maninboots

I wear stilettos boots and still manage to achieve a not too feminine look to be fair

Thanks you’re really kind, think it does prove that men can wear heels and boots of any length without creating a feminine look

Well I’m here again to start the weekend, i actually engaged in a little conversation with the young female assistant, while she was preparing my latte she noticed me adjusting my boots and she said i don’t know how you manage those, i said these are only 31/2”” heels but to be honest I’ve started coming down a bit in height as I’m getting older, she replied no i can’t do heels at all but i did buy some nice flat boots from Birmingham the other day, i said great i do like flat boots too then as she passed me my coffee she said we’re so used to seeing you in heels i can’t imagine you in flats, i said trust me it does happen, thank you and want and sat in my usual seat, fairly quiet here at the moment but did enjoy the few minutes of conversation

Fair point

I don’t think the length of your jeans really matters to be honest, not much point wearing heels if you only want to cover them up, long boots especially are designed to be seen, i prefer to wear mine over my jeans so then it’s more a case of how wide the jeans are rather than how long

It’s a bit of a catch 22 situation, you want to practice and be comfortable in them before going out in them but you can only really get that practice by going in them, but you are realising that you can walk around quite naturally without people really taking any notice, I’ve been out and about in the bullring in Birmingham today, went into loads of shoe shops to try on all sorts of boots, was able to engage in conversation with some shop assistants and again nobody batted an eyelid, keep doing what you’re doing mate and before long wearing heels will become the norm for you

Well done mate, proud of you

I.m going to answer in the thread Excursions Of Heeled Steve, as I;m aware this might be getting off the topic of simply what new boots have been bought. She's supportive about it & certainly wouldn't bat an eyelid if I wanted to wear stilettos. I would say though that she would want me to be able to walk ok in them. She bought me the most recent stiletto ankle boots and so was encouraging me to wear them rather than discourage me. To be honest I think she's more likely to say why have you got them if you're not going to wear them. I must admit that my confidence is always bolstered when I go out in heels with her. She herself doesn't have many heels and tends not to wear them regularly. I'm still more confident with a lower cone heel but am making the effort to wear the stilettos. Tonight on the way home I called in and did some shopping in a convenience store wearing my clarks chelsea boots with an almond toe and a 3.5" stiletto heel. I walked from the carpark down the High Street, did some shopping and then walked back to the car. My legs did feel it though even though I'd only walked in them for 20mins . It made me realise that I need more practice in them. Still just got to keep at it a bit at a time Here is a picture of the boots worn for tonights brief trip. My Wife has just seen me browsing the boots on the TK Maxx website. Apparently she has already had a look and tells me there is nothing new in today. I think this probably means that she isn't averse to my heel wearing! I do like those clarks boots, tried them on myself not so long ago, found them quite difficult to get on but with my high arches i do struggle with boots without zips, even though I’ve recently brought my snake skin ankle boots i normally prefer longer boots which can be worn both under and over jeans or trousers and there is just something about the feel of long boots and of course the look

Try longer trousers that cover the heels so not so noticeable, then if you go with your wonderfully supportive wife also wearing heels then anyone hearing the clicks would just think it’s her, start with short trips, Costa would actually be ideal and just act natural as if you’re doing nothing out of the ordinary, remember first time is always the worst but once you’ve mastered the first time it’ll be onwards and upwards, let me know how you get on, I’ve got every faith in you mate

Really do like those, look really good on you with those jeans, is that about a 31/2” heels, should give a comfortable walk, ideal Costa boots mate

To be honest i do like wearing my flat knee highs of which i have a few pairs, i have some knee high riding boots with a back zip, flat heels in black leather with a tan band round the top, often wear them over skinny jeans for an equestrian look and you’re right they are nice and warm at this time of year

You can’t beat it to be honest, I’ve got a couple of people having really good looks at the moment, think it’s only a matter of time before someone says something

Well it’s been a long week at work so happy to be back here in another pair of boots, these were brought from a vintage and retro shop in Lichfield , knee high with a full length zip, about 4” western style heels and particularly like the little gold bits on the back of the heels and the toes, very 70’s ish, I’m wearing them over my grey straight jeans, not too busy in here yet but let’s see what happens over the next hour and a half, oh and did you spot the medium latte in the background

Great to see you getting out and about in your boots, the heels look great by the way, we don’t have to wear massive stilettos every time we go out, i enjoy trips out in some of my flat knee high boots just as much but I’m sure with time and extra confidence you’ll find yourself pushing those boundaries a little further and challenging yourself and by the sound of it your wife will be beside you supporting you all the way and there will be no shortage of encouragement from me aswell, keep it up and keep us posted with your pictures, most importantly enjoy yourself

We need to find a central Costa to us all and meet up, could be a lot of fun and we’d take the place by storm, might even give the more conservative heelers the extra confidence to progress with their heeling, something to think about