So the first two parts were a brief overview of some of the things you can wear, the main takeaway is to buy quality garments at a good price.

One can buy classic pieces but add a splash of colour, whenever possible.

Shoes and Accessories can take you easily to the next level.


I spend a lot of money on my shoes, simply because they last me a long time.

it is better to spend $500 on a pair of shoes with a leather sole that I can replace, than some “fashion” shoe with a rubber sole that you will have to throw away after a season or two.

My favourite style of dress shoe is a brogue, due to the fact I live in a cold climate I prefer a thicker sole. For those in a warm climate will prefer a normal sole. Again, I like the tan/orange colour that sticks out and matches with most things. – this style is timeless, I have a pair from a different maker which I grabbed for $180. I always like a bargain, I want to look like the boss but not pay boss prices.





I also like to have a pair of brown suede shoes, for a more casual look. I wear a slip on loafer, it is great for casual Fridays, summertime or going to warm locations.

The brogue and the suede loafer are great with dress pants and more importantly denim jeans.

For athletic shoes, I will not spend over $100 for a pair. I am a big fan of Converse Jack Purcell and All-Stars. You can usually find these on sale for around $50, which makes them a great investment. These you can wear casual or dressed up, which I have done a few times on a Saturday night out on the town.
For those that travel, you will notice a lot of ladies in Europe love to wear the white all-stars. I am not saying you must dress like a woman, but it will make you look fashionable in their eyes.

My winter boots are made by Red Wings, they are a American company based out of Minnesota. The good thing about these is that they are well made and a little pricey, so I don’t see many guys sporting them. I had to resole my pair the other day, I found a shoe repair that can fix them but for $100. I wasn’t impressed about having to pay so much to put a new sole on them, then I realized I have owned them for 6 years and the uppers still look new. I spend the money when I have it and take care of my stuff, I don’t usually have to throw stuff away.

Another style of boots which are en vogue right now are Chelsea boots and Chukka boots. Both are great additions to every mans wardrobe, see the example below. (Chelsea boot in brown suede – win every time) (Chukka boot in brown suede – very rich look)

As you can tell, I am a fan of British shoemakers, there are many shoe brands in North America that make similar styles. Aldo, Johnston & Murphy, TooBoot, Cole-Haan are a few that come to mind. These brands you can always find on sale, again make sure they have a replaceable leather sole and heel.

I hope I don’t have to explain that your belt should match your shoes. I personally wear a brown suede belt with suede brown shoes.

The next thing I have been experimenting with is accessories and jewellery.

No one is saying you dress like Mr T, but a little jewellery does lend a bit of spice to any outfit.

I wear a few beads around my wrist and different bracelets, leather being my favourite one. I do want get to get a chain for my neck, I think a bead necklace might have me looking like Fred Flintstone’s wife Wilma, LOL!

Silver rings are always cool. Gold, although richer, might be a little played out.

I also collect cufflinks, but I try to avoid dress shirts as much as possible. I am not a fan of wearing suits all the time but I do own a few nice ones. I may do another article about my feelings on suits, which goes against what others have stated.

Wearing accessories can be a difficult balance, you don’t want to overdo it like a female. Maybe one ring, bracelet and a nice watch should do the trick.

I also collect sunglasses, stay away from the Gucci and Louis Vuitton fashion stuff. A good pair of Raybans aviator make any guy look good, the gold frames with a coloured lens works well with dark skin. I also have a few pair of Persols, which can be expensive but you can find on sale at a outlet mall for a quarter the price.

The point is to show your individuality and have your own unique style.

Ideally, you want people to comment on your clothes. Guys hating and girls asking questions is always a good sign.

I have a client I have been working with upgrading his wardrobe. He has fallen in love with American Apparel thermal Henley long sleeve t-shirts, not really high fashion I know. He feels comfortable in them and they are pretty versatile.

He was in the mall the other day, some young 24 year old lizard (Ukranian/Asian mix) came out of a store and stopped him to compliment his attire. He struck up a conversation with her and gave her his email address, I wasn’t there and can only do so much.

Game lessons cost much more and take more time. 🙂

Please leave a comment and your thoughts.

I will be posting some pics of my personal style soon (by Rudebwoy).