It’s the time of year when temperatures are dropping and the now four-year-old debate on the merits of Ugg boots begins to rage once more.

This morning I was walking to Anderson Hall with three of my residents, and our conversation quite naturally turned Uggs.

Melissa got her first pair of Uggs after seeing them on Oprah’s Christmas special in 2003. Marcella’s parents weren’t willing to spring for the real deal so she owns a pair of “Fuggs,” or fake Uggs. Dena wouldn’t touch any version of the boots with a ten foot pole.

While I’m not a classic Ugg lover or hater, I do have some reservations.

Growing up in Connecticut, it was understood that Uggs were like slippers or clogs. You wore them in the house in the winter, you threw them on after a long day of skiing or boarding, or you sported them to your brother’s November soccer tournament in Maine.

They were never high fashion; they were always functional. They were rarely worn in public, and definitely not when you were trying to look good.

So it baffles me to see young ladies today in short skirts and Uggs. The same goes for any other stylized outfit: this is the way I don’t like to see Uggs. It strikes me as poser-ish. Maybe it was acceptable that first season when Oprah declared it so, but to attempt to wear Uggs trendily now is absurd.

Here is where I am forgiving: if you truly love the Ugg boot. If you fell in love with Uggs during their hey-day, or before, or after, the fact that it is no longer “cool” shouldn’t stop you from wearing them. I know as well as anyone that you would be hard-pressed to match the feeling of real sheep’s wool on a cold day.

Please just note:

• Your Uggs don’t carry your outfit. Work them in creatively: Jennifer Supplee, who I profiled in September, wears unique textured or lacy tights and her tall Uggs with casual dresses and always looks great.
• Don’t wear them every day. Or often at all really. Again, this is a poser alert. Wear them every now and then, and wear them pretty casually.
• Don’t show off the boot. When I dress down, I’ll often leave my Uggs inside my pants–no tucking necessary. I am wearing them for comfort, warmth, etc., not to show off a label. If you’re not taking a new and unique spin on Uggs, sometimes its just as well to leave them hidden. They’ll still keep you toasty, but you’ll look unpretentious.
• Depart from Sand and Chestnut. If you step outside the two most common Ugg colors, you are bound to look a little quirky and different.
• Keep it simple. If you decide to go with “Fuggs,” beware of overdoing it. Boots with straps are cute. Boots with wool are cute. Boots covered in straps and wool and flower appliques and ten other things are too much. I find that Ugg brand boots are always in good taste. The patchwork boot, the text boot, last year’s purple boot with a subtle flower stitched up the inside–even if these are a little busy, they stick to a precise color scheme and a relatively simple design.

Unless you have a really creative take on the boots, when you wear Uggs you just want to make sure you don’t look like you are trying too hard. By keeping it casual you are sending the message that you equate Uggs with comfy pants or casual jeans and a sweatshirt. How very authentic of you 🙂