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How to Build your Shoe Collection - Dapper Edition

How to Build your Shoe Collection - Dapper Edition

The most important part of any building is its foundation. Screw it up and everything is F’ed. The same thing is true for your outfit (especially your dapper ones). A quality shoe is the literal bedrock of your look.

By killing it with your shoes you can “sell” the look of less expensive items. In the same way, a sweet (even expensive) outfit can be ruined with cheap shoes. Shoes are the best place to invest in your wardrobe.

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Below is a cheat sheet for starting to build your shoe collection. Only move down the list once you have a “quality” pair of each previous item. Also check out my article on building a professional wardrobe.

You can have all of your dapper looks covered with 3 pairs of shoes. Each pair after that is of diminishing returns, but, make no mistake, there is no such thing as having too many shoes.

Remember, quality before quantity. Do not confuse quality with cost, stick to shoes with leather (not rubber) soles and try to stick to a Goodyear or Blake constructed shoe.

NEVER buy shoes where the “upper” is glued to the sole and NEVER EVER buy a square toed shoes. Glued shoes will not last, they are not an investment and share toed shoes are ugly and cheap looking. Those are universal truths!

Here is how I would recommend building your shoe collection:

  1. Classic Brown Shoe - Your best bet here is medium to dark brown cap toe oxford or whole-cut. This is going to be your workhorse shoe. It needs to be dressy enough to be worn with your suits, yet simple enough not to call attention to itself if it is your first quality dress shoe. Stay away from heavy broguing at this point.

Like these dark brown Gucci cap-toes.

Like these dark brown Gucci cap-toes.

2. Brown Slip on. These are going to be a little less formal than your number 1 brown shoes, but you still need to be able to wear them with a suit or a blazer/slacks. Add a different shade than your number 1 brown shoe, but don’t go too loud. Since this is only your second pair of quality dress shoes, they need to be versatile.

Like these brown Gucci slip-ons.

Like these brown Gucci slip-ons.

3. Black Slip-on or Oxford. Now that you have your basic brown shoes covered, add a black pair. Again nothing too crazy if this is your third pair of dress shoes, but you can start experimenting a little here.

Like these black Gucci slip-ons.

Like these black Gucci slip-ons.


Alright, now you have your basics covered and you get to start having more fun and start really adding more of your personality at this level. If you are just starting out (or are on a budget), it may take many years to get here, but that is okay. I am still wearing shoes that I bought 15 years ago (and they still get me compliments), so there is no need to rush it.

Also, there is no real order anymore, so we are going to go from a list to bullets now. Also, if you are moving into some trendier styles or experimenting after covering all of your basics, you can move to a rubber sole if you want.

  • Add a monkstrap. Single or double monk. I just love monkstaps. They just kick ass. To me they are sweet and they work with suits, sports coat/slacks and jeans and not too many guys are sporting them, so you will stand out in a good way.

I love monks! Black double monks by AceMarks and Brown single monks my Mannina Firenze.

I love monks! Black double monks by AceMarks and Brown single monks my Mannina Firenze.

  • Add a suede loafer. Go with any color you want. If you stay with a darker shade, you will be able to wear them with slacks (in summer) and jeans.

Like these brown suede loafers by Kennith Cole.

Like these brown suede loafers by Kennith Cole.

  • Add a dress boot. Once you really feel confident about your game, you can totally pull off dress books with a dapper look.

Like these black Chelsey boots by Gucci.

Like these black Chelsey boots by Gucci.

  • Add a cordovan/oxblood colored shoe.

Like these cordovan shoes by To Boot New York.

Like these cordovan shoes by To Boot New York.

  • Add shoes with transitional colors/patinas. These types of shoes get better with age and they always stand out. They are truly next level.

Like these bad-ass double monks from Zenga Couture.

Like these bad-ass double monks from Zenga Couture.

  • Add some blue or grey shoes. Time to have some fun here. These will not come out of your closet often, but you already have your every day looks more than covered, so rock them a few times a year.

Like these grey Mezlan kicks.

Like these grey Mezlan kicks.


Want me to help you up your Shoe Game?

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