Does anyone else feel like a man in drag when they put on heels or makeup?

[MrsJamin]

Because that's exactly how I feel, I don't feel feminine enough to wear these things, and that people would look and laugh at me for even trying. Just put on the shoes I got married in and I just look and feel ridiculous. I'm going to a party tonight and just feel like I can't get out of my jeans and converse. :(

You might not be aware of 'style personalities' but they do exist and that's why some people wear certain clothes and look great, but others try the same thing and look/feel awful. It's a mixture of your actual personality, likes and tastes, and your body shape. When you know what style personality you are, it makes a lot of stuff fall into place. You sound like a natural, and you won't look right all dolled up, you need to stick to simple youthful makeup. There are quite a few websites which explain this - some easier to understand than others, but if you have a google, you might find something helpful

Yes MrsJamin! I hate heels and heavy nakeup - give me jeans every day and a swipe of eye liner and I'm done

I do but I still wear them. I'm 5ft9in and quite overweight so I always feel massive even though they suit me more than jeans.

Make up no, because I'm good at applying it and am well practised but heels are another matter, I look like Dick Emery

I walk like a man in drag when I put heels on actually I have seen several transvestites more nimble in heels
I don't own make up apart from a lipstick I bought over a decade ago.
I just don't feel comfortable all dolled up and have a much better time in trousers and a top than in a dress and heels.

I cannot walk in high heels but now at 48 I've just about (I think) managed nice make up - without the man in drag effect. I know exactly what you mean though. I'd love a link to those style personality websites if anybody knows a good one.

Me! I dread going to occasions where there is a dress code, I never feel comfortable at all.

I simply cannot walk in heels and don't understand what you are supposed to do with half the make up products you can buy.

I try to focus on getting my hair right and half heartedly attempt the rest!

Me too. I also dread occasions where I need to dress up.. I don't ever wear skirts or dresses, I don't possess any makeup and I can't walk in heels. I always have to settle for smart trousers and a nice top and then I blend into the wallpaper :/

The total opposite. I feel like a frumpy bloke-esq lump if I don't wear make up, heels, figure flattering clothes.

Good job I like them!

I love getting dressed up in high heels, a frock and all the make up - it makes me feel more feminine than when I'm in jeans and boots.
The only problem is that heels make me taller than my DH ( which doesn't bother him, but it bothers me )so I don't actually wear them as often as I'd really like to

I can't wear eye makeup, other than light mascara, without looking like a drag queen. I've got an... aquiline and rather deepset eyes which doesn't help.

I do think I'd have been a better looking bloke than I am a female tbh. C'est la vie.

That should be aquiline nose.

I pefer jeans n small heels with a little bit of make up and nice top but my fella is a fab walker of heels he has more shoes than me and is a skinny size 12 so when out on the town i look like the frumpy girl !!

With makeup, "the full works" (i.e. eyeshadow, powder, striking lipstick etc) makes me look like a man in drag, but I don't look right with none on either! I'm late 40s. I usually wear foundation, blush, dark eyeliner and lipsalve.

I'm 5'8 and have recently started to feel like a tranny if I wear heels. I never used to and I haven't suddenly got taller! I still wear them but just lower heels these days