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Q. I am desperately looking for shoes to wear when it’s raining. I already have a pair of rubber Wellies but want something with a bit more style. Any suggestions?

A. We found a slew of chic waterproof shoes - many of them you’ll want to wear rain or shine. Scroll through our picks below:

Q. Ankle Boots are everywhere this Fall. I’m happy about this, since my calves are too dense for mid-shaft boots, but more importantly because I live in Florida, where Autumn is a stylish state of mind, and not much else. I have no idea how to actually WEAR the ubiquitous ankle boot. I know they can be paired with trousers to give the effect of wearing a full on boot—but what else? How do I pair an ankle boot with skirts or dresses? Most importantly: how does someone who isn’t 5’10” and 115 lbs wear an ankle boot without making their legs look shorter/wider?

A. True, ankle boots, or booties, are everywhere this fall, worn with everything from skinny jeans to dresses and skirts. This doesn’t mean it’s a trend for everyone, however. Those with shapely calves may have a hard time wearing ankle boots with a skirt or dress since the boots tend to make even thin calves look a little thicker. If you’re petite or have short legs, be aware that booties will chop inches off the length of your leg, though this can be compensated for with a high heel.

If you think you’re ready to give ankle boots a try, here are some chic options:

1. Wear your ankle boots with skinny jeans
2. Wear them with dresses or skirts that hit just above the knee or higher, below the knee is harder to pull off. You can wear this look bare-legged or with opaque tights.

Here are a few visuals, on the left is from shopbop.com and the rest are from bananarepublic.com:

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Q. I have a lovely red satin dress that I would like to wear to a wedding but I am a little worried because everything I read says not to wear a red dress to a wedding…is this still true? Or is it an outdated taboo? I plan on wearing silver strappy shoes…but I am not sure how to do my makeup?

A. There are many who believe that wearing black (too funereal) or wearing red (too attention grabbing) to a wedding are big faux pas. I, however, am not one of them. To me, a little black dress is eternally chic, whether worn to a wedding or any other affair. As for red, in most cases it should be fine, provided it’s not too lowcut or too sexy. The idea is not to steal the attention from the bride, so a super sexy and revealing dress in red (or any other bright color for that matter) is not appropriate. If your dress, accessories and behavior are tasteful, there should be no issue with the color of the dress.

To address the second part of your question: yes to silver strappy heels. Your makeup and hair should be simple and sophisticated in colors that work for your complexion.

Here are three gorgeous red dresses to wear to a wedding or other dressy affair:

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Lauren by Ralph Lauren Cutaway Crepe Dress

$152 at nordstrom.com

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Anne Klein Dress Stretch Satin Sheath Dress

$178 at nordstrom.com

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Maggy London Beaded Silk Chiffon Dress

$158 at nordstrom.com

Q. I’m looking for a designer, rather large/roomy tote to carry around for school. The hard part is that I really want a zipper wall that goes down the middle inside the bag so my books/binders can stand upright and not fall over and also to separate my wallet/makeup-bag from my books. I have searched furiously online with barely any luck. My price range is up to $450 I would say. Any suggestions!?

A. This proved to be tougher than we thought! Here are three chic options that contain the center zip compartment you’re looking for. And if any of our readers have other suggestions, we’d love to hear from you in the comments section below!

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LeSportsac Lexie Tech Tote

$120 at shopbop.com

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Hayden-Harnett Catalina Slouchy Laptop Brief

$473 at haydenharnett.com

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Lodis Accessories Milano Tote With Laptop Pocket

$279 at zappos.com


Q. I have a red leather biker jacket. Can I wear it this season?

0900631b81524006M.jpgA. Motorcycle jackets are huge this season. Though we’re mostly seeing them in black, brown or gray, your red version should be right in step with the trend. We found a red Helmut Lang moto jacket at barney.com for a mere $1,290 and a red faux leather jacket at jcpenney.com for $39.99. In addition to jeans, try wearing your jacket with feminine skirts and jackets for the look of the moment.

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