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Purchase advice - Penny Loafers in NYC

Shoefish8

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Hi SF,

TLDR: What penny loafers should I get a relative to buy for me in NYC this weekend on a budget of $2-300

I am an aspiring(!) shoe aficionado that for some odd reason has found himself without a single pair of shoes suited for leisurely summer days. I've spent the last week scouring forums acquiring and honing in on my preferences. I am from Sweden where the supply of good quality shoes is not only scarce but quite expensive, where international (Non-EU) purchases pretty much adds on 30% plus shipping to the price. Luckily, my father is going to be in New York over the weekend, and is willing to pick up a pair for me.

Disclaimer: I am not knowledgable so please assume the worst!

Goal: Purchase a pair of shoes in NYC this weekend suitable for the summer in New York. This can include ordering domestically to his hotel assuming they arrive before he leaves (which I think is on Tuesday).

Use: All around shoe that I can use in the office (my own start-up, so no rules), or pretty much any leisurely setting I might find myself in. This is kind of where the heart of the debate lies, as I'm trying to reason between finding a shoe that fits all occasions.

About me: 22 year old college student that likes classical shoes and a somewhat preppy style of clothing. Today I own a pair of tan oxford brogues and black derby's, along with other shoes not suitable for summer.

Budget: $400 MAX. This can include getting two pairs, one more formal / one casual, to maximize my utility. I'd rather not go above $250 for one pair, out of fear that my dad will think I'm insane. Optimally I would like to get one pair in the $2-300 range that suits my needs.

Preferences: Quality is important, both in the sense of knowing they will last and because a pair I know is good quality will bring me more enjoyment. I know welted doesn't say much about the overall construction but I'd like to at least rule out cemented uppers.

Regarding style I'd like to say my personal preference is at the top of the formal spectrum but my rationale says I might need to slide down the scale to accommodate for my age / style / intended use along with versatility. I'll try to explain what I mean with some links below.

As the title reads I've pretty much decided on penny loafers. If I were to go with two pairs, say one more formal pair of penny's, I might be persuaded to hitch a pair of boat shoes as a casual alternative. I will not be entertaining tassle loafers or monks etc.. Regarding strap style, beefrolls or full length really depends on the overall aesthetic of the shoe.
Regardless, I really want a leather sole and preferably a stacked heel in a lighter color. I also have a thing for whiskey tans.

Links to shoes I like:
http://www.dsw.com/shoe/cole+haan+hudson+penny+loafer?prodId=310584&category=dsw12cat1970004&activeCats=cat20192,dsw12cat1970004 Cole Haan Hudson Tan: First penny loafer I saw, which got me going. I really like the overall style of the shoe. It seems like it fits my needs perfectly, not too casual bot not too dressed up. However I got to reading and realized these were not of quality, which has me seeking for alternatives.

http://www.rancourtandcompany.com/men-s/penny-loafers/weltline-penny-loafer-calfskin.html Beautiful shoe which breathes quality. Everything I've read about Rancourt is great. I'm worried as I mention below that I might be restricting my use with these. Plus are they available for retail?

http://www.ralphlauren.com/product/index.jsp?productId=4325814 Love it! Beautiful stuff. The drawback is price and versatility, this is what I mean by maybe restricting myself by purchasing at the higher end of the spectrum. Can these be rocked in a pair of shorts by the beach? Maybe not...

http://www.ralphlauren.com/product/index.jsp?productId=18660566 Good blend between classy and casual, with the thicker seam and wider front. Dislike the color somewhat.

http://www.ralphlauren.com/product/index.jsp?productId=12652085

http://www.brooksbrothers.com/Leather-Boat-Shoes/608H,default,pd.html?dwvar_608H_Color=DKBR&contentpos=29&cgid=0522 Pair of nice boat shoes

http://www.rancourtandcompany.com/men-s/penny-loafers/beefroll-penny-loafers.html Great pair of shoes, but in this case I'm worried I might feel they are a bit low on the spectrum. Same goes for the absolutely stunning Oakstreet Bootmakers below:

http://oakstreetbootmakers.com/footwear/beefroll-penny-loafer God damn am I in love with this shoe. The contrast stacking is awesome. Precisely what I like. I am worried that it is a bit too un-formal and that I won't be satisfied. I have also read that the construction is not as great as it first seemed, and that some models didn't seem to be stitched but glued?

http://www.shop.carminashoemaker.com/articulo.asp?idarticulo=5342860 Obviously.

http://www.aldenshoe.com/DrawProducts.aspx?Action=GetDetails&CategoryID=10&ProductID=17&PageID=9

http://www.quoddy.com/true-penny-loafer/ Great shoe in whiskey, a bit rugged maybe. Are these available for retail or are all ordered?
Well I could go on and show you more shoes I like, but I realize I've already rambled on for WAY too long. I suck at writing concise posts. I hope someone can empathize with me and knock some sense into my scattered mind.
Thank you in advance SF, I really appreciate and need it!
 

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