A Guide to Men’s Fashion: Here’s how to begin.

So you want to find your style and upgrade your wardrobe. Where do you start? Follow this guide.

12 min readFeb 24, 2022

1. Make sure you really know what you look like.

I am a software engineer. I have no professional need to dress well or look good. No one in my immediate circles and no interview really cares if I have good style or bad style, if I look put together or not. This is a blessing and a curse, and if you’re trying to build up your own personal style it is fundamental to step back and give yourself an honest assessment. Do these things:

Take a few mirror selfies.

Removing the clothing affords you the chance to see what your body looks like and how you can build on top of it, and while you could just look at yourself in a mirror, I find the process of taking a picture and then sitting down to look at the picture gives a degree of physical separation that allows your brain to more effectively consider the actual shape of your body, rather than the perception you build around your body through daily life.

Consider your posture.

When you look at yourself in the mirror, do you notice an anterior pelvic tilt, for instance? Do you see your shoulders are rounded forward? Does your head jut forward? It’s not important to build up to an “ideal posture” here. Rather, you do need to confront the physical limitations and tightness your job likely creates. For me, I sit all day in front of a computer typing. There are plenty of people in similar positions. If that’s you, you need to stretch. Which brings me to my next point.


If you have pain, say upper back pain or neck pain, google “physical therapy upper back pain” and watch some YouTube videos on stretches you can do daily to improve mobility and reduce the pain. While posture and by extension physical mobility is often under-considered when talking about fitness, particular in men’s spaces where the first step is usually going to the gym and lifting weights, it is hugely important to be aware of, not just for style but for long term health too.

Be aware of what you eat.

This is another form of intentional awareness in your daily life. Consider what you’re eating and if it makes you feel good. I don’t just mean “cake tastes good so I eat it!”, but I also do not mean “don’t eat any cake”. Instead, I’ve found that when I really slow down and consider what I’m eating and how it makes me feel, I’ve started favoring certain foods that make me physically feel good after eating them, like fish and kale. And with sweets, because I love sweets, can I get the same satisfaction from just eating a little bit? Splitting a cupcake? You can make the passive dismissal that defeats the joy of eating sweets, but you’re just wrong. You can choose to believe that, or believe that savoring half a cupcake makes you happier than eating the whole thing. Neither is grounded in objective reality, which is an important fact to come to terms with.

Measure yourself.

Using a tailor’s measuring tape, which can be purchased for like $3, get your body measurements down. For instance, I watched a few YouTube videos on how to measure myself for clothing and using my measuring tape found my relevant measurements, then compared them to standard measurements for men my height to see if they were wildly off (indicating I had messed up during measurements). For example, here are my rough measurements:

  • Head: 57cm
  • Shoulders: 43cm
  • Arm (Shoulder bone to wrist bone): 65cm
  • Back (Neck to tailbone): 57cm
  • Chest (Measured around largest part): 111cm
  • Waist: 93cm
  • Hips: 103cm

I also found sanity checking the measurements with the measurements of a garment you own useful. For instance, if a tee fits oversized on you and has a shoulder measurement of 19 inches and you measured your shoulders as 20 inches, maybe you measured incorrectly.

2. Organize and Inventory

So you’ve considered your body. Now time to buy new clothes, right? Slow down!

Don’t buy new stuff just yet.

You might have the consumer itch to go out and buy new things. Oh, the allure of online shopping to pass the time. Don’t get trapped into the cycle of buying things your think look interesting or cool or fun or whatever piques your interest at the mall. Oftentimes, you’ve got a lot going within your closet already. So step back from the urge to buy and instead organize your closet and itemize what it is you have.

Marie Kondo your closet.

I started by going through all my clothes and deciding which items had I not worn in the past year. That’s the first cut. I donated or sold these clothes. Next, I looked through clothes that didn’t fit quite well. I brought these in to the tailor, getting two or three items at a time tailored to my current sizing. Not exactly the Marie Kondo way, but the core idea here is to thin out what you currently have to things you really want to keep.

B-b-b-b-b-but… I like my stuff. Ok! Even if you haven’t worn it in forever. What I do for things like this is box them up or vacuum pack them and put them somewhere out of the way, either in an attic or side closet area. Eventually, you might grow less attached to them and feel ready to pass on the items to new owners via donating or reselling.

