The 5 Starter Pairs for the Modern Gentleman

The modern gentleman should have more than one pair of shoes. Shoes, while meant to be used, should be taken care of as well. Thus we should have more than the one beater pair that is the usual practice. It is fine for the disposable cheap synthetics but not good for leather pairs.

Leather shoes should be cycled throughout the week, work shoes especially. It is best practice to have at least a couple of pairs that are exclusively for work. Normally a derby and an oxford or dress loafer are good choices for work shoes. So here are the five basic pairs every modern gentleman should have:

1. The Casual Beater

This pair is your casual go-to pair. You wear this pair and when the time comes for it to retire, you’ll still keep it because you feel so at home with them. Us men love our beaters and would try to find an excuse to wear them as much as we can. Usually sneakers, espadrilles and rubber shoes fit the bill for weekend shoes. For the purposes of this article, we shall refer to beaters as our casual-weekend go-to pairs.


This year, sneakers and rubber shoes are slated to make a comeback after driving loafers took center stage last year.

2. The Derby

Derby refers to an open type lacing system and hence is easier to put on. This makes the derby a less formal pair compared to an oxford. The derby usually comes in either plain toe or wingtip if you want a bit of versatility to the pair. Generally it is easier to dress down a derby especially if you have a wingtip design. Once you go and use a derby cap toe, however, it is quickly elevated to a dress shoe which limits the ability to dress it down.

Derby shoes make for good work shoes. They are generally easy to wear with their open lacing. The ability to dress them down makes them versatile in the workplace and easier to pair up with chinos or jeans. It is also easy to pair them up with a suit so as long as the fit is proper and your pair is made on properly proportioned shoe last. This would be the basic of basics for a modern gents shoe wardrobe.  I could say that this is to become your leather pair which can easily be considered as you beater pair especially for work.

3. Standard/Dress Loafers

Loafers are the most relaxed of all the shoe types that are available. Any pair without any lacing and would only require the wearer to just “slip-on” a pair is generally considered a loafer. Loafers are generally considered as a dress down shoe thus is perfect for Fridays at the office. Although there are some exceptions where loafers are worn with suits to formal events, it is not advisable to wear standard loafers to black tie events. There are, however, dress loafers which go well with suits and are designed to work well with very formal occasions especially if you are a it on the fashion forward spectrum.

So in general, standard loafers are good for relaxed and dress down occasions while properly designed dress loafers can be used for black tie events. Also, driving loafers are casual loafers and are best worn with chinos, jeans or shorts with a sports shirt. Driving loafers should not take the place of your standard loafers especially for dressier events or even for casual Friday at the office. Personally, I categorize driving loafers under the casual beater pair category.

4. Formal Oxfords

Oxfords are on top of the dress shoes hierarchy. The closed lace system is considered to be the most formal thus making the Oxford the go-to shoe for dressy and classy events. The simpler the design, the more formal it becomes. That is the general rule that I follow with designing Oxfords. Full brogues (wingtips) can be dressed down depending on their color but is still too dressy for a chino-sport shirt combo. The most dressed down one could do would most probably be a chino-button down shirt combination. Wearing an Oxford to work symbolizes professionalism and a strong sense of responsibility. From the boardroom to the ballroom, the Oxford is a definite must have for every modern gentleman. How formal you want it to be would depend entirely up to how comfortable you are with your “power shoe”.

Oxfords come in a myriad of styling, very much like the derby. I consider wingtips as the most dressed down of all Oxford toe cap styles. This is because wingtips tend to be very busy, especially with brogues. It tends to become a showy pair, complete with all the bells and whistles. While not necessarily a bad thing, I personally like to keep my Oxfords simple and sleek.

Contemporary plain toes, depending on the design on the toe area, can make as a very nice statement pair which can show a fun and quirky side to an otherwise plain and stiff pair.

Oxford cap toes are my personal favorite for regular office and dressy occasions. It shows that you take your work seriously and that you respect the occasion. It is generally a versatile formal pair able to be paired with a standard suit, tuxedo and Barong Tagalog.

Wholecuts are placed above the rest in terms of dressiness. They are the testament of the shoemaker’s dedication to his work. Made from one piece of leather and connect at the back, it is the sleekest of all designs with some room for brogues, a medallion and stitch designs to liven things up. But make no mistake, the wholecut stands on top of all pairs in terms for formality, even with some design tweaks.

5. Monk Straps

The monk strap is a pair which I find to be very versatile, especially ones that come in different shades of brown. A monk strap can be worn for smart casual to casual occasions when dressing it down. It will look good with jeans or chinos (especially the double monks) while being completely relaxed. If you need to dress up a bit it can also be worn with suits for formal and business events. As long as the color coordination rules are met, you cant go wrong with the monk strap.



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