10 Must-have shoes for Men

1. Oxford Shoe

The Oxford is a dressy shoe. It completes the classy look. Oxfords are often confused with Derby Shoes, but there are marked differences between the two(See the third pic below). Oxfords are closed lacing shoes, whereas Derbys are open at the bottom. When it comes to styling, the Oxford shoe is much more formal. These are the ones you see being paired with tuxedos, and a lot of times you’ll come across shiny patent ones.

Oxford shoes (the most formal of all varieties)

2. Derby Shoes

A derby is a perfect shoe for all kinds of casual events, semi-formal events. You can wear it with jeans and chinos, even suits. Although for very formal outfits, you should probably go with the Oxford. This one is good for date nights and semi-formal events. Derby is a huge favourite and a forever a classic among men’s shoes. Go for medium brown because it’s super versatile, not too dark, not too light and you can just combine them really well.

Derby Shoes

3. Blucher

A blucher exudes style while not being too casual. To identify the shoe, notice the shoe lace tabs are stitched on top of the throat area of the shoe. The second identifying characteristic of the shoe is the hockey stick shape of the lace tabs. The shoe is versatile enough to wear in almost any situation (other than for very formal occasions).

Blucher (with a separate, L shaped leather piece sewn on the shoe for laces)

4. Monk Straps

Monk shoes fall in-between your Derby and Oxford shoes. This is definitely an ultra stylish men’s shoe. The monk strap was originally designed as a much more durable and dressier alternative to sandals similar to those worn by European monks. These shoes remain one of the best shoes for men. From single to double strap, you’ll also find them with brogue patterns(Brogues are decorative perforations on the upper of the shoe). Though they had to find a proper place between being for formal or casual situations, styled right they can fit both occasions The rakish monk strap has no lacing but is instead closed by a strap and buckle, and is considered not as formal as a full Oxford, but more formal than a Derby.

Patent leather double Monk Strap

Style Tip: Pair them with a suit, stick to black and brown. It’s sleek and with no strings to deal with, the monk strap shoe looks seamless with well-hemmed trousers. Want a pair that can fit your denim days? Try them in different colored leather and suede. You can find monk shoes in royal blue, green, several shades of red to oxblood. Wear your bottoms cuffed and try printed socks if you want to be more daring.

5. Loafers

Loafers, depending on the material, can come off dressy or be very casual. Going for a nice neutral leather will help you compromise between the two. Easy to slip on and off, loafers are accepted and appreciated for having no laces and an easy design. The T-shirt and blazer with distressed denim gets a touch of elegance from well-made leather loafers and a statement pocket square.

Leather Loafers

Style Tip: Loafers are great for a smarter casual style. Try wearing them with a sports jacket.

6. Moccasins / Espadrille / Driving shoes

Moccasins- Comfortable and trendy, the suede moccasin was originally made of sheep pelt and worn by Native American tradesmen and hunters, who could approach their prey quickly and quietly with soft-soled shoes.

Moccasins (good for winters)

The Espadrille, on the other hand, is a breathable shoe that molds to the shape of the foot easily. These are casual, flat, and usually have a canvas or cotton fabric upper and a flexible sole made of esparto rope.

Espadrilles ( The versatile ‘Summer Shoes’ are made out of cotton fabric or canvas)

Style tip: Both moccasin and the Espadrille (see below) are nice alternatives to wear with suits when you need to be comfortable driving, traveling by air–where quickly removing and putting your shoesback on becomes important to pass through security checks and where comfort is key when traversing large airports with luggage in tote.

Driving Shoes ( It is basically a Moccasin but with rubber sole)

Driving shoes are leather or suede moccasins with rubber-grommet soles. These were invented for men who wanted extra grip while driving.

7.Chelsea Boots

Some of the best casual shoes for men include a reliable pair of Chelsea boots. Slim fitting ankles with an elastic panel create a smooth look that was loved by the musicians of the Swinging London scene. Even now, they’re still considered amongst the top cool shoes for men.

Chelsea boots

Style Tip: Since they’re slim around the ankle, don’t wear wider leg styles with your boots. Skinnier legs help show them off. With endless outfit possibilities, try them with your button downs, vintage-fit sweaters and even your most beaten-up pair of jeans.

8. Sneakers/ Plimsolls

Sneakers are an absolute essential to any well-dressed man’s wardrobe. They’re clean, classy and look great with a lot of your casual, even up to a little more dressy outfits.

Sneakers in white color

Plimsolls are light rubber-soled canvas shoes, worn especially for sports. Didn’t you wear in school? Yes, it’s better known as Converse. The name Plimsolls originated in England, whereas Sneakers in the US. Both the varietie have rubber sole.

Plimsolls or Converse

Style Tip: Sticking to tradition, style your pair of sneakers with shorts and t-shirts, roll up the sleeves of your shirt. You may even make them work with a blazer. Distressed denim will always work with Plimsolls. Cuff up your pants, throw on a light jacket and you’re set for Saturday.

9.Boat Shoes

Another ultra casual shoe for weekend gatherings. The boat shoe is a good option to wear on rainy days so as not to damage leather-soled shoes. There will likely come a day when you’ll need a rubber-soled sports shoe. Wear them out on the water or beach, get them wet and they’ll dry as your day goes on.

Boat Shoes

Style Tip: When you feel like you just want to run around in a v-neck t-shirt and shorts, grab your boat shoes or cuff some trousers and wear a button down.

A major issue you’ll run into with boat shoes is the super stiff leather. Breaking them in will happen with wear over time, but if you want to speed up the process get them wet. I know some of you are thinking “leather and water?!” Don’t worry, there are proper ways of breaking in leather with water.

10. Desert/Chukka Boots

Worn during World War II across Libya and Egypt, specifically the Libyan Desert, these boots were made to survive extremely harsh desert conditions and terrain. The sole ranges from its original rubber construction to leather now and the upper comes in a variety of skins and color variations (mostly genuine leather or suede)

Chukka boots

Style Tip: A minimal design works amazingly with tailored trousers or a sports coat to jeans and casual shirt. A go-to for inside and outside the office, you can make these shoes for work in almost every situation.

11. Athletic (bonus one!)

Not only can they function as your gym shoes, but they can be worn with your casual outfits, as well.

Athletic Shoes

Now that you know your essential footwear, what are you going to add to your collection next ? Do let me know.

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Shubha Joshi, AICI CIC

Shubha Joshi, AICI CIC

Internationally certified Image Consultant and Strategist | Behavioral Trainer | Speaker | Youtuber. Helping people enhance their Style, Behavior and Confidence