1. You can picture Larry David wearing your sneakers.
Some people can pull off “Cool Dad Style.” Chances are, you are not one of them.
Instead: trade your staid cushioned insoles for a quality pair of brown leather boots or oxfords.
Chukkas, Red Wings, those hiking boots with the metal lace clips — whatever you pick, know that they require even less thought than your go-to sneakers because they go with EVERYTHING.
2. Your v-neck sweaters are moth-eaten and threadbare.
Helpful hint: clothing from the Old Navy sale rack were not meant to last a lifetime.
Instead: rely on a chunky fisherman sweater for warmth.
You will be cuddly! But also manly.
Helpful hint: LL Bean makes great fisherman sweaters, and if you’re on the small side, you might be lucky enough to save some $$ and shop in the boys’ section.
3. Your laptop bag is a relic from the dot-com bubble era.
Your laptop has moved on, yet your case is still the Windows 98 of messenger bags.
Instead: embrace the manbag, literally.
Sure, you might miss the padded laptop compartment and the patented velcro Bluetooth headset holder. But these bags look so good that they’ll even make your cargo shorts look sexy (don’t wear cargo shorts).
4. The coolest feature on your current wristwatch is Indiglo.
You might also be lucky enough to have a pointless alarm and the ability to withstand the pressure of 100 meters of water.
Instead: invest in a leather band watch.
You’ll have to start taking your watch off before showers but SACRIFICE. No pain no gain, form over function, etc. etc.
On a sidenote, Timex also makes very nice watches with classy leather bands. So you might not have to lose the Indiglo after all!
5. You’re frequently swimming in “blousy” work shirts.
Although don’t get me wrong — your roomy Chandler-channeling shirt is due to make an ironic comeback at any moment.
Instead: do your figure a favor with a slim-cut button-down shirt.
You don’t even have to tuck it in! It still looks good. J. Crew and Uniqlo are good, less expensive options.
And for crissakes, get a nice belt to go with them.
Tanner Goods makes beautiful leather belts that are just thin enough, with interest complementing metal details.
6. You own one scarf, and it’s made out of polar fleece.
Once an item of clothing becomes an “easy DIY project you can make in under an hour!” it’s time to move on.
Instead: throw on a fringed scarf.
No, really THROW IT ON. You will automatically achieve the perfect degree of dishevel. This single important accessory builds character like no other item of clothing can do.
Instead: dare to wear socks in a bright color or interesting pattern.
They’re really not as foppish and dandy as you might think. That tiny sliver of detail that peeks out below the pant break when you sit down is PURE DELIGHT and nothing else.
8. Your idea of “adventure” is leaving BOTH buttons of your tried-and-true polo shirt undone.
Your polo shirts are fine for summer, but hardly work as a “layering piece” for autumn.
Instead: come to terms with the universal truth that a plain striped tee goes under everything, from hoodies to sportcoats to sweaters.
9. You’re still trying to get mileage out of a $10 pair of Urban Outfitters wayfarers.
Instead of being a protective accessory for your eyes, they’ve really just become a symbol of a thing in your life you managed not to lose.
Instead: shell out for nice pair of tortoiseshell-rimmed sunglasses.
God is in the details.
10. Your jeans still have whiskers on them.
While Diesel was once a hot international men’s fashion brand in the early to mid 2000’s, it’s time to let go of those prized jeans you once spent upwards of $200 on. They’re unnatural. No superhuman could possibly create that many crease marks around their crotch area.
Instead: try a stiff pair of slim-cut dark wash jeans.
Skinny jeans are a thing of the past, and the form has settled on a nice, sensible, slightly-tapered cut. It’s practically Hegelian, so let’s just be thankful we are living in a new era.