This is an attempt at codifying my personal style guide, in part so I can look back on it in a few years and see how I compare.
Please put on this beautiful David Mallet + David Bowie video: https://youtu.be/GA27aQZCQMk — Just keep playing it on loop.
I’m just gonna list off a bunch of requirements/rules.
All of these “rules” can and should be broken, but only once you know what they are and why they are. I put them in the same category of “rule” as “rule of thirds”.
I template most things from the base necessary layers: Tops, bottoms, and in the winter time outerwear. I’ll go through them one by one and list off required pieces under that category.
Tops include but are not limited to:
- Dress shirts
- Sweaters, cardigans
- A sport coat or blazer
Try to mix it up with collar styles when it comes to choosing shirts. Live a little. Don’t get too many plain solid color shirts. Ginghams are fun. Any pattern is fun. I’m really big into dark solid color with bright colored micro patterns.
Some good places for dress shirts are Bonobos, Club Monaco, J Crew. Uniqlo sells cheap shirts. They used to fit better, but they’re still okay.
For tees, the layer that’s touching your skin, fabric is really important. Light weight cotton is the norm, it’s breathable and it feels good on your skin. It’s absorbent though, so if you sweat a lot it will show (depending on the thickness and weave).
Polyester doesn’t absorb moisture, but oh my god does it start to reek faster than anything else on the planet. Don’t get a polyester heavy tee.
I like splits, maybe 80/20 cotton-poly, maybe 60/20/20 cotton-poly-rayon. I’m not a big fan of 50/50 cotton-poly tees, a lot of people are, though.
Some good places for tees are Uniqlo, Everlane, and almost any other shop on the freaking planet.
For sweaters, I honestly don’t have a lot because I sweat a lot and don’t need that outer layer. Everlane makes some nice sweaters.
- Jeans. At least one good pair of overdyed black denim, a pair of blue jeans.
- Slacks, dress pants.
- Shorts. I don’t believe in shorts for men, you might. Jean shorts are fun.
For my jeans, I always get mid-rise slim fit. For your jeans, feel free to go high-rise or flare or skinny fit or anything you fancy. Try on a bunch, see what you like. It’s your butt, help it look good.
Try to stick with colors that won’t restrict the rest of your outfit selections. I tend to always have two overdyed black jeans, one pair of gray jeans, one pair of dark indigo jeans, and sometimes I own blue jeans.
You can find decent jeans at a lot of places, ranging from Levi’s to AG Jeans. Bonobos has a lot of options too.
I like a pair of jeans with a curved waistline and some sort of stretchy fabric throw into the mix, only 1 or 2 percent stretchy material. I wear these most of the year.
You typically only need one of each of the following to go with different temperatures and temperaments. Outerwear includes:
- A weather resistant top layer (overcoat, pea coat, etc).
- A good leather jacket.
- A bomber jacket.
- One or more of the named jackets, e.g. MA-1, A2, Type-II denim
Pea coats (and overcoats) are self explanatory. You might need a parka or something if you live somewhere cold (like I do). Don’t live life without a good leather jacket. It’s no life.
I say “a named jacket” because I don’t mean a “military inspired jacket”, I mean a standard per-spec MA-1 (or a slightly more generally fashionable take), not a seasonal twist.
Once you know what a typical MA-1 looks like and what features it has, when you see flight jackets in stores you can compare them against the base model in your head and see if it’s trying too hard.
Lots of places make good outerwear. Don’t go too fancy with the coat, you don’t need to be walking around in a double breasted pea coat every winter day.
For jackets, Uniqlo always has a decent collection for cheap. I like Falcon Garments for custom made leather jackets, since it’s all custom made they do women’s cuts too.
This is actually the most important section. Shoes make the look.
Your shoes need to match, or slightly raise the formality level of the rest of your outfit. They should never be less formal than the outfit.
