Category

This & That About Men in Dresses

This is where everything lands that does not fit into a single drawer: experiences from the office and business trips, thoughts on social norms, answers to questions from partners and small observations from everyday life. Many of these posts started as reader questions, such as how to step outside in a dress for the first time or how to handle curious looks.

If you are just starting out, read my first time in a skirt and heels in public. And if you are wondering where to find clothes in larger sizes, the overview Where to shop will help. The posts below are sorted by date, with the newest at the top.

Man dressed for a business trip in a skirt and heeled boots

April 05, 2024

Skirt and Heels on a Business Trip

A business trip becomes the perfect excuse to wear a skirt and boots to the hotel bar — and a reminder that nobody is watching as closely as you think.

Man wearing a summer dress outdoors

August 09, 2023

Wearing a Dress as a Man in Summer?

Body hair, social conditioning, and the marketing history of women's razors — a look at whether men can wear dresses in summer. Short answer: yes, obviously.

Man wearing a skirt, blazer, and blouse on the way to the office

June 23, 2023

Wearing a Skirt and Pumps to the Office?

The first time going to work alone in a blouse, blazer, and skirt — and how to bring up the topic with people around you without turning it into a big drama.

Man wearing a women's dress, styled for everyday confidence

April 14, 2023

Women's Dresses and Skirts for Men — Tips

A-line, wrap, and maxi dresses, kilts, pleated and pencil skirts, and how to handle compliments and pushback with confidence — a full styling guide for men.

Man wearing women's clothing, reflecting on his personal style

March 26, 2023

My own world as a man in women’s clothes

Hello World: the first entry in a project the author once thought unthinkable — a personal look at why he wears women's clothes and what this blog is about.

Man standing in a cocktail dress

March 11, 2023

My world as a man in women clothes

Hello World: the first entry in a project the author once thought couldn't be real — his own world as a man in women's clothes, and why he started this blog.

Man expressing personal style beyond traditional gender norms

January 27, 2023

Gender Bender

What does the term 'gender bender' actually mean, and why bending the unwritten rules of gender presentation is fine — as long as nobody preaches.

Business outfit with blazer and skirt for a hotel bar evening

December 19, 2022

Blazer and Skirt at the Hotel Bar

A quiet Monday night in a strange city becomes a lesson in self-consciousness, a bartender's wisdom about regret, and why the stares matter less than you think.

November 24, 2022

Trending Dresses for Spring 2023

An overview of the top dress trends for spring/summer 2023 — which fabrics, silhouettes, and colors are set to dominate the new season.

Man wearing a tailored skirt as part of a stylish everyday outfit

November 07, 2022

When Is a Man Allowed to Wear a Skirt?

The skirt was never purely a women's garment — yet in Central Europe, men who wear one still stand out and need real nerve to do it.