How I Use Every Piece in My Wardrobe... And Stay Coordinated With No Sense of Style

5/22/2019

You're probably on this site because you're considering a professional headshot. Well, knowing what to wear in your headshot is just as important as knowing what to wear in real life, so that's why I'm writing this post!

Let me first make this clear: I have never had a sense of style! But by doing a bit of research and putting some color-matching rules together (and asking a stylist friend of mine for a couple tips & tricks), I'm now fortunate to say I almost always look well-dressed when I go out. This article was specifically written to help people who HATE picking outfits (especially men) to quickly figure out what to wear and ensure they look good!

The entire process of picking out an outfit and getting dressed with my system takes less than five minutes

I LOVE systems and setting something up once so it saves me a ton of time later on (an awesome book I highly recommend on systems is called The Checklist Manifesto). Today I'd like to share a super simple system I built to ensure that I'm able to perfectly match my outfits and look great on a daily basis - all while feeling extremely comfortable & relaxed in my clothes - and using EVERY piece of my wardrobe.

So why did I create this system? Because I used to wear the most terribly mismatched outfits - sometimes so bad that my team would make fun of me and say, "What are you wearing? That looks ridiculous!" Because of those jabs, I decided to set up a system to ensure I never looked foolish again, especially since I am a photographer interacting with tons of clients and occasionally doing public speaking. I believe we all have to ensure that we present ourselves well since first impressions are constantly being formed about us.

Before - Somewhat Mismatched & Random

After - Much more stylish and fun!

So What Goes into Great Style?

My belief is if you want to look great every day, your clothing should be timeless. Following the most recent fashion trend might look good for a few months, but pretty soon you'll need to buy a whole new wardrobe because certain clothing items won't be popular anymore and you'll quickly look out of date (think crocs or bell-bottom jeans). I don't enjoy spending money on clothes, so I own just a few things that will always work, regardless of What's Trendy This Summer, etc.

To keep things simple, here are the three most important rules I follow:

Clothes need to fit properly. Clothes should generally be form-fitting, meaning the seams on the shoulders of shirts should be right near the edge of your shoulder, the waist should be somewhat tapered close to your body, and the sleeves should not be too baggy. Lots of guys should wear medium (or even small) instead of large size shirts. Pants should be the right length, meaning the cuff should just slightly rest on the top of the shoe, and they should be somewhat form fitting around your legs, not too baggy and not skin-tight!
Colors need to match. Make sure the colors you wear together actually go together. If you're color-blind, you can use free apps that tell you colors or you can ask a friend, and then just write the names of the colors inside the shirts or pants so you remember for next time. We'll discuss color matching in detail in the next section.
Feeling comfortable is a MUST. I used to look stylish at the expense of comfort, but I quickly gave up on style and went back to wearing loose jeans and sneakers every day because I wanted to feel comfortable. But eventually I realized I can have both! I love wearing Cole Haan shoes now because they look great but they are designed with sneaker insoles (even though many of them are dress shoes) so they are ultra comfortable. I also wear pants that stretch because they can be form-fitting while still feeling super comfortable (and they rarely get wrinkled).

Color Matching Basics

Since I'm generally terrible at matching colors together and remembering all the rules, I wrote a simple cheat sheet for myself that I keep in my phone. When I'm getting ready every morning, I just consult the little chart to ensure that the pants, shirt, shoes, and jacket I'm wearing all match. As a reminder, the entire process of picking out an outfit and getting dressed with this system takes me less than five minutes.

Below you'll find the cheat sheet. Just make sure that whatever colors you match ALL match together. For instance, if you wear something pink and decide to match it with blue, you can't then wear black shoes because even though pink goes with black, black doesn't go with the blue.

Important Note: I know some people reading this blog might think my list is inaccurate because it doesn't consider shading and patterns, etc., but I want to keep things simple. My belief is that it's OK to mess up sometimes, and then you can make a note for yourself if a certain outfit combination didn't work.

My Color Matching Checklist

White
Pairs well with everything.

Red
Pairs well with pink, brown, purple, yellow, white, tan, blue, gray, black, and teal.

Yellow
Pairs well with blue, red, black, tan, green, gray, pink, white, and teal.

Green
Pairs well with blue, purple, black, gray, brown, white, yellow, and teal.

Teal
Pairs well with green, red, blue, gray, tan, pink, black, yellow, and white.

Blue
Pairs well with green, white, red, tan, pink, gray, orange, yellow, red, teal, purple, brown, and plaid.

Purple
Pairs well with blue, red, green, white, black, brown, gray, and orange.

