Hilery Sirpis has a case of the blues. The 40-year-old Alexandria mother of two, an advertising director for Government Executive Media Group, owns about 50 pairs of jeans.

How did the denim obsession start?

In college at Louisiana State University, I remember wearing men’s Levi’s and getting them tapered. Back then I maybe owned five pairs, and I lived in them. In 2001, I bought my first “premium” denim—Citizens of Humanity jeans from Neiman Marcus. I still wear them—they’re my soccer-mom jeans.

Your favorite pair?

I have a great pair of traditional Hudson jeans. They’ve got a perfect pocket and just the right amount of detailing. I don’t like whiskering or fancy jewels.

What’s the most you’ve paid?

I purchased my Habituals at a boutique in Louisiana and paid close to $200.

Anywhere you won’t wear jeans?

You can wear them everywhere, except maybe to dinner at Citronelle. I can’t wear them to work except on Fridays.

Where do you shop?

I love the Georgetown Barneys Co-Op, Denim Bar, T.J.Maxx’s Runway section, and Filene’s Basement. And Loehmann’s, the one on Route 50 in Falls Church—they’ve got a great selection.

What shoes do you pair with jeans?

I love to tuck jeans into boots—flat for day, heels for night. I pair jeans with peep-toe pumps in winter and flip-flops in summer. Sneakers are a no-go. After a pair has lost its going-out appeal, I’ll have them cut off to wear with flats. I don’t bother to have original hems resewn; my jeans always drag and get ragged at the cuffs anyway.

Have you always loved shopping?

For me, shopping is like my husband’s love of golf—it’s fun and relaxing and a challenge. You could go to Neiman Marcus and pick out a great outfit, but that’s no fun. It’s the hunt—pairing one expensive piece with add-ons from H&M, Urban Outfitters, or T.J.Maxx. Toutie.com is one of my favorite Web sites, and I’m obsessed with Gilt Groupe.

This article is from the February 2009 issue of The Washingtonian. For more articles from the issue, click here.