Manly Mondays: Shoes

Until around a year ago I wore exclusively Converse and would simply buy a new pair every year when the old pair wore out. Then I found this amazing pair of Justin boots at a local vintage store that felt like they were made for me. Since then I have been hunting down vintage shoes and boots. But I wont lie, finding vintage shoes and boots isn’t easy.

Why Go Vintage?

One word, fit. Vintage shoes (and new high quality shoes) are made mostly of leather (including the sole), which will stretch and break in beautifully. This is also one of the things that makes buying vintage shoes so difficult. You will often find shoes that fit, but were broken in by someone with a very different foot than you.

But it’s still possible to find good vintage shoes, and it’s possible to find newer shoes that still look old and are handmade of leather, many of which are still made in the United States. These often turn up at vintage and thrift shoes for fractions of what they cost brand new.


Boots are a great addition to your wardrobe, they are stylish enough to go with anything, especially jeans and tough enough to be worn everyday without worrying too much. I own two pairs of boots the vintage Justin cowboy boots and a pair of new Frye boots.

Cowboy boots are easy to find at vintage and thrift stores, costing fractions of what they do new (a very nice pair of cowboy boots will run between $100 to $300).  Just keep looking until you find a pair with a good fit for around $30 to $60.

These Frye boots cost quite a bit, $250 to be exact, but I know I will be wearing these for the rest of my life. They are made of leather, but have a Neoprene sole. The rubber sole is great because leather soles trend to breakdown faster in the rain (and it rains a lot in Oregon) so these make great fall and winter boots.

Wingtips and Dress Shoes

I have had the misfortune to only find one pair of wingtips that fit me really well.  They are newer Allen Edmonds and I love them to death. They are all leather and have a great look and finish to them. I see oxfords and wingtips at thrift stores regularly and they are not too expensive. I also have a pair of newer black dress shoes that I keep for special occasions.

What To Look For

When shoe shopping here are a few things to look for:

  • All leather. Leather shoes are like leather jackets.  You break them in to create a great fit. If a newer shoe has a leather sole it will generally say inside the shoe. If it just has a “Leather Upper” the sole is usually fake leather which will break down sooner.
  • Made in the USA or Italy. The highest quality boots and shoes are still made in the good ol’ US of A or in Italy.
  • Find a good store. If you are going to buy new, buy from a good local shoe store.  The sales staff at at these smaller stores are incredibly knowledgeable. I had a clerk who could tell I needed a pair of 10 1/2s and not 11s, just by the way I walked. They also tend to stock good brands of high quality shoes. So you can try before you buy.

In Portland, I love Louie’s and Johnny Sole to buy shoes at. If you want to look at some good shoe brands, look at Frye boots, which are still handmade (in Mexico and US) of leather are are stylish and tough. Allen Edmonds are all made in the US and they have a great clearance section on their website.

Shoe Care

Now that you are buying leather shoes you need to take care of them. This means polishing and in some cases waterproofing. I use Kiwi polish for my shoes and I treat my Fryes with some leather cream that came with them. Polishing is a simple process,

  1. Clean all the dirt and dust off your shoes, use a slightly damp rag or cloth.
  2. Evenly apply the polish and rub it in with a polish applicator or rag.
  3. Buff the polish with a polishing brush.  These can be purchased along with your polish. Sprinkle a little water on as you polish to add shine.

Polishing helps your shoes look good. You can also apply waterproofing and leather creams to your shoes to help keep the leather soft.

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