Pink
Pairs well with gray, blue, red, black, white, yellow, and teal.

Gray
Pairs well with more subtle colors of pink, blue, red, yellow, tan, green, orange, purple, black, white, and teal.

Brown
Pairs well with tan, white, blue, red, green, purple, and orange.

Black
Pairs well with white, pink, teal, red, dark green, yellow, tan, purple, gray, and orange.

Orange
Pairs well with black, brown, purple, blue, white, and gray.

Tan
Pairs well with red, yellow, white, teal, blue, gray, brown, black, and plaid.

Plaid
Pairs well with blue, tan, and white.

I hope that checklist simplifies the color matching process for you. As you probably noticed, I included plaid as a color, only because it often has numerous colors mixed together. I've found it's easiest to just wear plaid with blue, tan, or white because you minimize the risk of mismatching any of the colors (blue, tan, and white go with almost everything). If you're curious to learn what colors go well on-camera, you should check out this article: The Best Colors and Clothing to Wear On-Camera

Below I'll explain how I personally use my color checklist from above to take less than 5 minutes to pick an outfit and get dressed (with about a 98% chance of not making a mistake), but before we move on, I'd like to quickly add a list of DON'Ts. These are color combos you should avoid if at all possible (unless you're feeling very lucky):

Do Not Mix:
Brown & black
Red & green
Gray & brown
Blue & black
Green & pink
Green & orange
Purple & yellow
Red & orange
Dark gray with bright, intense colors

Those colors often don't go together and could get you into trouble. I generally stay away from them because I like to play things safe. If you're feeling more adventurous and lucky than me, try breaking the rules! You never know if you'll come up with something great... or fail miserably. My general rule is to stick to three different colors or less so things stay simple (white doesn't count as a color).

The only other thing to note is that you want to avoid wearing colors that are very close to each other (like blue pants and a blue jacket) because it will look like you tried to match them exactly but failed miserably. Either wear an exact matching suit or go two completely different colors so it's obvious you weren't trying to match them! 🙂

My cat thinking, "Why are you taking all these pictures of your clothes? Let me SLEEEEPPP."

How to Use Every Piece in Your Wardrobe Easily

What I love most about my new system is that I literally wear every single thing I own. No longer do I "80/20" my wardrobe where 80% of my clothes stay unused while the remaining 20% get worn so often that they literally fall apart. I'd like to share my exact dresser and closet system with you here so you see what I do (and then I'll make some suggestions if you don't want to follow my system exactly).

The first thing I did in order to set up this system was I looked through everything in my drawers and closet. I got rid of anything I didn't like or knew wasn't comfortable to wear (some of them I stored at my parents' house so I wouldn't need to pack clothes anymore when I visit them).
Next, I took all my hanging shirts and pants out of my closet and folded them. You'd be surprised at how wrinkle-free things stay, even when they're folded (and if they get wrinkled, buy and use a steamer - it's so much faster)!
I separated my cold weather from my warm weather clothes. I put all the cold weather clothes into two big bins that I now store at the top of my closet, ready to be taken down and switched when Autumn comes. By doing this, I freed up a lot of space in my drawers and closet.
Next, I arranged all my pants and shirts into drawers - all the long pants in one drawer, all my shorts in another, all my t-shirts, polos, button downs, etc. You get the idea. In some drawers, if I didn't have that many items (like shorts and t-shirts), I would put them in the same drawer (separate rows) since I only have a few drawers.
I folded everything in such a way to be visible from above so I can instantly see into my drawer and know exactly what each shirt or pair of pants is. Nothing is on top of something else (except socks). See the photos below.
I left only my suits, jackets, and super fancy clothing hanging in the closet - anything that absolutely needed to stay hanging or would take way too much space in the drawers. Everything else was moved to my dresser. See the image further down.
Once this organization was complete, I was easily able to start building my outfits for each day.

Image A - All my button down shirts (some sweaters in front)

Image B - All my shorts (some socks in front)

I'd rather have my clothes a tiny bit wrinkly from time to time and just use my wife's steamer when needed than never wear the article of clothing at all. I've found that when my clothes are in the closet, I rarely think to wear them since I keep most of my day to day stuff in my drawers.

I tend to work right to left (or back to front) in my drawers when grabbing new things, and whenever I do laundry I just put the clean, folded pieces on the opposite side of where I grab from. Slowly I rotate through every single piece in my wardrobe by doing this.

