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Discussion Starter · #1 ·
Gents, Iam looking for a little guidance on the topic of penny loafers. Full disclosure, I have never been a “loafer man”. I have never had much trust in a shoe that doesn’t get attached securely with some kind of laces. With that being said, I want to dip my toes in to the waters, so to speak. I have been looking for some affordable loafers on ebay. I have recently found a NOS pair of unlined Dexter in brown pebble grain, and a pair of Churches in smooth burgundy. I am leaning towards the pebble grain, but the Church name makes me think they might be a better pair.

All things being about equal are there arguments against pebble grain? Will more seasoned loader wearesr point and laugh at me. Maybe I am over thinking this whole thing?
 

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For a first pair of loafers, I'd personally go with the standard burgundy as it's much more versatile.
It can be tough to get a good fit with loafers though, so if it's only between those 2, go with the pair that fits you the best.
 

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It would depend on how you plan to wear the loafers. Pebble-grained Dexters are going to be pretty casual and will probably look best with chinos, jeans, etc. The burgundy Churches are probably on a sleeker last and will be more versatile and can be worn with chinos, jeans, and dressier wool slacks. I have a pair of burgundy Santoni loafers that dress up pretty easily - I don't think you can do that with the pebble-grained Dexters.
 

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Getting the fit right with loafers (or any shoe, really) is extremely important and they usually feel different than lace-ups. Don't get discouraged and give up if the first pair you get isn't right. I'm at the point now where I dislike the feel of lace-ups and will never buy another paid.
 

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In my opinion I dont see anything wrong with pebble grain so long as it fits in with the overall look of the loafer - which would be rougher, more casual finishes/details.
 

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I was going to say "Ask Doctor Damage" but he was alert.

I have more loafers than anyone should. Every time I think I have it right, another loafer appears and I have to try it. It's a sickness, especially when I live in an area where loafers are completely impractical seven months of the year.
 

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In my opinion, it depends on how old the Dexters are. Dexter is one of those brands that the more recent the make, the worse the quality. Some of the older made in USA Dexters are great shoes and well worth a slight premium.
 

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In my opinion, it depends on how old the Dexters are. Dexter is one of those brands that the more recent the make, the worse the quality. Some of the older made in USA Dexters are great shoes and well worth a slight premium.
You're quite right about Dexter. It's probably not smart for the o.p. to try vintage shoes for his first time since he doesn't know the sizing and fit of the various (vintage) brands. If I were him, I'd go to an AE store and try a few different styles, and buy the most comfy feeling pair.
 
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I have more loafers than anyone should. Every time I think I have it right, another loafer appears and I have to try it. It's a sickness, especially when I live in an area where loafers are completely impractical seven months of the year.
I live in the same sort of weather situation too. These days I just say "f*** it" and wear the loafers if the snow isn't too deep. I figure I don't know how long I'm going to last, so there's no reason to have a stockpile of shoes that were never worn. That being said, I don't go out of my way to abuse my shoes.
 
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^ I get it.

You know what my favorite pair of loafers is? A really beat-up pair of Allen Edmonds Lawrence (strap penny) with a lug sole. The heel counter has collapsed and I can wiggle into them like boat shoes. They look like hell and I love it.

I bought them at the thrift shop for $5 about 10 years ago.
 

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Discussion Starter · #12 ·
Thanks for the input gents. I am going to stick with it and try to find a pair that fit really well. I like the look of them in pebble grain, so that is where I will spent my time looking. Since the pebble grain is more casual, I will look for an unlined version that can get lots of casual warm weather wear.

Fit has always been an issue, and I think I will have to try on a lot of shoes to find the best fit for me.

I think the casual look of the pebble grain without socks would look good with shorts.
 

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I personally would be cautious of buying loafers online unless you are familiar with the particular last that it is on. I've have been burned a few times when it just wouldn't fit right, you don't get the luxury of being able to adjust the fit like you can with lace ups.
 

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Discussion Starter · #14 ·
I personally would be cautious of buying loafers online unless you are familiar with the particular last that it is on. I've have been burned a few times when it just wouldn't fit right, you don't get the luxury of being able to adjust the fit like you can with lace ups.
I think that is one of the reasons I have not made much of an effort to get into a pair. I am going to try on some locally before I start throwing money around online.
 
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