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Westchester - Slip-on Penny Loafer Men's Dress Shoes by Allen Edmonds

What's in a name? Just because a shoe is called a penny loafer doesn't mean it can't look like a million bucks. Case in point, the Westchester, which, like its namesake county that perfectly straddles the space on the map between the city and the country, toes the line between sophisticated yet relaxed, debonair yet down-to-earth. This versatility is a result of combining a sleek 360° welt sole with pin-tuck stitching to create a classic moccasin shape but with an elongated toe that captures a more modern feel. For those looking to truly make a name for themselves, it's also available in Cordovan featuring a Reddenbach single oak leather sole.

Click any link below to view similar styles:

Allen Edmonds Custom Men's Shoes

  • Many of our shoe styles can be ordered in mis-matched and special sizes for a nominal charge through our Consumer Assistance Center at 1-800-235-2348.

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Westchester Penny Loafers

$345.00
Made to Order: 6-8 Weeks
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Westchester Penny Loafers 4.1 5 51 51
Mis-sized . . . . Once trying the 12D in the Westchester, I found my heel slipping in the back of the shoe. The haberdashery I shop at suggested I go with the 11.5E and it should cut down on the slipping and still give me a full fit across the ball of my foot. However, after wearing twice, the half-inch reduction really cramps my toes to the point that by the end of the day after your foot has had a tendency to swell a bit, it becomes really uncomfortable. I have approximately 15 pairs of AEs and they are QUALITY shoes!!! I truly wish I would have settled for the 12Ds or gone to a 12E in the Westchester. May 17, 2013
Sophisticated and Comfortable I love my first AE shoe. I have already bought a second pair. The look and fit is second to none. My only complaint is I have had the shoe for less than 3 months, and the heel is already showing substantial wear. I don't think its the way I am walking... That is a bit disappointing. I hope my next pair will wear better. Should be receiving them soon.. Otherwise, this is a great shoe! April 28, 2013
SIMPLE & SOPHISTICATED LOOKS! This is a beautiful slip on dress shoe. The Westchester reminds me of a colonial times shoe, what Ben Franklin, George Washington or John Paul Jones would have used. Every time that I wear them I get the feeling of been a Colonial Gentlemen! It is just my personal impression! April 20, 2013
Very good dress loafer The Westchester is an excellent dress loafer. Unless you are a seasoned Allen Edmonds customer, I suggest visiting one of their retail locations to ensure getting the right fit. Break-in time is longer with this shoe as the sole and foot bed is initially firmer than with a more casual shoe. March 31, 2013
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(11 Questions : 15 Answers)

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Westchester Penny Loafers
 
2 answers

Is the Westchester fit and toe shape the same as the Grayson?

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Anonymous
4 months, 2 weeks ago
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Answer: 
Yes. They fit the same to me.
3 months, 1 week ago
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Anonymous
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Answer: 
Thank you for your interest in Allen Edmonds.

Yes, the Westchester and Grayson are both manufactured on our 7-Last (97) which is the best fit for the average foot, but also lays flatter in the toe area. By selecting shoes manufactured on the same last that most resembles the contours of one’s feet, customers will achieve a superior fit.

Typically the same size and last can be ordered in all of our shoes. However, each style can fit differently based on individual foot shape. The best way to get a proper fit is to visit a master fitter in one of our retail stores. If this is not possible, keep in mind that products purchased on allenedmonds.com may be returned at any time, as long as the item is unused and accompanied by the packing slip. Trying the shoes on a carpeted surface will help prevent scuffing on the sole and keep the shoe in returnable condition.

Please feel free to contact us with any additional questions.
Allen Edmonds Customer Service
 
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4 months, 1 week ago
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Pairs: Under 5
Favorite:: McAllister
5 months, 2 weeks ago
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Answer: 
The fit is shorter than the Mcallister and about the same as with the Maxfield.
Age: 55-65
Pairs: 6 to 10
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1 month, 3 weeks ago
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Answer: 
Thank you for your interest in Allen Edmonds.

