Rule #02: Low-Risk, Modest Reward

We assume that you are reading this list because you like to shop, but it's #143rd on your priority list - unless it's a holiday, birthday or anniversary. Since everyone is in the spirit of giving, you'll be scrolling through websites looking for great gifts for the family.

While your credit card is handy, how about grabbing a few items for yourself because you deserve it. If you had an amazing year, what better way to tell yourself thank you than a new pair of kicks? If you had a subpar year, what better way to motivate yourself to be less terrible than a new pair of kicks?

We hope your answer is always 'a new pair of new kicks'.

Shopping the Digital Highway

Rule #01 said to keep your kicks fresh with a healthy rotation. We understand how that sounds expensive when you're looking at your kids $200+ Lebrons, Yeezys or Buggin' Outs Jordans. We will definitely recommend going wild in the future, but we want to build a foundation for a successful portfolio before you hunt for unicorns.

Plus, like Buggin' Out from Spike Lee's classic 'Do the Right Thing', you aren't ready to have people step on your unicorns.

Buyer's remorse is real, so let's walk - not run - into building your collection. Start small and let that interest grow. The difference between looking like you're having a mid-life crisis and becoming fashion forward is pace.

Staying Under the Radar

Highway speed limits are there for a reason. You should only go above 75 if you know what you are doing. And if you're not in a hurry, why risk the danger or the ticket. Here we'll grab a few items that will get you there without whiplash or turning too many heads.

I'll spare you the low hanging commodities like Chucks and Vans because you can grab those any time. At these speeds you can stick to the basics or take a risk - like this Puma Clyde x Diamond Supply (US$65 at Rime NYC). We are going to go a little deeper today, so let's start digging.

Classic Roadster

No doubt you've seen a few off-white, vintage colored relics walking around and wondered how your yearbook photos made it back on the streets. Kicks like this Womens Reebok Club C Vintage (US$75 at Urban Outfitters) and the Mens Club C 85 (US$83 at Sneakers-N- Stuff) keep your style relevant without looking like you needed to take out a mortgage to do so.

No Frills

You can take your pick of basic 70's jogging shoes from Nike, Adidas, Asics, etc. While they all will work in your closet, our goal is to diversify your portfolio. Enter the Saucony Jazz (US$55 at Paragon Sports). Quite possibly one of the most no frills options we could serve up with a name that will let people know you can keep it fresh.

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Turn Up the Music

"I can't pull this off," is what you said to yourself when you saw this classic Converse One Star in hairy suede (US$58 at Converse). But before you break your thumb scrolling down to find something safer, just think back to that crazy convertible you rented in Miami that 'wasn't you'.

We don't recommend that you 'shine bright' everyday, but we do want you to challenge yourself at this price. You'll need this dosage to prepare you for what's to come later on.

*Here is where I'll note that my family still continues to eat from the table of Swoosh, but my recommendations won't be swayed by loyalty or vengeance for one company or another. Your style is all that matters to me - your sneaker fiduciary.

Check Your Mirrors

When Shawn Carter and Roc Nation joined Rihanna at Puma, the brand's authenticity continued it's ascent. Join the club. And you don't have to go Lilac to be fresh.

To be honest, there's not much to dislike on the shelves for women at Puma, but you can pick up the Basket (US$65 at Asos) just to get your feet wet. While this execution is definitely unisex, the Fenty inspired bow laces and platforms that are available would be great fashion choices if you're game.

Old Roads

While you could opt for Daniel Arsham's Future Craft iteration with the Adidas Consortium team, we suggest you try his more attainable earlier exploration (US$65-$90 at Flight Club). Your obvious worry is that white canvas will immediately get dirty. Totally okay. These beauties will age well, you'll be able to discuss modern art and your kids will wonder how you know about Flight Club. All good things.

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Slip & Slide

The original online sneaker brand, Greats, delivers premium classics from Italy. Their base model - the Royale - was replaced by Allbirds as the tech-hipster's go-to sneaker, but they still deliver amazing product for under $200. And every now and again you can find something fall to a price that you can't pass up. The Womens Wooster (US$71 at Greats Brand) is an easy-to-wear model that you'll have to force yourself not to wear everyday.

Other Side of the Street

This is not your standard issue sneaker but you'll be able to casually drop the name Boxfresh for cool points at the pub. The UK brand Boxfresh had a modern take on the old man sneaker in the form of the Rily (US$56 at Extra Butter). Now you can watch Liverpool v ManU in style.

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Time to Floor It

You've been patiently scrolling below the speed limit, but let's be honest: you didn't get where you've gotten in life sitting in the slow lane for the entire trip. And if you think you're going to score the Air Max 1 Premium in Suede (US$130 at Nike) for under $75, you've been sitting in the garage with your Tesla running for too long (good thing it's electric).

You've probably already spent $1000 on gifts that will be forgotten before you pay the bill. So click away.