I was desperate.
It was the day before my flight to Austin Texas for my 4-year Anniversary. We planned to do absolutely nothing outside of lounging at Hotel San Jose and eating tacos everyday. It was a much needed break, especially for me after making the huge decision to shift gears with my business.
There was one problem though.
Austin was hot and I had nothing appropriate to wear.
A recent closet purge rendered my wardrobe entirely shorts free. On my way back from my final pre-vacation gym session, I stopped by a local 2nd hand shop and beelined for their shorts rack. My relief was short lived when I realized that the entire short selection the store had were all cargo shorts.
There was no time to search for reasonable alternatives, so I sucked it up and picked the least depressing looking pair – a large camouflage print in a soft washed cotton, in style for guys circa 2010. I justified it thanks to the time crunch and the $6 price tag.
I’m not going to lie, they were comfortable. So comfortable in fact that I spent a lot of this past Summer in said dreaded camo cargo shorts (see photo above).
I was making the cardinal mistake that a lot of guys I talk to make – feeling like it takes so much more effort to look good. That if you want to look good, you had to “dress up” in a 3-piece suit, complete with a tie and oxfords lace-ups.
This is an example of “extreme thinking”
Like people who believe that in order to be fit, they need to work out in the gym for hours everyday, when a solid 30-minute session would suffice. It’s all or nothing, so they don’t try to begin with.
THE TRICK TO LOOKING AMAZING ALL THE TIME?
The horrid camo cargos became a piece of what I call my “Base Look”.
A base piece is that coat you always throw on to run and meet friends without thinking twice. They’re parts of your wardrobe that have turned into your go-to pieces. Whether you’re conscious of it or not, we all pieces that we make part of our base look.
Despite a closet full of amazing clothes, and knowledge of how to dress well, the camo cargo shorts became part of my base look. It was the only pair of shorts in my closet for the humid New York Summer. It didn’t help that I put in zero effort to replace it. No wonder I looked like shit and felt embarrassed whenever I walked out in public with them on! Luckily, it’s been cooling down in NYC now and I’ve since donated the shorts.
Don’t make the mistake I did. Here’s how:
The trick to looking really fucking good, even when you’re not really trying? Redefine what it means to “bum around”. Raise the standard of your Base Look pieces. Making stronger choices for your go-to pants, go-to jacket, go-to coat makes it nearly impossible for you to look bad. It’s hard to dress like shit if you have no shitty clothes to choose from.
So what makes a good Base Look piece?
Three Rules for a Great Base Look Piece
1. Focus on the Major Staples – A go-to pair of pants (or in the case for Summer, a pair of shorts). A solid jacket. A classic coat. A great coat can cover-up a coffee stained college sweater, even look effortlessly cool, but there’s no hiding camouflage cargo shorts. Address the major staple first, then worry about things like t-shirts or scarves.
2. Neutral Colors – The name of the game is versatility. You want your pieces to automatically work with almost anything you pair it with. So keeping it neutral (blacks, greys, navy, browns) is the best bet.
3. Appropriate for Work and the Bar – Another criteria for a solid Base Look piece? Having the ability to be both work meeting and bar appropriate. Of course, this depends on the dress code at your job. But the closer you can get to this rule, the better.
Let me give you a great example of one of my personal favorite Base Look pieces.
MY ONE SECRET WEAPON:
THE DARK CHARCOAL GREY DRESS PANT
If navy is the one blazer every man should have in his closet, then charcoal is the one dress pant color every man needs. The perfect amount of dark without going funeral black, grey but not too light where it feels like white, the dark charcoal grey pant pairs with nearly anything you throw at it.
You might be thinking if you were going to grab a pair of pants to throw on, it should be a pair of jeans. But if your job isn’t casual, it wouldn’t be appropriate at all. Remember Rule #3?
This is why I love the dark grey charcoal dress pant, it’s ridiculously versatile.
