Upgrading Wardrobe - Evaluate Current Options + What's Next?

Hi all,

I spent the first five years after undergrad working in a start-up environment (think shorts & t-shirt), but will be interning in a corporate environment this fall and need to upgrade my wardrobe. In addition, I'll be transition from a small city in the SE up to NYC, so I also need to consider dressing for the winter as well.

However, I'm not sure that I'm moving up there until the spring, so I don't want to go crazy on a bunch of cold weather gear quite yet...basically just need the essentials to get me through this winter and look relatively sharp while doing so.

Stats:
Late 20's, 5'9", 175lbs.
33/30 pants. 15 1/2, 33 shirt.

Here are the major items that I own now for my 'work attire':

AE Park Avenues - Black
BB 1818 Fitzgerald Suit - Midnight Navy
BB 1818 Fitzgerald Suit - Charcoal
Express Producer Wool Dress Pants - Grey
3x BB slim-fit dress shirts (see pictures below)
1x each - plain white / blue BB 346 dress shirt

That's the basics right now. The office environment will require a suit on occasion (primarily meeting with clients, maybe 1-2x per week), but will be business casual most of the time (shirt + slacks, no polos or anything).

After reading through a bunch of threads over the past few days, here is what I feel like are the bare necessities I need to add to the wardrobe before heading up there:

Navy Blazer - Anderson Little w/ silver buttons, seems like a no-brainer for someone on a budget?

Dress Slacks (2x) - thinking of going with the BB Madison flat front wool slacks in british tan & light grey - Link. Good color choices? Other slacks options? I tried Banana Republic, but for some reason keep getting the 'pocket wings' - maybe they just don't fit me correctly?

BB Dress Shirts (3x) - I like the BB slim-fit shirts a great deal, but could use input on 'traditional' color schemes and patterns to round out what I already have (see below for pics). Obviously matching my suits + ties is important.

Brown Dress Shoes - My biggest challenge. I will mostly be wearing these with brown khakis / dress pants, and not a full suit. I'm not sure if another pair of AE would be best (seems too dressed up w/o a suit?) or if I should go for a more casual, loafer look. Like these - Link. Or maybe I need both, a dress shoe + a loafer option?

Brown Loafers? - see above

Winter Coat - my last winter coat (black wool) was from high school, so at least 10 years ago...obviously need an upgrade. Was thinking a coat from http://www.sterlingwear.com, either the traditional pea coat (grey) or a single breasted coat like this - Link. Good choice? Thoughts on styles?

Ties - in desperate need of help here (see below), will likely be pushing from The Tie Bar (would rather spend money on nice pants / shirts vs. ties right now, given my situation).

Other needed items, but not necessities for now:

Overcoat - I'm sure I'll need one eventually, but I'm hoping I can get through the first winter just wearing my winter coat over my suit coat if I need to wear both? I know, I know, not ideal but it seems like the good overcoats are $500+ which is probably outside of my budget right now.

Sports Coat - grey or brown? Considering my pant options will likely end up being tan, grey, and charcoal, I was thinking about going with a houndstooth or donegal option in grey like this - Link.

Here is a few pics of my current shirt and tie options:

Ties:








Yes...some of these are very very old.

Shirts






Especially on the tie front, please let me know what I should get rid of and what are the 4-5 basics I should replace them with. Also open to options on additional necessities and future 'nice-to-haves' if I end up moving to NYC and doing this corporate environment thing full-time.

All feedback is much appreciated. Thanks!

I double posted this on accident, but called the moderators on myself to remove the other post. Bumping this one in the hopes of a few replies.

I would recommend skipping the metal button blazer for now. Also, consider a pair of chocolate colored dianite soled chelsea boots for fall/winter. Get a couple of V-neck merino sweaters - navy, wine, light grey (J crew are slim and good price for starting out). Go slow, focus on fit and keep the color palate simple (grey, navy, white, charcoal, etc).