When going fancy with the shoes, don’t overstep the rest of the outfit. Don’t wear super formal shoes with a casual outfit, don’t wear super casual shoes with a formal outfit.
Get some nice boots. Get some sneakers or flats. Get some chukkas. Get some heels. Call it a day.
It’s easiest to stick with black, brown (tan and dark), burgundy (or oxblood), or a bright contrasting color (white). I don’t like shoes that have more than two colors on them, unless they really own up to it.
Don’t wear running shoes unless you’re running.
Get two pairs of suits. One gray, one navy. No patterns, no fun designs, no frills. You can do those later. Make sure they fit well. Visit a tailor.
Wool is a good material for a suit, linen is the standard. Some sort of micro pattern linen (like nailhead) is my current go-to.
Don’t wear a black suit unless you absolutely have to. Black is a really formal color. If you need to wear black, go black-tie and get a tuxedo. The only situation in which a black suit is appropriate for is a funeral.
Your shoes and your belt color should match.
When it comes to your jacket, shirt, and tie colors, use a color wheel.
Contrasting colors for jacket vs shirt, complementary colors for tie and jacket. Solid ties work well, but ties with contrasting patterns do well too.
It’s easier to wear a light colored shirt, since most of your jackets will be dark. Don’t wear a deep blue, but a cloud blue is perfect. Don’t wear a bright yellow, but a pale yellow can work. Increase the contrast between the shirt and jacket, especially if they’re similar colors.
Your tie’s width should match the width of your jacket’s lapel. Don’t wear a skinny tie with a wide lapel. But feel free to wear a skinny tie with a slim shawl lapel. It’s a good look, sometimes.
Lots of places to get decent suits. Two semi-reasonable priced options are J Crew (cheaper) and Suit Supply (more expensive).
Be easy on yourself. Reduce cognitive overload.
It’s a lot harder to pull off a monotone look than it is to pull off a look with two colors and an optional accent color. It’s super okay to wear all black.
The simplest way to match colors is by prioritizing contrast. Pick two colors, try to match everything in one of those two colors.
If I pick black pants, I might do a gray or pink top alongside black shoes. Or I might do a black shirt with a tan belt and tan shoes. See where I’m going?
Layers that touch are nice opportunities for contrast. The bigger the layers, the more likely I’ll contrast them. This means contrasting top/bottom more than bottom/shoes. Without contrast, it’s a battle against looking like all your pieces blend together as a sad blob.
When you’re wearing similar colors, don’t wear colors that are too similar but not quite the same. Indigo jeans, a slightly lighter shade of blue tee, a slightly darker shade of blue sneakers isn’t a great look. Neither is three shades of gray.
Contrasts can be loud or quiet. You can color block, or you can wear all black with a gray contrasting item.
You don’t need an occasion to dress up. If you work somewhere without a dress code, don’t be worried about being the most formally dressed person in the office.
Dress up to make yourself feel good. You have no idea how often I wear my favorite leather jacket inside my own apartment. You should see what shoes I’m wearing right now.
All that said, my morning routine for dressing myself looks like this:
- Shower. Don’t even bother dressing well if you aren’t practicing decent hygiene.
- Check the weather for the day (and if it’s going to rain / or if I’ll need a jacket, thanks Dark Sky)
- Look at my calendar, if I have out of office meetings I might need a jacket in times I normally don’t (rainfall between 10AM-2PM, for instance)
- Grab a pair of pants (I typically own 3-4 pairs of same cut/style in different colors)
- Match shoes with those pants
- Depending on the temperature, either put on a tee or a real shirt
- Throw on any outerwear if necessary
That’s it. There’s a bunch of mini “Should I contrast this color here? Should I go complementary colors with these two?” decisions being made in this steps, but hopefully you can pick up on those by now.
I strongly recommend having full length mirrors in every room and spending your morning routine dancing alongside to some music being played out of an Amazon Echo.
Are you still watching that Davids Bowie/Mallet video?