Note: If you always wear things from your closet, you can just rotate through items one at a time and put a small marker around whichever hanger you just took from so that you know to grab the next item in line the next day. Just move left to right or right to left.

My closet - now only holds suits, jackets, ties, and belts. No shirts or pants, otherwise I'd never remember to wear them!

How to Take a Plain/Boring Outfit and One-Up It

Once you have a pair of pants that matches your shirt and shoes, it's time to think about whether you want to make your outfit look more crisp. Here are a few tips that can take outfits from boring to snazzy!

Tuck in your shirt (I don't do this with t-shirts or plaid shirts though).
Wear a nice watch (not an Apple Watch).
Try using different color shoelaces (you can buy colored-shoelaces on Amazon).
Try wearing nicer-looking shoes.
Try rolling up the sleeves on button-downs. This looks great with a nice watch.
Wear a tie or pocket square. And try adding a tie clip if you want!
Wear shirts with French cuffs and cufflinks.
Wear nice sunglasses when you're outside (hint: smaller sunglasses look better on most faces).
Wear a well-fitted jacket that matches your outfit (or one up it by wearing a suit jacket or blazer - even with jeans).
Buy a cool belt that's a unique color like blue or beige (rather than just a brown or black one).
Wear dress socks with nice designs (and if you don't like how thin they are because they get holes, wear a pair of short black gym socks underneath the dress socks - it makes them feel much more comfortable & thick in any pair of shoes).
Make sure your haircut is looking good.
If you're a girl, jewelry is always great too.

How I Use the System to Get Dressed & Look Great
(in less than 5 minutes)

In this final section, I'd like to just give you an idea of my process, step by step, so you see how easy it is to use this system to figure out what to wear.

My pants drawer with some socks in the front. I grab the right-most pair of pants that matches the weather/formality.

Season: I already have all my winter clothes put away for the warm weather, but if I didn't I would need to make sure I'm wearing colors that are appropriate to the season - brighter colors in warm weather and darker colors in cold weather.
Weather: If it's going to be dingy and raining, I stick with darker, muted colors, and if it's going to be bright and sunny, I'll stick to more colorful colors.
Formality: If I'm going to a fancy event, I'll plan to wear something more formal, and if I'm just hanging out, I'll wear something more casual.
Start with pants. Knowing all the above, I'll open my pants drawer. Whatever pair of pants is furthest to the right I'll choose - unless it doesn't match the conditions above. For instance, if it's going to be a bright, sunny day and it's a weekend, I won't wear the pair of gray pants that should be next, or the black ones next to those. I'll just choose the blue jeans that are up third since they go with all weather.
Pick a shirt. Knowing the weather, I'll open either my long-sleeve shirt drawer or my short-sleeve drawer. Whichever shirt is furthest to the right is the one I'll wear, assuming it matches the color of the pants. So since it's going to be a warm and sunny day, and I don't have any important meetings, I'll wear a short-sleeve polo shirt. Imagine looking into the drawer. The one all the way to the right is black. That doesn't match blue jeans (or the bright weather), so I'll look at the next one, which is red. Cool, it matches, so that's going to be my outfit today, blue jeans with a red polo shirt!
Pick shoes & a belt. I usually try to match my shoes and belt unless I want to be experimental. Black won't match blue jeans, so I'll pick brown shoes. So now I've got brown shoes, brown belt, blue jeans, and a red polo shirt.
One-up my outfit. I don't want to tuck in my shirt since I'm going for casual, but I decide to do a few other things: I put on a nice watch that matches, do my hair, and pick out a lightweight blue jacket to wear since it's still a bit chilly this morning. I had previously thrown some tan laces onto my brown shoes which made them look more summery, and they look good. Finally, I'll wear some nice socks. Technically I can choose any color socks as long as they match, but I often try to wear a similar color sock to my pants, so I'll just grab a pair of dark blue argyle dress socks and put them on over a pair of short black gym socks so they feel really comfortable.
I'm done!

I've never worn this exact outfit before but it took me less than 5 minutes to put it together and get dressed. I'm happy because it matches and looks fine! You can see a picture below.

My goal is not to go overboard and be crazy and try to have perfect outfits every time. I'm sure some people who look at this outfit will have critiques. But what I know is three things:

I get to use every piece of clothing I own.
My clothes match fairly well every day and I make a good first impression.
I feel super comfortable every day, and I look good.

Those are really the only things I really care about.

And if you're interested in reading further, here's another article I definitely recommend: The 4 Most Important Things I've Learned from Age 20-30

If you have any questions, comments, or suggestions for me in this post, feel free to leave them in the comments below!