10 Things I’ve Learned over the Last Decade of Dressing Well

I started getting interested in exploring how to dress better (whatever “better” means) a few years before this website came into being. At the time, I didn’t feel great. I felt like my clothes weren’t doing me any favors, and they were in part misrepresenting who I was and who I was working to be. So I changed. I wanted the drapes to match my mental carpet. Anyway, you might not think I dress “well.” That’s fine. Taste is subjective. But I think the following observations will resonate, whether you’re ultra-hip, or, super conservative.

 

#1. Clothes can give you power. They can also take power away.

Dressing well opens so many doors it’s almost unfair. It’s more than just confidence. People often assume you’re the best version of yourself, even if you’re not on that day. Being smartly dressed can also knock a social or professional bully back on his heels. All without saying a word. Dress like you should be taken seriously. BUT (and this is key) don’t look like getting dressed was the most important thing you’ll do all day.

#2. A well executed personal uniform (or three) is nothing short of ideal.

Variety for the sake of variety can be one way to define chaos. Don’t be afraid to embrace a personal uniform or three. Find a casual outfit that feels comfortable but still looks good. Then develop something that’d look great on a date yet isn’t too stuffy. Finally, build a look that revolves around a suit for more dressed up affairs. Replicate those three outfits over and over in various colors & textures, and you’re set.

Dark jeans, sleek boots, tailored sportcoat. Easy.
Plus, there are tons of other ways to execute this smart-casual uniform.

#3. Let the Fanatics have their “Thing.”

It’s okay to not “get” something popular. Like joggers. Or selvedge denim. Or absurdly expensive wrist watches. It’s also okay if you do, and you can’t quite explain to others why you like what you like. Just as long as you don’t scoff at others who aren’t in your camp. Once you do that, you’re toast.

#4. Despite fashion’s continuous change and cyclical nature, there are plenty of constants in the middle.

The slimness of suits and jeans. Pleats on pants. Jacket lapel width. Everything comes and goes and comes back again. Yet there’s a middle ground that stays oddly consistent.

Change is constant. Yet there are plenty of constants that rarely change.

#5. Value can be found at almost any price point.

There’s an old saying… “Buy nice or buy twice.” But that’s not always true. A $40 pair of Levis is 90% as “good” as some $200 pair of designer denim. And there are countless other examples that proves you can find great value for reasonable prices.

#6. People are dicks.

Colleagues. Family. So called “friends.” They’ll all give you a hard time when you start to dress a bit differently. Anyone that does that is saying more about themselves than they ever could about what you’ve chosen to pull out of the drawer that morning. Trust your gut. Time will march on, and you’ll be really glad you listened to your instincts.

Just grin and bear it. No need to get personal.

#7. Cotton isn’t all it’s cracked up to be.

Cotton is cheap, and it can be great for stuff that needs to be washed a lot (say, dress shirts), but wool is the fabric that wins every time. Also, the proliferation of breathable technical type fabrics within classic menswear has also been nothing short of a revelation.

#8. Dress for your life. DON’T try to win approval from overly critical strangers on the internet.

We’re all gonna die. And I’m all for leisure, but, the amount of time… real honest to goodness, above ground, heart beating, brain synapses firing time… that is wasted by some on the internet arguing over and hyper-critiquing someone else’s personal sense of style is just plain sad. They almost certainly don’t know you, where you live, and how you go about your life. Context matters. Those types are cut from the same cloth as the weirdos who plaster not just one, but 25-30 political bumper stickers all over the back of their car. Are these really the people you want to take seriously?

#9. Keep perspective.

Getting dressed isn’t curing cancer. Get a grip, or, keep the one you have.

Dressing yourself should not lead to a swollen head.

#10. Finding a good tailor, early, will save you immense time, money, and frustration.

This can be tough depending on where you live. And the first tailor you go to might not be a great fit. But find someone who you can develop a good relationship with. Someone who can gently steer you away from making a bad decision, and who can make you look like a million bucks for much less.

Clothes seen in this post, in case you care, working from the top down: Sportcoat by Suitsupply. Oxford by Ledbury (sold out). Sportcoat by Spier & Macky (sold out). Jeans by Banana Republic. Belt by Gap. Chelsea boots by Banana Republic (sold out). Shirt by Ledbury. Coat by Charles Tyrwhitt. Gloves by Orvis. Jeans by Banana Republic. Sportcoat by J. Crew Factory (sold out). Watch by Hamilton (sold out). Stability Ball via Amazon.