Shoe Revolution PT. 2

Now that you know the 5 main categories of men’s footwear from Shoe Revolution PT. 1, you just need to know what to wear, when, where to get them & how to care for them.

What to Wear & When-

You need a minimum of 5 pairs of shoes:

1. Black Oxfords or Loafers

2. Brown Oxfords or Loafers

3. Sneakers

4. Flip-flops

5. Slippers

Brown & black for any formal or social situation. Sneakers to work out and run errands in. Flip-flops for beach, river or BBQ. Slippers for lounging. You can definitely have more for more specific hobbies, i.e. hiking boots, running shoes, but the above should be the minimum. This will make it so you are never under dressed.

I firmly believe any social situation (besides a backyard BBQ or trip to the beach/river) deserves a nice grown up pair of shoes. Think about this, even a modest example, you have a man wearing dark jeans and a V-neck shirt out to dinner. Now picture him with tennis shoes, what does he look like? A high-schooler? Maybe. A college kid? Probably. A man who doesn’t care? Definitely. Now think of the same guy with a pair of loafers or nice leather shoes, what does he look like? A grown-up! You may not believe me but that’s the way women see it.

Another problem men may have to buying nicer shoes, is that they aren’t comfortable. If you think that, you need to stop paying $50.00 for a pair of shoes. Nice shoes fit great & are super comfortable. Look at shoes as an investment, not ‘if these $50.00 shoes last 6 months, it will be a good deal.’ That is false, because you are not calculating loss of confidence, respect and care from yourself and others into that equation, which is important in a recession. You need to think ‘If I have 5 nice pair of shoes and take care of them all, they will all last much longer than 6 months and I will definitely look good for the next two years’ plus the immeasurable profit of high self-esteem & self-worth.

While the tradition of men’s footwear states that the simpler the shoes, the more formal, we Portlanders laugh in the face of tradition. The biggest fashion faux pas in Portland is, obviously, to conform. We don’t even use umbrella’s when it rains. The worst nightmare of a true Portlander is to look like a tourist in his own city. Tourists use umbrellas, so we don’t.

So here is how to not conform with shoes:  Instead of wearing Oxfords  to work or with a suit, try Loafers, mainly monk straps. Get Oxfords in a color besides brown or black to make them less formal. Instead of wearing sneakers to a bar, try Oxfords. They all go great with fun socks. These shoes will pair well with your jeans, chinos & khakis.

Outside of work, you can always find me in a pair of single or double monk strap shoes. And they never fail to impress.

Where to get Them-

There are 3 stores I love to shop for shoes in Portland.

The 1st is Nordstrom Rack. They are hit & miss & you have to do a lot of searching and trying on, but sometimes you can score there with big discounts. When a nice pair of $200.00 shoes are marked down to $120.00, it’s hard to say no.

2nd, Aldo in Pioneer Sq. Mall is a great place for cheaper very stylish shoes from $70-$90 with sales, you can also get some great deals here.

Johnny Soles downtown also has a good selection, I can always find something there I like. They have limited amounts and have nicer shoes so are more spendy, but locally owned which fills my Portland pride.

Honorable mention for Banana Republic, I have a pair of brown single monk straps and I love them, & I think they are coming out with a double soon, and you can get sales there too.


If you invest in new leather shoes and plan to run around town in them, puddle-skipping and such, I recommend going to Derek’s Shoe Repair and he can put toe & sole protectors on. This way the shoes won’t let water in and the toe will be protected for $28.00. Not always necessary for every shoe you get, but if you have made an investment in a more spendy pair, I highly recommend it.

Get your shoes shined. I go to Nordstom (sans Rack) to the shoe section and you can get your shoes shined like a boss for $5 (that includes tip, but make sure you have cash). You can also do it yourself if you want, I may get into that someday, but I don’t know how & there are tons of tutorials online to find out how to do it you can find if interested.