Dressing like a boy – menswear for women

Three women in menswear
Women in Menswear

One of the lovely things about being female in the modern world is that we can wear trousers all of the time if we want to. We can pair them with shirt, jackets and flat lace up shoes, short hair, waistcoats and a moody look. These models look very feminine, but comfortable. I love that we have the choice. Personally I tend to wear masculine shoes despite a fairly feminine aesthetic as I like to be able to walk and run. Men’s wear can emphasise femininity too, and elements of traditional male clothing can stop senior women looking too girly.  I find it unacceptable that in this day and age men do not feel able to wear a skirt or dress. Sometimes a loose unstructured lower garment is just what we all want to wear. Many men drift around in dressing gowns that look like wrap round dresses, at home. Eddie Izzard has suggested,”Women wear what they want and so do I”, to explain his desire to wear dresses and nail varnish. The unisex trend of the 70s, and later the Metrosexual look,  implied men wearing more feminine fabrics, colours and styles.

1970s article on Unisex dressing
1970s unisex

And why ever not?

Tilda Swinton in navy suit and white shirt
Tilda Swinton

When women first started “borrowing” their boyfriends cardigans, jeans and shoes it was a fairly radical act of defiance. For comfort and style. Here is Coco Chanel. Although, in the 1920s and 1930s, wearing a men’s hat or tie, tailored trousers or a Breton top with casual pants was slightly shocking, it soon caught on.

A more determinedly masculine look was pursued by others. Katherine Hepburn, for example. She wore jeans in the 1930s when this was unheard of, and usually paired her tailor-made strides with flat, masculine shoes. She was an individualist, with a 5’7″ athletic frame and an angular face and bodyline. Just the sort of shape that looks great in menswear.

Katherine Hepburn in masculine blue suit
Katherine Hepburn

As well as women who want to wear the pants some of the time, of course some women want to look decidedly masculine. In response to the demands of women marrying women there are now many companies specialising in tailored men’s suits for women. It is a trend I think is worth celebrating. The charming image below is from lesbian wedding site A Bicycle Built for Two.

Emily and Rachel
Emily and Rachel

If you want to wear men’s clothes go right ahead. Here are a few guidelines that might be useful

  • male clothes look best on women with slim, straight bodies
  • generally women’s clothes need a different cut
  • unless you are very slim bust darts are necessary
  • women’s shirts look better when they are closely fitted – Thomas Pink have a good range
  • if you have a shaped, curved body then you may be better to take elements of men’s wear rather than going the whole hog
  • tailored trousers with a shirt is a great look for work, but consider a feminine element – belt, shoes or jewellery
  • masculine shoe styles or hats can give an edge to a feminine outfit
  • high-waisted tailored trousers will emphasise a willowy waist
  • consider a floppy bow, an undone tie, or a bow tie in pretty fabric
  • “pant suits” as done by Hillary are a bit naff – coordinating trousers and jacket are better
  • if you don’t want to look too androgynous wear make-up, feminine hair and earrings
    KD in waistcoat and jeans
    Boyish?

5 Responses

  1. I love this post! Endless choices for everyone. I prefer more masculine dress but it might be due to my height (tall). I’ve just never been one for ruffles and lace, I’ll leave that for others. Your vest is so smart, I’m glad you are wearing it, you have me convinced I need to make one too.

  2. The vest looks great with those pants and loafers!

    You make some great points about men being restricted. I honestly never think about it, in part because I think that good men’s clothes are so nice. In Italy I prefer the men’s fashion to the women’s, believe it or not, and to my eye the tailoring is often better.

    I pretty much flip between wearing feminine styles and wearing menswear styles. I often wear shirts with a princess line, but I also like fuller, less-shaped or straight, undarted men’s shirts – just depends on what I’m wearing on the bottom and the look I am going for. I remember a friend saying that she felt shaped shirts on women were a little bit too “news anchor.” I also love slightly masculine shoes. For the last couple of days I have worn tweed trousers to work, to show off the new masculine loafers I bought in Italy. I agree about comfort coming first, but I think they are also pretty chic.

    Oh and I also love Katherine Hepburn. I think she was the one who said, “If I always do what interests me, at least one person will be pleased.” 🙂

  3. I love this look. Jackets and vests are my favorite, mostly for the structure…..but I also admire the look, and feel usually pretty confident in it.
    I had a teacher who wore a skirt to class…… you get used it pretty fast. Its true about the housecoats, my husband likes to relax in one too. Makes you wonder why we are so silly about such things.

  4. […] sexuality and cross dressing […]

  5. Brenda Marks

    Great tips! I’ve been looking for masculine shoes (such as oxfords) since I’d like to be as comfortable as possible in the foot department. However, I’m still looking for something that is high quality with a good fit (for a wide foot).

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