Trend: Convertible Boots

Solid winter boots are an investment to say the least and once you find a reliable pair, that's all you want to wear. In my case, this usually means wearing L.L. Bean boots with jeans, skirts and dresses. That is why I am smitten with the idea of convertible boots that go from ankle to knee-high. These options from Ugg Collection and MM6 Maison Martin Margiela are perfect examples of two-for-one. I would wear the shearling-lined Uggs trampling through the snow and the high-heeled Margielas to work.

Uggs originally seen on Honestly...WTF

Need: Tartan Pants

Last year I saw the perfect pair of tartan motorcycle pants and though, there's no way these will last in my closet. Sure enough, a year later they remain one of my big shopping regrets. The good news is that there are a ton of options to fill that void from McQ to Rugby to Etoile Isabel Marant. Now the only question is when they go on sale.

Fall Shopping Vol. 2

Although it could probably be said of every season, I think there is a strong case for the return of more feminine shapes this fall. Me and my curves couldn't be happier. From the moment I spotted this Donna Karan leather jacket, I knew it was the perfect way to cover up come fall. The nipped waist and patch pockets give the delightfully '80s utilitarian look some sex appeal. I imagine wearing it to work as a ladylike twist on Sean Young in "Blade Runner," trade robot love for Twitter addiction.

Donna Karan Belted Leather Jacket
Rugby Ralph Lauren Donegal Tweed Skirt
ManiaMania Third Mind Cuff
Pour la Victoire Daina Pump

Fall Shopping Vol. 1

For fall, I'm all about the subtle asymmetry of this Ann Taylor skirt. I can see dressing it up for the office and down for a weekend look. A chunky sweater and sleek booties sort of make it work for both occasions. I find this look so flattering and versatile, for $88 I'd even go into an Ann Taylor.

Ann Taylor Asymmetrical Ponte Skirt, $88, at AnnTaylor.com
Thakoon Addition Asymmetrical Chunky-Knit Oversized Sweater, $460, at Shopbop.com
Maison Martin Margiela Set of 4 22-Karat Gold-Plated Knuckleduster Ring, $480, at Net-a-Porter.com
Stuart Weitzman Held Bootie, $425, at Zappos.com

Full disclosure: I walk past both Stuart Weitzman and Ann Taylor on my way to lunch most days. I have to think it's starting to affect me.