Quest for the wardrobe of my thirties

This year I had some downtime and finally got to pack up and donate my late father’s clothes. That also prompted me to look at my own wardrobe.

Some lurking observations grasped for the spotlight. My closet was full of things I hadn’t worn in years (or ever). What I did wear had degraded to jeans and conference t–shirts.

Learn up

For something that we do every single day wardrobe gets little organized effort. Even less so for men, with lower social pressure on them about it.

I didn’t wear things outright ugly, or shoddy, or cheap, or otherwise problematic. But my concept of clothes was primitive:

  1. Formal (suit), which I don’t need.
  2. Not formal, which I have jeans and tees for, right?

I started to read information online for men like me — looking to update their messy ways.

The most helpful resources were:

  • The Essential Man — short blog which stresses importance of neutral colors and good fit;
  • The Art of Manliness — a lot of articles and guides on basics of clothes;
  • Style Girlfriend — women’s take on men’s style, a lot of outfit ideas and discussing things.

I realized that my “polar” view of formality wrong:

  • there is a broad range of formality;
  • you can use same clothes in a more (dress up) or less (dress down) formal way.

I had confined myself to most casual and least flexible bottom of the range.

The other important aspects I neglected were:

  1. Fit, which I had realized when I started to exercise.
  2. Color/print, a lot of things I had I didn’t want to wear because of it.

So the steps I needed to take were:

  1. Figure out which style and level of formality is comfortable and functional for me.
  2. Clear out clothes that are useless to me.
  3. Buy clothes that fit my needs well.

While I had no need to go all the way to top of formal, I needed an upgrade from the bottom of informal.

Clear out

All clothes I had passed through a critical look and several questions.

If I hadn’t worn this in years, why so?

Some things needed fixes. Or be remembered. :) A lot were too old to be presentable or still be something I would wear.

Does this fit my body well?

With some time and actual effort I improved about judging what does and doesn’t fit me. Some things with poor fit I liked… hanging in the closet, but not to actually wear. I needed to shorten all my jeans for a perfect fit on length.

Does this work with the rest of clothes I have?

One of the most important lessons was that clothes in neutral look and color work well with each other. Anything bright or ornamented clashes with most other things. Especially other clothes of such kind.

Everything that didn’t pass got the attention it needed or packed up and donated away. This is more of a continuous process though. Some things that did pass initial clear I still get rid of.


After clear out I went over I had left. This gave me some general idea on what types of clothes I prefer and what brands work well for me.

In recent years many clothes brands postponed entering our market or left it.

After some research I settled on one of the large mall. Among other thing it hosts shops from same “network” which share bonuses and discounts.

I did the two “kinds” of shopping — targeted and exploring.

For targeted I made a list of basics I need to get or replace and shopped for them.

For exploring I wait for sales and make an effort to explore respective store inside out. Note that I don’t buy things because they are on sale. I still look for things that fit in with what I need. Sales make it easier to explore and look for items that are not a priority.

On the cost one big change was thinking in cost per wear. Cheap thing that I won’t wear is an actual waste of money. Something of good quality and flexible will see a lot of use for a long time.

Top things

While it is too much to go over everything item by item, some things made a quick and easy difference for me.

Plain t–shirts

I preferred plain tees before conference ones started to pile up.

Back to plain! They can be harder to find in a sea of colorful and trendy, but worth it. Quality cotton feels great and neutral colors are easy to combine with anything.


Blazer is a suit jacket without matching trousers. Modern blazers are available in more casual styles. It makes them perfect upgrade up a level of formal.

I have also discovered that blazer is very flattering item in an older age. More of those shoulders, less of that waist. Suits are menswear staple for a reason. Blazer gets you in on some advantages, without going all formal.


Trousers that are not jeans. If all you wear for years is jeans, anything makes for a refreshing and stylish change.

Challenging for me to find a good fit on these. But even first pair in staple khaki color added a lot of flexibility to the wardrobe.

Matchy leather

I put together two baseline shoes–belt–watch “sets” in black and brown. It is a minor detail, but it feels good and serves as a skeleton for an outfit. Pick black or brown, fill in the rest with what goes well with them.


Still a cave–dwelling work–from–home creature on an average day. But being out and about, changes I made to the wardrobe are a lot of difference.

It is easier to pick what I wear and it adds up together to a better put together looks. Day over day I can now switch through outfits, not different tees. :)

I almost fit in at the parties now.

I almost fit in at the parties now. With Sonja Leix at WordCamp Europe 2017.

Out at the conferences I gathered a lot of compliments for the changes I made. Both for the specific items (“Nice shirt/shoes/sweater!”) and the look (“You look different/nice/dapper!”). Which happened before never.


  • wardrobe is a skill which benefits from thoughtful learning and application;
  • informal to formal is a broad and flexible range;
  • have and buy things you need, get rid of everything else;
  • being dressed appropriately for your body, taste, and environment feels amazing.

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  • Leho Kraav @lkraav #

    Dude, you're completely on the right track. I'm not sure how far along are you on quality button-up dress shirts, but https://www.sharpanddapper.com/collections/shirt-stays was my recent discovery.
  • Andrey “Rarst” Savchenko #

    Got a couple of dress shirts, but not a huge fan of them still. Also tucking them in doesn’t really work with my waist. :) My favorites are henley shirts.
  • Tom J Nowell #

    I can attest to those, nobody should ever need to tuck their shirt in. Though I know them as shirt garters Also, a good top hat really polishes off a good outfit
  • mark k. #

    Just a big +1 for the post. Men just do not learn how to dress and contrary to stigma, even out of the several gay people I know, there are enough that if it wasn't for the "we do not need no fashion" general attitude over here, they would have been declared as a disaster area.