Charles Tyrwhitt Dress Shirt, price under $50 on sale mostly $100ish.

Go check Saks Fifth Avenue Slim-Fit Dress Shirt, under $50.

David Donahue Trim Fit Dress Shirt, around $150.

Todd Snyder has nice looking jackets, $400 ~ $1000 - Ashton wears often.

Falconer Jackets -$300 up - Ashton wears often.

Octobre Horace Jacket $200ish - Bradley Cooper wears often.

 

CT shirts are extremely overrated unless you're buying them in bulk with the approx. $35 / shirt cost.

If you're going to spend $100-ish on a dress shirt go with Proper Cloth or Kamakura. 

 
Most Helpful

I recently did a smaller version of this at suit supply - 3 shirts, an overcoat, two blazers. All in all I'm happy with it - if their stuff fits you well off the rack, I think it's worth at least checking it out. 

Shirts I think that you are best off just going custom for them - a proper cloth or Alton lane or whatever should be fine. I've found off the rack shirts to be getting noticeably worse over the last few years - prices up, quality down, and the only saving grace is finding a company that cuts near your proportions. If I'm spending $100+ on shirts might as well have them fit me well. After making the rounds of BB, CT, SS - I think that's my final answer. 

Shoes are Allen Edmonds or similar - get a nice pair and they will last you a lot longer than anything else. Cole haans are fine too - but they are another brand that I've noticed lately don't feel as solid as they used to. Could just be I'm turning into an older curmudgeon - who knows. 

 

I haven't any issues with CT shirts, and at $33 a piece their value is tough to beat in my mind. 

Also worth checking out Bonobos blazers. I've gotten lucky with some good looking sale items, but obviously make sure they fit you before jumping in (no returns on final sale). 

Will be following to hear what others say about shoes. I've been in Cole Haans for the past few years, but unimpressed with the current line up and looking to get something new. Mostly been checking Saks Off Fifth and Nordstrom Rack for good brands that pop up every now and then (Tods, To Boot, Ferragamo, etc.)  

 

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