I think that it is very important for the context of my answer to note that the University of Queensland is in Australia (and I note this for the hoardes of uneducated Americans that read this site who probably thought that Queensland was somewhere between Queens and Brooklyn).

I was going to begin by berating you for even considering wearing trackpants with ugh boots, until I begin my obligatory research that I do when responding to any of my letters and found that the first two links returned to me from google were in fact from Australia and New Zealand (which, of course, aren't the same country but are, in fact, closer to each other than they are to anything else on this planet), which leads me to believe that people might wear trackpants as formal wear out there in which case my initial reaction might have only been related to cultural differences and not so much to a horrible fashion faux pas.

Until I realized that you said "trackpants and ugh boots." You do realize that when you wear Ugh¹ boots you are wearing the equivalent of one entire sheep's worth of wool on each of your feet, right? It would seem to me that these boots should be worn only if the situation exists that you might lose your feet to frostbite, and then, only if you are dressed in a big puffy snowsuit. I don't care how comfortable they might be.

That said, I don't think you should ever take the opinion of someone who tells you to wear high heels with your jeans very seriously. While the juxtaposition of two disparate styles can be pulled of successfully in certain situations (for example the often seen punk stylings of fishnets and cuffs and studs on an otherwise conservative suit-type outfit), heels with jeans just look stupid.

One other interesting thing that I have learned in my discussions with lawyers² is that law school is pretty much the last time that you can wear whatever you want whenever you want. The law field, unlike the freelance web columnist field, still maintains some modicum of dignity³, which means that you'll probably end up having to wear something either "corporate casual⁴" or "business formal" in your daily life. However, being a lawyer will also mean that you're going to have the money to start spending on all the nice, fun clothing that you never could afford when you were a poor law student, which means that you're going to have all of this clothing that you'll only be able to wear on the weekends. A conundrum, to be sure.

But the truth of the matter is that if you dress well, you will feel better about yourself, you will exude an air of confidence and the boys will come running. If you are slouching around in the library in your trackpants and ugh boots, you can bet that the boys are going to be running towards the girls in the tight t-shirts and the Fuck Me boots. Not because they're called Fuck Me boots mind you, but because she would dare to wear something called Fuck Me boots.

I mean, come on, "Fuck Me" or "Ugh?" I thought so.

Reference:
Sheepskin boots
Everything2 Entry: fuck me boots

1. A bit of research in this area also shows that the term "Ugh boot" actually is derived from the "Ugg" brand of boots which became so popular that they entered the common vernacular as the term for the generic, much as "Kleenex" and "Xerox" have. According to New Zealand Sheepskin, "many people are also now searching for Ugh boots and we don't know where this has come from, except that it must be a spelling situation."

2. I am currently dating a lawyer. A rather well-traveled lawyer with a lot of clothing. I'm sure that she'll have something to say about all of this, and I'll just let her respond in the comments below because, well, it's my damn column.

3. I am not wearing any pants. I am only wearing boxers. True, they are Banana Republic boxers, but they are boxers never the less. Never briefs. Just so you know.

4. I recently started hearing the term "corporate appropriate" replacing the term "corporate casual" presumably to renew that sense of professionalism into the corporate world while keeping the office drones happy in their flexibility to not have to wear suits to work every single day.