The McAllister is manufactured on our 5-Last (65) which is the longest in length of our lasts, and therefore the best fit for a long, narrow foot. Meanwhile, the Maxfield is a Handsewn style, constructed on our 114 Last which features a slightly shorter vamp with a more rounded toe. Our Westchester style is manufactured on our 7-Last (97) which is the best fit for the average foot. By selecting shoes manufactured on the same last that most resembles the contours of one’s feet, customers will achieve a superior fit.

Typically the same size and last can be ordered in all of our shoes. However, each style can fit differently based on individual foot shape. The best way to get a proper fit is to visit a master fitter in one of our retail stores. If this is not possible, keep in mind that products purchased on allenedmonds.com may be returned at any time, as long as the item is unused and accompanied by the packing slip. Trying the shoes on a carpeted surface will help prevent scuffing on the sole and keep the shoe in returnable condition.

Please feel free to contact us with any additional questions.
Allen Edmonds Customer Service
 
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5 months, 1 week ago
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Westchester Penny Loafers
 
2 answers

Westchester Fit - just delivered today. Feel a bit narrow on my toe.

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Anonymous
Iowa
Same size as my Park Avenue, Charleston, Byron and Hancock styles. Will these stretch enough to get more comfortable? I realize I have not had any time in them yet. Never owned a loafer before.
I also have some slipping, but understand that is normal.

Great looking shoe.
Age: 35-44
Pairs: 6 to 10
5 months, 3 weeks ago
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Anonymous
Iowa
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Answer: 
Mine were initially a bit tight on the toe, but once I broke them in they felt fine.
Age: 18-24
Pairs: Under 5
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3 months, 1 week ago
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pcassidy
Chapel Hill, NC
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Answer: 
Thank you for your interest in Allen Edmonds.

The Byron is manufactured on our 4-Last (234), the Park Avenue on our 5-Last (65), the Byron on our 0-Last (000), and the Westchester and Hancock style are both constructed on our 7-last (97). By selecting shoes manufactured on the same last that most resembles the contours of one’s feet, customers will achieve a superior fit.

Our 4-Last (234) is fairly similar to our 7-Last in that it is the best fit for the average foot, but features a slightly more squared toe; the 5-Last (65) is the longest in length of our lasts and the best fit for a long, narrow foot; our 0-Last (000) features a more pronounced cone and an elongated forepart with a subtly clipped toe creating a sleek silhouette; finally, our 7-Last (97) is the best fit for the average foot, laying flatter in the toe area. Learn more about our lasts by selecting “All About Lasts” under Shoes 101 at the bottom of the page, or by clicking the following link: http://www.allenedmonds.com/aeonlin...

Typically the same size and last can be ordered in all of our shoes. However, each style can fit differently based on individual foot shape. Depending on the age and condition of the shoe, leathers may stretch and wear over long periods of time. If you are unhappy with your purchase, we suggest contacting our customer service center at cacmail@allenedmonds.com or 1-800-235-2348 (Mon-Fri 7:00AM-6PM CST). Because they are brand new, they can either send you a return label or also help better identify what you are experiencing.

Please feel free to contact us with any additional questions.
Allen Edmonds Customer Service
5 months, 3 weeks ago
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Westchester Penny Loafers
 
1 answer

What AE premium polish do I purchase for the brown burnished calf?

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Anonymous
Birmingham, AL
Age: 25-34
Pairs: Under 5
9 months ago
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Birmingham, AL
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Answer: 
Thank you for your interest in Allen Edmonds.

For the Westchester in Brown Burnished Calf, we recommend using our Allen Edmonds Premium Shoe Polish in Dark Brown. We also recommend our Allen Edmonds Conditioner Cleaner.

Use our Conditioner Cleaner to remove any surface area residue and to keep leather soft and pliable. To achieve a fine luster, wipe shoes with a damp cloth and allow them to air dry at room temperature. Follow by applying a coat of our Allen Edmonds Premium Shoe Polish with a cloth or horsehair dauber and allow to air dry. Remove any excess polish by brushing with a horsehair shine brush and buff to a desired shine.

Please feel free to contact us with any additional questions.
Allen Edmonds Customer Service
9 months ago
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Age: 25-34
Pairs: Under 5
Favorite:: The (discontinued) Hale
1 year, 2 months ago
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Dr. Gee
Charlottesville
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Answer: 
Thank you for your interest in Allen Edmonds.

