To wear a penny loafer with a sock you should wear mid calf or crew length socks which match the color of your pants or trousers which gives you a classic look.
You can also wear the penny loafers with no show or linger socks which can keep you an appearance of not wearing socks while also avoiding bare feet.
You can wear classic penny loafers by pairing the penny loafers with some chinos, shorts, jeans, and even a polo shirt or casual short for a casual look.
If you want a more formal look when wearing the classic penny loafers you should pair the classic penny loafers up with a blazer, suit or tailored trousers and a dress shirt.
For a smart casual look you can pair the classic penny loafers up with dark denim jeans, a white t shirt and a blazer.
Chinos in colors such as cream, blue, or khaki are also great for wearing with classic penny loafers, especially for summer evening wear.
Penny loafers also can be worn with shorts, and most particularly in warmer months which can create a relaxed yet stylish outfit.
While classic penny loafers can also be worn with a suit, it's often preferred to wear the classic penny loafers with a blazer to get a more relaxed and polished look.
And tailored trousers, like wool trousers also pair well with classic penny loafers and provide you with a more formal look, especially when the penny loafers are paired with a collared shirt and sweater or jacket.
Penny loafers can also be worn without or without socks, although the penny loafers are more comfortable when wearing socks.
If wearing socks with classic penny loafers or penny loafers in general, you should consider wearing thin, dark colored socks which helps to maintain a streamlined and good look.
No show socks are also good for penny loafers if you want to wear the socks with the penny loafers without the socks showing.
For penny loafers it's recommended that you size down, especially if you're between sizes, or if you plan on wearing the penny loafers without socks.
If you plan to wear the penny loafers with socks then you may want to size up to allow more room for the socks.
For leather penny loafers, a snug fit when trying them on new is ideal as the leather penny loafers will naturally stretch out and mold to your foot shape as you continue to wear them.
Penny loafers should not be too tight even when first worn although the penny loafers should fit snugly but not be restricting.
When the penny loafers are properly fitting they should be snug but allow for a little room for your toes to breathe and move around and the heel of the penny loafer should also fit snugly without slipping and you should also be able to wiggle your toes comfortably within the penny loafers.
If you can't wiggle your toes comfortable in the penny loafers or they are causing pain then they are too tight and you should go up a size.
Basically the penny loafers should feel close to your feet, but they should not be too tight or so tight that the penny loafers restrict any circulation or cause discomfort.
Leather penny loafers also naturally stretch over time, so a snug fit initially, allows the leather penny loafers to mold to your foot shape as you wear them.
It is OK to wear penny loafers with a suit as a suit and penny loafers are considered stylish, especially when being worn for a more relaxed formal look or casual look.
Penny loafers also offer you with a good balance of comfort and formality which makes the penny loafers and suits a versatile option for several occasions.
Penny loafers can be worn with any type of jeans, chinos or even dress pants and even shorts can be worn with penny loafers.
For pants, black or white pants are often best for wearing with penny loafers although blue jeans can also be worn with penny loafers if you're not worried really about style.
To make your penny loafers look good, consider the fit and style and consider the clothing you're wearing with them as well.
Penny Loafers are very versatile and can be dressed either up or dressed down and you can also pair penny loafers with tailored clothing pieces like trousers, coats, blazers etc for a good polished look.
If you want a casual and style look with your penny loafers you can pair the penny loafers with some chinos, shorts or even jeans.
Ensure the penny loafers are clean and that they also fit good and also consider socks which makes them look even better.
Wearing penny loafers with jeans is a classic and also stylish combination which can be dressed down or dressed up as you see fit.
The key with wearing penny loafers with jeans is to choose the right fitting jeans and right color and to also consider the overall style of your outfit.
But if you're not into style and just want to wear penny loafers with some jeans you can wear them with any jeans that you prefer to wear them with.
You should wear socks with penny loafers as wearing socks with penny loafers makes the penny loafers more comfortable to wear and is also more stylish as well.
If you don't want the socks to be seen easily you can wear ankle socks and long enough pants that cover the shoe top.
Penny loafers have a classic design and a timeless style which has not gone out of style which makes the penny loafers a still very popular and versatile shoe option for various outfits.
The reason why you put pennies in loafers are because the loafers have a place where a penny could easily be kept in case you needed to use it for something such as a payphone call back when payphones were cheaper to use.
Way in the beginning payphones used to cost a penny but by the 1930s the payphones started costing a nickel and then a dime and then the cost to continue to increase.
Later on putting a penny or other coin in a penny loafer became a fashion statement.
The slit in the strap of the penny loafer was designed to hold a penny which is why they are called penny loafers.
A penny loafer is a type of casual leather shoe that has a decorative and slotted leather strip over the upper part of the shoe that a coin such as a penny can be placed.
Penny loafers are a type of slip on leather shoe that is worn in casual situations although you can wear penny loafers any time you want to wear them.
Back in the 1930s, the design of loafer shoes allowed just enough space for a penny in each shoe, which was actually a great hiding spot for a little pay phone change in the age before mobile phones and when a payphone call didn't cost that much.
Then later on in years down the road, when payphones cost more than what you could keep in your shoe, silver coinage was then still added to penny loafers as a statement.
Loafers are low rise and they feature a slim profile heel and leather upper, and you should wear loafers without socks or ideally with ankle socks that are invisible.
There are also penny loafers that have a trademark "saddle" across the vamp, tassel loafers as well as horsebit loafers and kiltie loafers.
Penny loafers are worn by both men and women and are a versatile shoe that can be worn for various occasions which include casual outings and formal events.
Penny loafers are more popular with people that are seeking a comfortable and stylish slip on shoe.
Famous people and Icons that wore penny loafers include John F. Kennedy, Elvis Presley, Miles Davis and even James Dean.
Penny loafers for men are a staple in menswear and are often paired and worn with suits for a more formal look or with casual outfits such as a polo shirt and jeans for a more relaxed vibe.
Women wear penny loafers with skirts, dresses or even jeans for a chick and effortless look.
And historically, Ivy League students, wore the Penny Loafers especially during the mid 20th century and they were known for wearing penny loafers as a preppy and fashionable choice.
And because penny loafers are easy to put on and are easily slipped on, they can make a good stylish look for people seeking a polished appearance and comfort.