i am under 20 and have been (or am trying to be) modest for like, the past 3years - i have not worn trousers (which will start another debate in itself), sleeves above my elbows, low necklines (by that i mean not below an inch or so below the pit of my neck).
(note: i say only skirts but, a skirt in itself is not modest since we all know of mini’s, slits etc. but mine are always below the knee, nearly all being quite a way below the knee)
in the beginning, it wasnt so hard, since coming out of wearing tight jeans and vest tops etc i started to dress a bit more modest every couple of months until it has now reached the stage where i have gone all the way.
it got to a stage where my family saw it a problem because they agreed with me trying to dress modestly but said i was starting to look old in the process, and this caused many problems, well for me.
the reason why i looked old, was because, while i was becoming aware of how i dressed, i started to not care how i looked, and decided to give up my ‘fashion sense’ (it has not and will never go but i decided to separate myself from this for a few reasons)
now, you dont have to do this, it is possible to remian fashionalble and stil be modest at the same time, although…
i will say, your style will automatically change and you have to be willing to allow this for modesty, for purity, for love.
you can image me, wearing an extremely short skirt and a tight top to wearing long sleeves and skirts - a radical change but i now have modified my personal style.
as Dove said, layering helps… a lot!!! i have skimpy vest tops which i wouldnt even dare to wear around my house when people are in let alone on the street, yet i wear them underneath v-neck tops which i know, 100% that i will not take off if its hot, thus revealing the skimpy top.
i dont know where you are but it hasnt been very hot in england in the last few years but even still, i tend to wear thin cotton tops, and thin layers, e.g. tshirts and cardigans and when it gets really hot ill push up the sleeves. i just think to myself of all those in the really hot places but still cover up, how do they do it? if they can so can i? i often think of the sisters who continue to wear their habbit.
the best thing i can say is pray!!!
i remember watching the Pure Life on EWTN and Crystalina evert saying when she goes shopping she prays to our lady to help her find something.
i have a quick testimony (yes i realize this message is dragging on, sorry

) but i have always wanted a leather skirt of a good length and fit that i can wear when going out.
doing new years eve shopping the other day and low and behold, what do i find in the vintage section of london’s topshop, a leather skirt just as i had imagined, less than 1/2 price!!! Look to our holy Mother, not just for help but for modesty - check this out, this is what finally pushed me to dressing modestly
drbo.org/modesty.htm
to finish off, i do believe letting go of my vanity (which, at the time i didnt realise i had) was much to do with me embracing modesty which goes hand in hand with purity - “blessesd are the pure in heart for they shall see God” ((not to agree with the 1st comment though))
i am happy and can never look back at how i used to dress, but i need to keep on praying, fasting, receiving our Lord in the Eucharist and going to Confession, to give me the strength to continue this battle since it is a really deep battle; i seem to think i get it worst since i am in that age group and am being so counter cultural, but as the lady before said, even the older generation suffers.
Ave Maria