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One loafer above all others

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@DcDrape -- Depending on your age, what you wear with them, the location you'll be wearing them [geographically] will largely determine which type of loafer and what features would be best for your first pair. As someone earlier eluded, certain geographic locations could make something like a horsebit or tassel loafer seem overly dressed, and unless you are someone comfortable trend setting, then you'll probably be better served with a pair you'll wear often like a penny or subdued Belgian. I'd opt for City rubber sole over leather if this is just one pair you have that you might wear frequently.
It's funny because in my city the only people I see wearing tassel loafers tend to be older and more conservative.
 

apd90700

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It's funny because in my city the only people I see wearing tassel loafers tend to be older and more conservative.
That would be the same here, and if OP is going for his first pair of loafers, he would want to be age appropriate for his geographic region. Usually a penny loafer blends a bit better than something like a tassel or horsebit which has the extra visual interest, and while actually less formal [more on the shoe usually being less formal] they come across to the unaware as overly formal or ostentatious.
 

dieworkwear

Mahatma Jawndi
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That would be the same here, and if OP is going for his first pair of loafers, he would want to be age appropriate for his geographic region. Usually a penny loafer blends a bit better than something like a tassel or horsebit which has the extra visual interest, and while actually less formal [more on the shoe usually being less formal] they come across to the unaware as overly formal or ostentatious.
I personally like the contrast between the wearer and his clothes.

I think guys who are in their 30s and 40s can look great in tassels because it's somewhat unexpected, so long as the rest of the outfit isn't too #menswear. But in a classic, tailored outfit, there's something charming about a younger guy in an older man's shoe.

I feel the same way about feminine things. Belgian loafers can look really good on very masculine guys cause it softens their edge. There's a bit of play between the daintiness of their shoe and the ruggedness of their build/ appearance.
 

Duke Santos

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It's funny because in my city the only people I see wearing tassel loafers tend to be older and more conservative.
Being a Chicagoan, I feel the same way. Older, North Shore guys who spend their weekends at "the club." Penny loafers--despite their undeniable prep/ivy connotation--just seem both more urban and urbane. That's just my opinion though.
 

Naive Jr.

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Being a Chicagoan, I feel the same way. Older, North Shore guys who spend their weekends at "the club." Penny loafers--despite their undeniable prep/ivy connotation--just seem both more urban and urbane. That's just my opinion though.
That's very wierd to read Duke Santos here who calls himself a Chicagoan and talk about North Shore guys and the club but somebody born and raised across the street from Lincoln Park, then Rogers Park and Evanston, then Lake Forest doesn't recognize North Shore North Side Chicago Lake Michigan in Duke's sociological decrees. With all due respect, Duke's soul swings like carpetbagger University of "Chicago". North Shore North Side Lake Michigan feels all these styles of loafers have each their own iconic beauty to be worn by anybody anytime. Duke may be riding high somewhere on Sheridan Road some of the time but his soul is behind those gates in Hyde Park on the other Side of town, no offense intended.
 

dieworkwear

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That's very wierd to read Duke Santos here who calls himself a Chicagoan and talk about North Shore guys and the club but somebody born and raised across the street from Lincoln Park, then Rogers Park and Evanston, then Lake Forest doesn't recognize North Shore North Side Chicago Lake Michigan in Duke's sociological decrees. With all due respect, Duke's soul swings like carpetbagger University of "Chicago". North Shore North Side Lake Michigan feels all these styles of loafers have each their own iconic beauty to be worn by anybody anytime. Duke may be riding high somewhere on Sheridan Road some of the time but his soul is behind those gates in Hyde Park on the other Side of town, no offense intended.
I think it's pretty common for tassel loafers to be associated with an older, conservative crowd. Not sure that's controversial. The famous story about George Bush confirms as much.
 

Jmr928

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“North shore north side”? They’re worlds apart. I’m not sure I understand the context within which the two are strung together like that.
You forgot Chicago Lake Michigan. I dunno about you but personally North Shore North Side Chicago Lake Michigan is my favorite neighborhood.
 

Phileas Fogg

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You forgot Chicago Lake Michigan. I dunno about you but personally North Shore North Side Chicago Lake Michigan is my favorite neighborhood.
all the bases are covered, that’s for sure.
It’s the new “neighborhood” being pitched by developers. Sort of how Lincoln Park continues to expand and how “West Town” was all of a sudden discovered.
 

Duke Santos

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That's very wierd to read Duke Santos here who calls himself a Chicagoan and talk about North Shore guys and the club but somebody born and raised across the street from Lincoln Park, then Rogers Park and Evanston, then Lake Forest doesn't recognize North Shore North Side Chicago Lake Michigan in Duke's sociological decrees. With all due respect, Duke's soul swings like carpetbagger University of "Chicago". North Shore North Side Lake Michigan feels all these styles of loafers have each their own iconic beauty to be worn by anybody anytime. Duke may be riding high somewhere on Sheridan Road some of the time but his soul is behind those gates in Hyde Park on the other Side of town, no offense intended.
I can't take any offense because I literally have no fucking idea what the hell you were grasping at.
 

Jmr928

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all the bases are covered, that’s for sure.
It’s the new “neighborhood” being pitched by developers. Sort of how Lincoln Park continues to expand and how “West Town” was all of a sudden discovered.
“Do you think we can charge more for this space if we include Lincoln in the name and use up some good will from Lincoln Park? What about something like Lincoln Yards?”
 
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I personally like the contrast between the wearer and his clothes.

I think guys who are in their 30s and 40s can look great in tassels because it's somewhat unexpected, so long as the rest of the outfit isn't too #menswear. But in a classic, tailored outfit, there's something charming about a younger guy in an older man's shoe.

I feel the same way about feminine things. Belgian loafers can look really good on very masculine guys cause it softens their edge. There's a bit of play between the daintiness of their shoe and the ruggedness of their build/ appearance.
Agreed on the tassels and tailoring in general. I'm in my early 30s and traditional menswear is something of a lost art (or style?).

I live in DC which is the land of dark grey and navy suits with white or blue shirts, but DC isn't exactly a stylish city. I have an older coworker who is impeccably dressed 24/7, and he's the only one to comment on the finer details of my outfit be it shoes, tie choice, or the fabric of my jacket.
 
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Being a Chicagoan, I feel the same way. Older, North Shore guys who spend their weekends at "the club." Penny loafers--despite their undeniable prep/ivy connotation--just seem both more urban and urbane. That's just my opinion though.
This article from the NYTimes always comes to mind when talking about the conservative nature of tassel loafers.
 

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