Last Tuesday morning, I was getting dressed in my kitchen at 7: 47 am when I spilled coffee in my freshly laundered (otherwise-clean) basket of clothing all over myself. Specifically, all over my only clean button-down. When I was supposed to be at school twenty minutes later.
I almost guarantee you that I looked like crap that day. But here’s the thing: every day is not going to be perfect. Some mornings, you spill your coffee on your shirt right before you leave for work.
Your wife leaves for work before you wake up, so you don’t have anyone to help you make your outfit decisions. I’ve been there too, buddy.
We all have.
I spend a lot of time thinking and writing about how to look intentional. Especially when you’re in a rush. Over the last few years of experimenting with my style, here’s what’s worked for me.
This goes doubly for teachers – no kid in middle school is going to let you slide looking like a schlub. They judge you, mercilessly. Our students are our toughest critics.
It doesn’t matter if you work at Apple; if you walk into school looking like you slept in your clothes, everyone will know. Middle schoolers will notice. High school kids probably won’t care, but your 13-year-old mathletes WILL notice.
And it won’t be in a “hey wow he really knows how to put an outfit together” kinda way either. Trust me. The key is having good defaults.
Outfits that you know work well together, that always make you look intentional. Mine are generally dark jeans (or chinos) with a solid-coloured button-up shirt. Basic, but once you have those “standards” you can throw stuff on top or layer stuff under to make your outfit look slightly less basic.
Something I’ve realised over the last few years of wearing basically the same thing to school every day is that having good defaults feels a lot like cheating. Most people won’t know the difference between “thought about this outfit beforehand” and “made good defaults.” I have a friend who’s a salesman. Great guy but man does he dress boring.
He has like five go-to outfits that he wears every single week. On repeat. But here’s the thing about my salesman friend: he always looks put together.
Not flashy, not weird, just good. clean-cut outfits. His name is Mike. He always looks nice because he has three kids under the age of five, a wife, and a wife and kids who rely on his income to stay alive.
He sells mutual funds and life insurance, so he has to look nice but he’s always rushing in the morning and doesn’t have time to think about outfits. Or so he told me over beers one night. Mike told me he calls it “strategic laziness”.
He has five button-up shirts that he knows go with five pairs of trousers. “Five shirts, five pairs of trousers. I pick a shirt, then decide whether I want to wear shorts or trousers that day. That’s it.
Pretty simple.” Dude couldn’t have been more right. Lesson #1: Start With Good Defaults My first lesson (that took me far too long to learn) is that if your shirt is falling off of your body in every direction, no one is going to think you put in any effort dressing that day. It doesn’t matter if you wear fancy trousers and a nice jumper over that shirt, everyone will look at your horrible baggy clown shirt and think you didn’t care what you wore that day.
Years ago, I grabbed some random shirt to wear that didn’t look horrible but certainly wasn’t one of my “standards”. I caught a glimpse of myself in the bathroom mirror at school and immediately knew I was going to hate wearing this shirt all day. It didn’t look intentional.
I could tell by the collar- it hadn’t even fully unfolded in the wash-and-wear cycle. I went to target later that afternoon and bought three Goodfellow button-ups for around $20 each. Not cheap by any means, but a hundred times better than Walmart shirts.
The material is thicker, fits much better than Old Navy, and doesn’t look misshapen when I pull it out of the dirty clothes hamper. Same Jeans. Same trousers.
But instead of wearing a Walmart shirt that looked like a Walmart shirt, I was wearing a nice button-up that didn’t give any clues as to how I wasn’t wearing an outfit I put thought into. Lesson #2: Shoes Matter More Than You Think If you know you’re running late, and want to look intentional, grab the closest pair of trousers that fit you well and are clean. And when I say clean, I mean clean.
Not the comfy trousers you’ve been meaning to wash. Trousers that actually fit your body. This was a huge lesson for me.
I used to wear athletic jeans and chinos that looked amazing when I first bought them but started falling apart after two washes. They looked nice… for a few months. Once my trousers fit correctly, my outfits went from looking like I didn’t care to being slightly more put together.
Next is your shirt. Anything with structure will do. Doesn’t have to be ironed, doesn’t have to be perfect.
Button-ups are obviously my go-to for this but even polos work. As long as it doesn’t look like a T-shirt, you’re going to be ok. White or light blue shirts are your friends here.
If you have a blazer, sports coat, cardigan, whatever – throw it on. This is honestly one of the quickest ways to make any outfit look more intentional. I’ve got this really lightweight J.
Crew Factory blazer that I bought on sale for around $40 and it instantly takes any outfit I wear to school to the next level. My students actually asked me if I had a “meeting” the first day I wore it to school. If you’ve got the opportunity to throw a jacket on, do it.
It doesn’t even have to match or go “perfectly” with your outfit, it’ll just look more intentional. I keep a pair of clean leather trainers by my front door that I wear pretty much exclusively when I know I’ll be rushing out the door in the morning. They go with anything in my closet and are super comfortable.
Before I figured that out I was rocking some super worn Nike running shoes with jeans thinking I looked “casual”. Get a Watch (and Wear It Everyday) Watch goes here too. I’m not saying you need to drop $300 on a Rolex or anything crazy like that.
But grab yourself a simple watch that you like wearing. I love mine. It was around $50 I think but I love wearing it.
Solid colour, nothing flashy about it at all but it doesn’t look cheap by any means. Bonus Points if You Can Properly Roll Up Your Sleeves If your shirt needs to be tucked in, tuck it in. Don’t mess with that military style tuck (sadly I don’t know the proper term) where you pinch the excess fabric on both sides of your shirt and tuck it towards your backside.
Just cuff it and call it a day. Eliminates the big-bag look. Same thing with your collar- if it’s not laid down right, nobody is going to think you put any effort into your outfit.
Make sure your collar and shirt are laying however they’re supposed to lay (helpful hint: evenly!) and you’ll instantly look more put together. If you’re wearing a button-up and you have the time, roll your sleeves the right way. Otherwise, you can just cuff them like I mentioned above.
To roll your sleeves correctly, flip your cuff upwards once, then roll the rest of your shirt sleeve up until your cuff hits right below your elbow. Lesson #3: Emergency Tips When You’re Short On Time Hair – throw some water on it and run your hands through it. Hopefully grabs any stray pieces that would have otherwise fallen into your coffee.
I actually keep a little travel sized tube of this very cheap pomade in my car. Not that I use it everyday or anything… Smell – please smell good. Wear deodorant, obviously but I actually keep a travel sized bottle of cologne at my desk at school that I spritz every morning if I know I won’t have time to get ready.
Don’t wear anything too strong but just something to give you a little freshness.
My Routine For Whenever I Wake Up Late Took me all of two seconds to write this, and literally took me two minutes to throw together this morning. Alarm didn’t go off and I woke up late.
Y’all, I made it to first period and not one kid said anything about my outfit. Not one. Once you have those standards locked down for yourself, you’ll be golden.
Again, mine are usually dark jeans/chinos with a solid coloured button-up shirt. I can throw jumpers, jackets, button-down vests on top. Maybe a hat.
Doesn’t matter. Stand up straight, pretend you belong there, even if you woke up twenty minutes late and threw an outfit together while running out the door. You’ll look 10x better, I promise.
