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Ellen Warren. (Zbigniew Bzdak/Chicago Tribune)
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We’ve all done it. Opted for cute instead of comfortable shoes–and paid the price.

Some of us vain types (I plead guilty) just don’t seem to learn from our mistakes. And the rest of us have learned too well, opting for comfort even when the result is some ugly footwear.

Styling myself as the Great Shoe Compromiser, I set out to find a foot-happy middle ground, to locate shoes that feel good and look good.

My first step was to learn more about the enemy, those shoes that are easy on the feet but hellish on the eye.

I didn’t have to look far. Two co-workers swear by their comfortable footwear, despite my continuing ridicule. I asked them to make the case for their faves. And then I weighed in with my 1-5 “ugly rating”–5 being the ugliest.

Defending their comfortable shoes: Lara Weber, an At Play editor; Monica Eng, At Play staff reporter.

Do you agree? Tell me at my blog, chicagotribune.com/ellen

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1. Keen Newport Sandal, $94.95, Nordstrom (nord strom.com), REI (rei.com); zappos.com and shoe retailers nationwide.

Ellen’s ugly rating: 5

Lara: What if flip-flops and hiking shoes mated? You’d end up with these. I like these rugged waterproof shoes for rain-soaked music festivals, where I can tromp through muddy fields.

Ellen replies: Just hideous. I guess they’re OK if you promise to wear them only in crowded, muddy fields.

2. Arizona sandal, $99.95, www.birkenstockusa.com; Hanig’s Birkenstock Shop, 847 W. Armitage Ave., 773-929-5568 and shoe departments nationwide.

Ellen’s ugly rating: 4.5

Lara: I, too, once resisted these. They start out a little stiff and then, like magic, transform into perfect pillows for your feet. OK, so they’re more backpacker chic than runway chic.

Ellen replies: No chic, no how. Please don’t tell me you wear them with gym socks. The only people who should wear these in public are those akin to my 84-year-old mother, who really couldn’t walk comfortably until she discovered Birkies. Sorry, Mom, they’re still nasty.

3. Dansko professional in oiled black, $114.95, The Walking Company, Woodfield Mall, Schaumburg, 847-995-8817 (walkingco.com), Nordstrom and stores and retailers nationwide.

Ellen’s ugly rating: 4

Monica: Along with a ton of attractive chefs and doctors, I wear these because they feel so great on my feet, especially with the ankle support at the back. Any dude or dudette who has a problem with that doesn’t need to be my (boy)friend anyway.

Ellen replies: Phew, glad I didn’t want to be your boyfriend, Monica. I will defend to the death your right to look like a ’70s retread.

4. Donald J. Pliner Shina, last year $200 at Nordstrom, 520 N. Michigan Ave., 312-379-4300, nordstrom.com; similar Agnes, $125 or Darsi, $140, on sale at donaldjpliner.com.

Ellen’s ugly rating: 3.5

Monica: I wear them with everything, they are so darn comfortable. The buttery leather has molded to my feet and gives them a worn but still work-appropriate appearance.

Ellen replies: These are the best looking of this parade of the putrid. But the obvious heel padding and inset in front give them that awful ortho look. I once ditched my gynecologist for wearing shoes that weren’t even this ugly.

Cute and comfy

Ellen makes the case for alternatives that are easy on the feet and the eye:

5. Cole Haan Tivona Air sling, $275, colehaan.com

Ellen: I was so convinced that these sexy slingbacks would be cripplers that I asked our fussy Birkie queen, Lara, to give them a whirl. Before the test, as the shoes kicked around the office, from my desk to hers, men wandered by and gawked approvingly. Trust me, they were not interested in the “state of the art high heel” that Cole Haan boasts of pioneering with Nike technology. But a crazy thing happened. She really liked them. Let her tell you …

Lara: They’re sturdy and comfortable–if you can manage a 4-inch heel. I tried walking 10 city blocks but ended up walking about five, then hailed a cab. Good cushioning and a nice flex in the sole.

6. Palladium Kassel flat, brown hair calf, $74.95, Nordstrom, nordstrom.com

Ellen: Love, love, love. A cute ballet flat vibe with an A+ comfort rating. And the hairy-animal look gives these a funky edge. The photo does not do them justice because they look a lot cuter on. I was so impressed with the look/comfort of these babies that I went online to zappos.com and bought another pair in black leather. Close to perfect.

7. Irregular Choice, $179, Bloomingdale’s, 900 N. Michigan Ave., 312-440-4460, bloomingdales.com

Ellen: This is a great option for those of us who can’t wear stilettos but still want some height. I’m no fan of the ’80s bootie but these would look primo with pants or jeans. The heel is conical and a fun twist on the more popular curvy kitten heel. Plus, there’s a tiny turn-up at the toe, a little elf and little sparkle, thanks to the sheen of the leather. If you’re over 20 and are wearing these with a skirt be warned: You’re a fashion don’t.

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TO BUY SHOES THAT LOOK AND FEEL GOOD

– Rubber soles are more forgiving and don’t have to be ugly, although they often are.

– Stores that specialize in comfortable shoes do not make cuteness a priority. Beware.

– Try them on at midday when feet are the biggest.

– If they hurt in the store, don’t buy them

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For an upcoming column, tell me what makes your craft fair special enough to be included in a listing in this space. Send details and a contact number to shopellen@tribune.com.

For more shopping, see Ellen’s “Just One Thing” column in the Tribune magazine on Sundays and join the conversation at chicagotribune.com/ellen