Most guys tend to rotate between three different types of footwear depending on occasion and/or season: ugly, square toed dress shoes, dirty sneakers, and flip flops.
You can easily do better.
The following are my 4 picks that will help you level up your shoe game in a major way.
When it comes to dress shoes most guys tend to play it safe by going with a pair of oxfords.
Although oxfords are a solid choice (and definitely a lot better than wearing hybrid dress shoes), they lack the versatility of some other options.
Case in point: monk straps.
The big benefit of monk straps over oxfords is that they can be worn casually. A quality pair of monk straps can look just as good with a suit as they do with a pair of denim jeans or chinos.
They other great thing about monk straps is that not many guys wear them, giving you an opportunity to set yourself a part from the masses. I can’t tell you how often I get complimented when I wear my monk straps.
However, if the price point ($400 US) is a little too steep for you I recommend looking into a pair of Cole Haan Harrison Double Monks:
Although these are not quite as good as the Allen Edmonds Mora 2.0s they are still decent for their price point ($220 US) and have many of the same design elements of a more expensive shoe.
Most guys have a godawful choice in footwear during the summer season. It’s usually either a pair of dirty sneakers or flip flops.
Well, you can do them all one better by choosing a pair of classy driving mocs instead.
Driving mocs are just as easy to slip on as a pair of flip flops but look a million times better. These are a great option if you are looking to dress up a pair of shorts but they can work just as well with a lightweight henley and some chinos for a slightly more polished, laid back look.
The best driving mocs out there right now are being made by Jack Erwin:
The great thing about these is that come in just about every colour imaginable. The only drawback, however, is they are only available in suede. Damn.
Personally, I’m more inclined toward a leather driving moc. If you’re like me, then you might want to check out a great leather driving moc made by Cole Haan called the MotoGrand Penny Driver:
These are slightly more expensive than the Jack Erwin Parker drivers but still affordable at under $200 US.
Although Chelsea boots can be worn year round you probably wouldn’t know it as most men simply don’t wear them at all.
Well, their loss is to your advantage.
Chelsea boots are similar to monk straps in the sense that they can be easily dressed up or down and look just as good with your suit as they do with your favourite pair of dark denim or stretch chinos.
Here are some examples of the outfits Eli and myself have worn with a pair of chelsea boots:
The boots that you see Eli wearing in the above image are the Camroons by Ted Baker:
The chestnut brown pair I’m wearing with my twill jeans are from To Boot by New York (which are no longer available) while the black pair I’m wearing with my stretch denim are the Jack Erwin Ellis Chelsea Boots:
Personally, I’d recommend against buying anything by To Boot. I find that their leather is not of good quality and I’ve already noticed some signs of damage to my boots despite wearing them lightly.
Desert boots are definitely a summer boot but I’ve been known to wear them year around (as long as it’s not snowing or raining heavily). They have rich military history and are a great option if you are trying to ramp up your rugged aesthetic.
While there are tons of different options out there my favourite are the Clarks Original Desert Boots in Beeswax:
These are beautiful desert boots that will look good with the majority of your casual wardrobe. They are also relatively inexpensive (less than $150 US).
It’s often said that every great outfit starts at the feet and I couldn’t agree more. The type of footwear you wear says a lot about you as a man. Are you detail oriented? Are you fastidious? Do you have a sense of pride or class?
The 4 footwear options I’ve discussed above will absolutely set you a part from other men. I highly recommend looking into some of these options if you are interested in taking your style to the next level.
As always, here’s to looking sharp!