If you are going down the path of reselling items, here’s what I recommend:

  • Local ‘Select’ Thrift Stores. We’re talking the Buffalo Exchanges, Lo-Fi Vintage Clothing, where all the cool kids go to shop on their days off type places. Usually you can bring in your clothes and they will tell you which they would be able to take and how much you could get for each of the pieces. Good for making a little bit of cash and getting things off your hands quickly.
  • Online resellers. My favorite apps are Grailed, Vestiaire Collective, Depop, and TheRealReal. These are also going to be important once you start buying new clothes. Good for making the most money from your clothing, particularly if you have high-end / interesting pieces.
  • Goodwill / Value Village / Basic Thrift Store. These places simply take your clothes as donations. I use them as my last line, since they’re guaranteed to take all of your stuff and they’ll just do it. Good for getting rid of your stuff quickly if you don’t care about making any money.

Inventory what you have.

For this step, I went back and forth with a bunch of different tools. First I tried making an excel spreadsheet. Then I tried just photos saved to an album on my phone. Finally I found that the system that works best for me is:

  • Take pictures of all the clothes against a solid contrasting background.
  • Use a photo editor to roughly remove the background. I used Photoleap and Gimp.
  • Add the items to Stylebook (an OK iPhone app, costs less than $5… if that offends you, stop trying to find a free app for everything. It’s 2022.)

In Stylebook, I’m able to drag different items together and create “outfits”. I’m also able to upload my measurements so I can easily reference them whenever shopping.

Screenshots from my Stylebook closet

3. Fill the gaps.

Ok, the foundation of a good entrance into fashion has been laid. You have gotten in touch with your body, you have organized and refined your closet, and you are now probably itching to buy some new things.

Pick a color palette.

Before buying, you can make the mistake of creating more chaos by introducing what I like to call “closet non-sequitors”. These are clothing items that you might love, but that don’t have full outfits that can be built up with them from your current wardrobe. Often times I find this is the result not of sizing or fit but color. When shopping it can be easy to forget color and how it will match with the rest of the pieces you own. If you’re good at this, and good at understanding color theory and how to create different vibes using different color palettes and combinations, amazing. Gold star. However, if you are reading this you probably need some guardrails. My strategy when getting into fashion more seriously was this: buy black or neutral toned pieces.

Ultimately, buying black clothes or neutral colored clothing won’t make you into a goth vampire. Stop worrying about that! (Or if that’s what you’re going for, add some silver jewelry for the right accents.) Here are some of the benefits of black clothes:

  • They match with other black clothes.
  • They give room to highlight any more colored pieces you have in your wardrobe.
  • They help mask curves in a flattering way.

For instance, I bought a black hoodie from Pyer Moss that I wear constantly. Why? It fits well, it is simple (only a small white text logo on the chest), and it goes with most things in my closet. I can wear it with jeans, or with sweats, or with black slacks, or white joggers, and add a hat, or a beanie, and choose between almost any of my shoes. In short, it’s a garment that is highly functional for my current style and needs.

Here are some good examples of black colored clothing that will get a lot of use and bang for your buck:

Uniqlo Airism Tee
Blundstone 510s
Pyer Moss Black Cropped Hoodie
Naked and Famous Black Denim

Find the gaps in your current wardrobe.

I like to approach buying in a few categories:

  • Core Pieces.
  • Accent Pieces.
  • Statement Pieces.

Core Pieces are the staples you would wear every day. Simple T-Shirts. Jeans. Shorts. Socks. Underwear. Undershirts. Button Down Shirts. You likely already have a good amount of these already. Maybe they don’t look great, or don’t fit your current color palette.

APC New Standard Denim (left), Uniqlo U Crew Neck Tee (right)
Church’s White Sneakers

Accent Pieces are things like necklaces, jewelry, belts, socks, bags, hats, etc… Things that fit around the main pieces you are wearing but give extra necessary accents to any outfit. Here are some examples of accent pieces:

  • A good pair of white Nike calf socks.
  • A hand-knit beanie from your grandma.
  • A black belt.
  • A vintage briefcase.
Example accent pieces: Black canvas belt (right), white Nike socks (left)

Statement Pieces are pieces that could be a simple accent or a core item, but because of their “loudness” or simply their aesthetics, they are making a statement by wearing them.

