5 essential looks from underrated style icon Lisa Loeb

June 11, 2014

We revere certain artists for their style, and the sooner that we accept that, the sooner we’ll be able to admit to ourselves that we dressed how we did because we wanted to be so-and-so from such-and-such.

In contrast to the likes of Courtney Love, Missy Elliott, or even Victoria Beckham, there were the musicians who brought unique aesthetics to the table and were overlooked in the process. Maybe we cited them as “safe,” or maybe we thought they were too much like we were (they weren’t), but either way, we bypassed them completely, and are only now realizing the impact they had.

So in celebration of the artists who dared be themselves, here’s a choice for who we deem an underrated style icon: Lisa Loeb—the woman who made our middle-school glasses seem a little less ostracizing—and our five favourite/most important looks.

1. Those Glasses

Well, let’s just cut to the chase: Lisa Loeb is synonymous with glasses. Cool glasses. Vintage glasses. Glasses that command respect. Glasses that say, “I am here, and I am allowing you to see, and I am improving your overall aesthetic in the meantime — you’re welcome.” Thanks to “Stay,” Ms. Loeb established just how big of an impact glasses could have (and also worked to humiliate anyone who’s ever made a dig at and/or about glasses). She is their patron saint.

However, on that note, you can take your “sexy librarian” jokes and shove them up your . . . mid-90s nostalgia post.

2. Animal print

It’s not the mid-to-late ’90s without animal print, and if you have any doubts, introduce yourself to Peggy Bundy’s Married With Children wardrobe. However, as opposed to the spandex leotard/button-up combination, Loeb went the edgier route (yes, there is one) by pairing animal print faux fur with black leather and chiffon sleeves, which officially establishes the late 20th century power trifecta.

But she doesn’t take it too far: while the dress length (especially in the mid-’90s) would’ve been fine without tights, Loeb still went the opaque route, effectively giving us a tutorial in “how to walk the line between edgy and almost-work-appropriate.” (If your job was singing songs we define our emotions with.)

3. Black turtlenecks

Blunt bangs, black turtleneck, that’s the way we like to . . . describe the third most important look of Lisa Loeb, who embraced the traditional coffee house aesthetic with her monochromatic choices circa ’96. True, you can’t go wrong with black, but to carry off both a turtleneck and bangs is a feat to be celebrated. (Particularly if you, like some of us, don’t have much of a neck — though fortunately she does. Go Lisa!)

4. Tutus

Approximately .0004% of the population who don’t practice ballet can carry off tutus, and Lisa Loeb is one of them. But what’s  interesting is that despite the obvious girly-ness of, well, a pink crinoline skirt, Loeb doesn’t wear them conventionally: she mixes and matches her tutus with tube tops or even sweaters, further establishing herself as a woman who challenges style convention (and further establishing the ’90s as an era that championed eclecticism).

She also doesn’t infantilize. And you don’t have to be “girly” or “not girly,” you can just . . . wear a tutu. No one has to be a sexy baby at all.

5. Dresses, every day, all the time

Hands up if you’ve seen a photo of Lisa Loeb wearing pants. Okay, well . . . hands down, show-offs. The important thing is that for 20 solid years (at least), Lisa Loeb has established herself as a bona fide dress connoisseur. From her baby doll number in “Stay” to the plaid jumper you see above, to the red lace tea dress she wore on John Oliver recently, the singer-songwriter knows what style works for her. But on the flip side, she doesn’t play it  safe: she experiments with patterns, textures, colours, lengths and necklines. Dresses may be her “thing,” but a specific type of dress is not.

Lisa Loeb’s look is far more than a specific piece, or a certain hemline — much like her songs. There’s a reason we still care about her music, and why her career’s spanned decades: there’s depth to it, and there’s heart. Loeb arguably puts the same thought into her wardrobe, too. She’s not dictated by what she wears or by trends, but she chooses her pieces carefully; she wears what works, and damn it, she’s the first person who comes to mind when justifying the purchase of any more baby doll dresses. So Lisa Loeb, if you can read this, teach me how to wear a black turtleneck.

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