Get it as part of a suit and you have a complete outfit to wear to work.
Lose the blazer and oxfords, throw on a leather jacket and sneakers and you’re good to go to grab a drink and some dinner.
If this is the default pant of your choice when you don’t want to think about your outfit, it’s hard to mess up.
My personal favorite pair right now? The Italian Wool number from Suit Supply, one of my new favorite stores in New York City. Beautiful fabrics, great fits and hemmed perfectly thanks to an extremely knowledgable staff while you wait!
How can you beat that?
Here are 3 looks to show off the extreme versatility of these pants in any situation to get you started:
NAVY WOOL/CASHMERE OVERCOAT BY ACNE STUDIOS, TAVERN SCARF BY DRIES VAN NOTEN, BLUE OXFORD SHIRT BY J.CREW, DARK GREY WOOL PANTS BY SUIT SUPPLY, DARK GREY PIQUE HEAT TECH SOCKS BY UNIQLO, BROWN SUEDE DOUBLE MONK STRAP SHOES BY SUIT SUPPLY
POPPING INTO THE OFFICE ON YOUR “DAY OFF”
So you’ve planned a day off in the city but get that dreaded morning text: “Can you stop in for a minute?”
How do you say no when you’re the Boss? You get shit done! But you also don’t want to be running around doing post work in a full on suit, so you got a good compromise.
Black oxfords can be a bit harsh, but brown suede will soften and warm up your look, while giving you a bit more color. Double monks are a slightly more casual shoe than the traditional lace oxfords, and their military feel make you look even more Boss. The blue oxford shirt is a staple for the workspace, but you don’t want to wear a tie on your day off. Add a bit of color and pattern without going overboard with a beautiful scarf. Throw on a navy overcoat to keep it dark and professional and you’re ready to pop in the office for a quick meeting, then go about your day.
BROWN SHEARLING-TRIMMED LEATHER BOMBER BY ACNE STUDIOS, WHITE EGYPTIAN COTTON CUTAWAY COLLAR SHIRT BY SUIT SUPPLY, DARK GREY WOOL PANTS BY SUIT SUPPLY, GREY HEAT TECH SOCKS BY UNIQLO, BURGUNDY LEATHER SLIP-ONS BY COMMON PROJECTS
LAST MINUTE DINNER DATE
Last minute dinner plans at The Nomad? No problem.
Nothing makes a guy look more masculine than a properly fitted leather jacket, so swap out that overcoat and go for the leather. I love a good shearling/fur collar on a minimal bomber, it makes luxurious, letting you wear to places where a zipper heavy biker jacket would look out of place.
Leather slip-ons, particularly these by Common Projects in a beautiful burgundy, call out to the brown in the leather jacket without over matching, and take the white button-up and gray pant combo down a notch from business.
NAVY WOOL/CASHMERE OVERCOAT BY ACNE STUDIOS, BURGUNDY COTTON FLEECE HOODIE BY BURBERRY BRIT, DARK GREY WOOL PANTS BY SUIT SUPPLY, BROWN HEAT TECH SOCKS BY UNIQLO, GREY COTTON T-SHIRT BY UNIQLO, STAN SMITH SNEAKERS BY ADIDAS
SATURDAY DAY DRINKING
Whether its going out for some day drinking with the guys or elbowing your way through Whole Foods for some groceries, a true test of the dark charcoal pants is the ability to bum around on the weekend.
What makes this casual and dressy mix of t-shirts and overcoats work? Keeping it minimal and logo free.
A solid light grey t-shirt, as opposed to a black one, lightens the look to let you wear some minimal white sneakers. Almost any colored zip-up hoodie would work here as a pop color, but I love the sophistication a deep burgundy gives this look. An overcoat is a nice way to pull in the look and give it another dressy element to balance all the casual pieces, but the look works just as well without it.
Looking to get a pair of dark charcoal dress pants and not sure how they should fit? Check out my FREE guide below.