Ugg boots, knee-high boots, ankle boots, gum boots. You name them, I’ve worn them. Boots have become quite the winter staple as far as fashion footwear is concerned and I for one have been following this trend keenly for many years.

However, this season’s boot trend has caught me off guard. Should I or shouldn’t I invest in a pair of boots that are so incredibly high, and I don’t just mean the heel, that most of my leg is engulfed by boot?

This season’s boots are going where no boot has dared to go before – halfway up the thigh and dangerously close to the crotch. I can certainly see their appeal; they look sleek and sexy. But, am I the only one getting flashbacks of Julia Roberts leaning against Richard Gere’s sports car in Pretty Woman?

To put it bluntly, my dilemma is this: Are these thigh-high masterpieces fashionable or are they going to make me look like a working girl and not the legal kind?

Tired of procrastinating I decided to undertake some investigation. I hit the stores and tried on as many pairs of thigh-highs as I could get my hands on. Flats, high heels, suede, leather – I tried them all.

I came to the conclusion that unfortunately, with thigh-high boots, it’s a case of you get what you pay for. Cheap boots (under $100), are made out of cheap-looking synthetic leather and look tacky. If the boots were cheap, it’s disappointingly easy to tell. If the boots were expensive ($250 onwards) though, they looked more stylish and classy. And leather shoes, of course, last longer, are better for your feet and are more comfortable.

However, there is one major warning when it comes to considering the thigh-high trend.

No matter how much they cost, avoid shiny boots – even if they are leather. They can drastically fall from stylish to stripper in the style stakes in no time. And, unless you’re buying them for a red light, nighttime business purpose, it’s best to back away slowly.

If this high-priced winter wardrobe staple is going to put a break in your university student budget like it would mine, I strongly suggest you do what I did. Take your knee-high boots from last year and pair with some thigh-high socks in the same colour. It looks amazing and their $20 price tag makes them much ‘easier on the old hip pocket’ as my grandfather would say.

Plus, there’s less risk of looking like a ‘pretty woman’.

Fashionista Monique Ancora is a final year Bachelor of Journalism student at La Trobe University. This is her first piece for Upstart.