September 12, 2014
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.
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.
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.
Chukkas: These short boots (popularized mainly by Clarks) are a great starting point.
Chelsea boots: Think The Beatles circa 1964.
Workman’s boots: Red Wing Shoes have been setting the standard since 1905 – check out the “Iron Ranger” line.
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.
Monkstraps: Technically also a loafer, but a bit more refined and pairs best with a casual suit.
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.
1. Flip-flops and sandals should be relegated to the beach.
2. Running/athletic shoes are for the gym.
3. Square-toed shoes only looked good when arriving on the Mayflower.
4. Vibram Five-Fingers are for Burners and yoga instructors.
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…).
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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