): $67.50
  
  
  
• Shirts
  
• Uniqlo Linen Shirt, navy, $29.90
  
  
• Uniqlo Oxford Shirt, blue and off-white, $29.90 each: $89.70
  
  
• Shoes/Boots: Clark’s Desert Boots, Beeswax, $76.03
  
  
• These are basic and look good with chinos & jeans. They’re classic. They won’t last forever or even all that long, but they’ll get you started and look unobtrusive. They’re as comfy as sneakers but look a lot better.
  
  Here’s a pair of boots, 3 polos, and 3 button-ups for a total of $233. I’m going to recommend that you spend the remaining $67 on getting the Uniqlo shirts tailored to your body. I know you’re planning on losing weight, but this is an urgent style upgrade. The tailoring should cost you around $20 a shirt. Ask around for a good tailor, they’re worth their weight in gold.