I know wearing denim on denim is basically the BIGGEST fashion faux pas, but I’m hoping you can help me! How can I style a denim shirt (or jacket) and jeans without looking like a ’90s mom? —Ella

Wait, Ella, are you insulting the beautiful double denim romance of Justin and Britney at the 2001 American Movie Awards?!

LOOK AT THEM ANGELS! Photo via Jeffrey Mayer/WIreImage.

LOOK AT THEM ANGELS! Photo via Jeffrey Mayer/WireImage.

My dream is to someday convince my boyfriend to wear this denim combo with me…even if it’s just to the Del Taco drive-through.

Girl, there’s no such thing as a faux pas! Wear whatever your heart desires, even if it’s a head-to-toe denim ball gown like Britney’s. It may not be for the faint of heart, but you can make it look amazing! I know I have before…or at least someone didn’t have the heart to tell me I didn’t. ::cryface::

The other day, during my monthly pizza club, one of my friends wore black jeans with a black denim jacket and I went bananas. He looked SO CUTE. It was like a goth denim tuxedo! I stared for a minute to try to figure out its magic, and I noticed that the wash on his jacket was slightly lighter than the one on his jeans. This subtle two-tone look really worked with black denim and can definitely also work for blue. Try wearing a light chambray denim button-up top with a darker denim on the bottom. Dark denim always looks classic and chic. Also, if you want to lessen the drama (though why would you?!), try wearing a boldly printed top under the jacket, which will draw attention away from your double-denim suit.

Go for it, you denim demon! Here’s some more inspiration, as if Justin and Britney weren’t enough on their own:

Clockwise from top left: Anjelica from Mode Junkie, Alexa Chung and Pixie Geldof, Tanesha of Girl With Curves, Debbie Harry; Rihanna; Nadia Aboulhosn.

Clockwise from top left: Anjelica from Mode Junkie, Alexa Chung and Pixie Geldof; Tanesha of Girl With Curves, Debbie Harry, Rihanna, Nadia Aboulhosn.

I have big calves, so the tall boots that strike my fancy when I’m shopping usually don’t fit me. They always get stuck right when I pull them up to my calf and then refuse to budge from there. Is there a brand of boots that will fit my legs? —Sydney

When I was in drill team in high school, we had to wear knee-high white go-go boots with our uniform. I’ve always had thick legs, and sometimes it would take two other girls from my team to help zip up my boots! My one friend used to joke that I needed a corset for my calves. THAT MUTHA.

This is something that I still struggle with from time to time, but nowadays, there are many shoes on the market that are made for thick legs. Old Navy makes some cool wide-calf boots, as does Torrid—I can personally vouch for the latter, since I bought a pair of gray suede boots that I absolutely loved! You can also search specifically for wide-calf boots online at Zappos, DSW, and Macy’s.

Another option: If you buy genuine leather boots, you can take them to a cobbler to have them stretched—but only if they’re REAL leather. Man-made materials usually won’t stretch and can be damaged if forced. If you’d rather just get ones that are already made for wide calves, here are some of my favorites:

Clockwise from top left: Slouchy Suede Heeled Boots, Torrid, $69.50; Romantic Soles Arva Boots, Zappos, $70; Style&co. Derby Wide Calf Boots, Macy's, $69; BCBGeneration Malino Wide Calf Boots, Macy's, $70; Lumiani Internation Collection Boots, Zappos, $118; Strappy Wedge Boots, Torrid, $69.50.

Clockwise from top left: Slouchy Suede Heeled Boots, $69.50, Torrid; Romantic Soles Arva Boots, Zappos, $70; Style&co. Derby Wide Calf Boots, $69, Macy’s; BCBGeneration Malino Wide Calf Boots, $70, Macy’s; Lumiani Internation Collection Boots, $118, Zappos; Strappy Wedge Boots, $69.50, Torrid.