Style Guide for Startup Guys (Part 3): Don’t Forget the Shoes, Brother

September 12, 2014

6:00 pm

This is part 3 of a 4-part series, Style Guide for Startup Guys, an overview on style tips for all the guys in the startup world. Read the two previous pieces,  “(Part 1): The Hoodie is Dead” and “(Part 2): Ties Aren't Just for Bankers”.

Chances are you've been just as engrossed with this year's Mercedes-Benz New York Fashion Week coverage as I've been. If by some chance I'm mistaken, the one lesson to take from this year's runways are that hats are back in a big way. We haven't see this many fedoras around since Al Capone was running Chicago (well, perhaps maybe at a Magic the Gathering tournament). Floppy, wide-brimmed, and classically-inspired- this isn't a second-coming of the trucker cap; it's as if America finally realized that Johnny Depp hasn't just been pranking us for the last 15 years.

But enough about hats. This next segment is about shoes.


Allen Edmonds “Strand” Oxfords in walnut calf. The Macallan 18 of shoes. (Find a pair at Nordstrom's).

The easiest way to dig into this one is to form two lists: 1) acceptable and 2) NSFW.


Pointed or cap-toe “dress” shoes: Every man needs at least one pair of lace-ups or Oxfords. If it’s the kind of shoe you’d take to a cobbler for repair, then you’re on the right track.


The Stacy Adams “Montgomery” cap-toe lace-up shoe is a great and affordable option (via Stacy Adams/Macy's).

Wingtips/Brogues: The key point of differentiation is the decorative designs punched into the leather. Nordstrom's has a great selection of wingtips and brogues.


Cole Haan “Lennox Hill” Wingtip (via Cole Haan/Nordstrom). 

Chukkas: These short boots (popularized mainly by Clarks) are a great starting point.


1901 “Brent” Chukka boots (via 1901/Nordstrom).

Chelsea boots: Think The Beatles circa 1964.


Chelsea boots by Frank Wright (via Asos).


Someday, you might get as hip as The Beatles. Be hopeful.

Workman’s boots: Red Wing Shoes have been setting the standard since 1905 – check out the “Iron Ranger” line.


Red Wing 6-inch “Iron Rangers” (via Red Wing).

Loafers: Chances are that your Mom had you in a pair of these for Easter Sunday. Give them another shot – they’re engineered for comfort.


Robert Graham “Gansevoort” loafer (via Zappos).

Monkstraps: Technically also a loafer, but a bit more refined and pairs best with a casual suit.


J Shoes “Troop” double monk slip-on (via Nordstrom).

Casual slip-ons: Yes, as long as they’re in good shape and it’s a casual afternoon, you can get away with them. Vans makes the classics and even Hermes has their own interpretation.


Fancy Hermes line of the classic Vans slip-on (via HighSnobiety). Pretty hard to get your hands on nowadays – try eBay?


1. Flip-flops and sandals should be relegated to the beach.


Burnnnnn in the flames of Hell.

2. Running/athletic shoes are for the gym.

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Unless you’re this guy; he’s got it all figured out (via AlphaBetaPie).

3. Square-toed shoes only looked good when arriving on the Mayflower.


And, even then, they were just “meh”.

4. Vibram Five-Fingers are for Burners and yoga instructors.


You’ve got to be at least a little stoned to sport these… (via Wikimedia).

5. Boat shoes are fine in moderation, but daily use is reserved for guys named “Skip” and ex-frat boys who get way too excited about “Casual Friday” (like your author…).


The official shoe of beer pong matches and underlying insecurity.

After covering tops, neckwear, and shoes, we've arrived at the end of this Style Guide for Startup Guide. Next week, I'll go over general style tips to get you where you need to go.


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Jake Kuczeruk is the Co-Founder and CMO of Tie Society. Raised in Michigan, Indiana University graduate, and citizen of San Francisco- where he resides with his girlfriend and two cats.