For each of our sole block outs, we use a universal image for each of our 25 styles. This particular image of the McTavish sole features the same sole, the Double Oak Toasted Leather Sole as our Westchester style.

Please feel free to contact us with any additional questions.
Allen Edmonds Customer Service
1 year, 2 months ago
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Age: 25-34
Pairs: Under 5
Favorite:: The Hale is my favorite Allen Edmonds shoe
1 year, 2 months ago
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Dr. Gee
Charlottesville
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Answer: 
Thank you for your interest in Allen Edmonds.

The Westchester is constructed on our 7-Last (97) which is one of our 360 degree Goodyear welted styles.

Please feel free to contact us with any additional questions.
Allen Edmonds Customer Service
1 year, 2 months ago
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Westchester Cordovan Loafers
 
1 answer

Happy Anniversary

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Anonymous
Texas
I was wondering if the anniversary promotion was going to extend to the Cordovan Westchester shoes.
Age: 35-44
Pairs: Under 5
Favorite:: The Melrose
 
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1 year, 1 month ago
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Texas
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Answer: 
Thank you for your interest in Allen Edmonds.

As of now, there are no plans to include the Westchester style into our Anniversary Spring Sale.

Please feel free to contact us with any additional questions.
Allen Edmonds Customer Service
1 year, 1 month ago
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Age: 35-44
Pairs: 6 to 10
1 year, 5 months ago
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Dimby
Chicago
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Answer: 
Thank you for your interest in Allen Edmonds.

The Westchester was created with a dressy fit in mind as it is a member of our Dress Shoe styles as well as the Cordovan Collection. Accompanied by a pair of slacks or a blue suit, they are the perfect foundation on which to build a great outfit.

Ultimately, what each individual chooses to pair their Allen Edmonds with is their own decision; we encourage customers to purchase and wear what they feel most comfortable in.

Please feel free to contact us with any additional questions.
Allen Edmonds Customer Service
1 year, 3 months ago
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Answer: 
Of course you can. These shoes take a shine and are more than appropriate with a suit and tie. Style is just short-hand for what you can get away with. Wear them confidently with your suit and tie. I would.
Age: 25-34
Pairs: 6 to 10
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1 year, 5 months ago
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BestDressedSciTeacher
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Westchester Penny Loafers
 
1 answer

360-degree welt construction?

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Anonymous
Are these shoes 360-degree welt construction or 270-degree?
1 year, 6 months ago
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Answer: 
Thank you for your inquiry.

The Westchester is manufactured with a 360 degree welt.

Feel free to contact us with any further questions.
1 year, 5 months ago
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Melissa
Port Washington, Wisconsin
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Westchester Penny Loafers
 
1 answer

Can you ship these to Australia? and how much roughly would that cost?

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Lindsay
Melbourne, Australia
i live in Melbourne, Australia and i really like these shoes, but your international shipping doesn't show that you ship to Australia. Can you? and if so, how much would that cost?
Age: 18-24
Pairs: Under 5
Favorite:: The Westchester
1 year, 6 months ago
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Lindsay
Melbourne, Australia
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Answer: 
Thank you for your inquiry.

Our website does not offer shipping to Australia. Please contact our Customer Assistance Center at 1-800-235-2348 and they can assist you with an order and answer any questions you may have about shipping to Australia.

Feel free to contact us with any further questions.
1 year, 5 months ago
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Melissa
Port Washington, Wisconsin
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Product Q&A

11 Questions | 15 Answers
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Westchester Penny Loafers
Westchester Penny Loafers has been added to your Shopping Bag.
Extend the life of your shoes with these basic care items:
Full-Toe Cedar Shoe Trees - $24.95/PAIR OR 2 PAIR/$39
SKU SF604
Size:
In Stock
Order Now. Ships in 3-5 Weeks.
$24.95
Premium Shoe Polish by Allen Edmonds
SKU SF549
Color:
In Stock
Order Now. Ships in 3-5 Weeks.
$9.00
Belts should coordinate with the color and style of shoes being worn. For these shoes we recommend:
Wide Basic Dress Belt
SKU SF39501
$98.00