Example statement piece: sacai MA-1 Bomber

Typically, you want to avoid overcrowding an outfit with Statement Pieces. It is like muddling a story with a bunch of unnecessary and superfluous details to the point the reader is woefully lost and overwhelmed.

Sometimes you might want that. A GG Gucci belt with a Gucci tracksuit and an Off-White shoulder bag. There are no wrong or right aesthetics or styles! Remember that!

But there are wrong or right aesthetics for you. And, importantly, what is your ideal style can change or shift over time! People change! You change! So even if you think you know what your aesthetic is, recognize that it will shift and move and it’s best to learn how to grow and change your wardrobe with it. I like to use the following rule of thumb while shopping to fill gaps in my wardrobe: Buy core or accent pieces. Create full outfits of these pieces. Then, consider which statement pieces to add, since oftentimes the statement pieces are tied to a specific aesthetic you’re going for.

4. Grow into new areas.

This is where you should look at statement pieces. Explore! Take risks! Buy things and try things that you wouldn’t typically wear, or that you might consider “weird”.

Why not? If you don’t like a piece you try on or buy, that’s not the end of the world. But the most limiting thing you can do at this stage in your journey through men’s fashion is only buy “normal” items. Because what is normal? It’s just the rut you are comfortable in.

Here’s an example. One statement piece I recently bought was a short sleeve button down from the brand Pleasures:

I saw a post about it on Instagram and I’m a sucker for Leonardo DiCaprio’s vibe in Romeo and Juliet a-la Venice Beach. I checked the price and I had the money for it.

Then, I looked in my closet. There’s nothing in my closet that is really similar to it. And the colors are loud. It’s a risk to wear! But it looks really cool to me. I could imagine wearing it during the summer with an undershirt and shorts, to a party or out riding my bike. I did have some core pieces — shorts, socks, shoes — that could be built around this statement piece. So I knew if I bought it I could build good outfits with it. Notice all that’s transpired before I clicked buy! I…

  • Decided I like the piece.
  • Decided I could look good in the piece.
  • Decided I have room in my closet + the money to buy the piece.
  • Decided I have some core items in my closet already that could be built into a few different outfits centered around this piece.

I didn’t stop at liking the piece, then buy it. I’ve learned and grown from the times when I used to do that! Take my advice. The due diligence that goes into considering a piece can prevent you from making unnecessary and disappointing purchases, saving you a lot of disappointment and headache over time.

But, I’ve done my due diligence, I have checked off all the steps I needed to do before buying the piece. The last step before buying is deciding on a size.

Typically I compare my body measurements with the measurements for the piece, and compare the measurements to a garment I already own too. But sometimes life isn’t that simple. The website didn’t provide measurements on the piece unfortunately, so I have to move to my second strategy. I thought through the typical sizing of short sleeve relaxed button downs I own. Usually I am between a L and XL. Because the vibe of the shirt is very relaxed and fun, and I wanted to wear it out doing fun things, I want it to fit relaxed, and I know that if it is too tight I will not wear it. Therefore, I decided to go with the XL size, since even if it was oversized, I would prefer that over a shirt that is too tight.

After all this, I got the piece in the mail and tried it on. It looks cool and I’m ready to pull it out during the warmer days to come! I was right, it does fit oversized, and I could have probably been good with a Large, but the XL oversized look means I can wear it very loosely or unbuttoned over an undershirt. Overall, I’m happy with the purchase.

5. Stunt on your friends.

You’ve done it all! If you follow through on everything I’ve written, you’ll be in a very healthy space, fashion-wise. You know what looks good on you, what you like, how to shop for yourself, how to organize and maintain your wardrobe, and how to experiment in new areas. All this work has rewards. You look good! People might comment on your fits. What’s key is that even if you don’t get the external acceptance or praise you are hoping for, remember that your style and your fashion are ultimately about making you feel good.

If you are struggling to be self-confident and rely on others to validate your feelings and eagerly watch Instagram’s notifications to see if people like the picture you just posted of yourself wearing Off-White Jordan 4s, stop. Just go to therapy.




Software Engineer passionate about the future of cities. Currently building libraries for Azure IoT.