Joan Rivers

Charles William Bush

Dear Joan:
I am so glad you are back on E! and talking fashion. How should a man or woman in their thirties dress to go to a club without looking trashy? What role models should we follow? Please advise!

Dear Perplexed in the Big City:

Me, too, thank you! George Clooney or Matt Damon always look classy. And I've never seen a nipple slip from Jennifer Aniston. Basically, don't look to the Jersey Shore for inspiration. GTL is not a formula for fashion success.

Dear Joan:
My mother is 62, petite, cute and is in great shape. She jogs every day. My question: Any tips on a fashionable ensemble for jogging for an older woman? Although she might be able to pull it off, a sports bra and tight booty shorts isn't the look I was going for. My mother and I love your show! I was skeptical about Kelly Osbourne, but she has proven to be a great addition and I love her style!

Dear Family Man:
Good for your mother! And you, too, for being such a thoughtful son. We should all be so lucky. I'm not gonna discourage the sports bra—at her age she needs all the support she can get—but she should be topping that bra with a T-shirt along with some stylish running pants and a matching jacket. And you're right on about Kelly, she's quite the fashionista!

Dear Joan:
My mum and I are going for a winter vacation and it's always summer in my country (Malaysia), so I was wondering if you could help me dress. Help! I need to look stylish even though I'm gonna be freezing!

Dear Snow Bunny:
Don't worry, you're going to be fine. Dressing for winter gives you so many more options to be stylish—there's a coat, boots, scarf, hat, etc. And then there are all the layers you get to play with, like a sexy cami beneath a nice blouse with a gorgeous jacket. Bon voyage!

Dear Joan:
I mostly own T-shirts and a few nice shirts. How can I dress up my T-shirt to make it more fabulous?

Dear Shopaholic:
You're in luck: layering casual items with nicer pieces is the thing to do right now. So take a page from Kelly, who's been looking great lately in all her fitted blazers. Nothing dresses up a T-shirt like a nice jacket and some good pants or even nice jeans.

Dear Joan:
I am a big fan of your show. I'm wondering, how do I look good and still be comfortable?—Basketball_10chick

Dear Sporty Spice:
The right fit and good quality fabric will go a long way toward making you feel comfortable in nicer clothes. It just takes a little extra planning to put together an outfit that makes you look great—start the night before by laying out your clothes for the next day, and don't forget accessories!

Dear Joan:
I'm going to my friend's 14th birthday party, but I don't know what to wear. I can't choose between a nice minidress or casual jeans and a shirt.
—Marwa Silva

Dear Party Girl:
You're going to have fun no matter what you wear, but it's important to consider your surroundings. If she's having pizzas delivered, go with jeans and a shirt. If the party is out somewhere, like at a restaurant, then the mini is your best bet.

Dear Joan:
Love you! OK, I know prints, patterns, lines, etc. are in, but I'm like Beyoncé when Hollywood says she is fat! Can I still wear it and not look like a drum?

Dear Stripes:
Thank you, my dear! Of course you can. Anyone who calls Beyoncé fat is crazy. Period. So wear what you want and be happy. Life is too short to worry about what Hollywood or the haters think.

Dear Joan:
I am a fortysomething who has recently become disabled. What type of blouses look the best while sitting for a boobalicious woman?

Dear Chesty:
I'm sorry to hear that, but you sound like a fighter! Fitted clothes always flatter a big chest (lucky you!) better than loose and blousy. Just make sure that there's no pulling if your top has buttons across the chest area. A nice rack is great, but there's no point putting on a show for free.

Dear Joan:
I just bought these red heels. I don't know how to put an outfit together to wear them with. Do you have any suggestions?

Dear Dorothy:
Red is such a great pop of color with all the neutrals this fall. Your shoes should pair nicely with a black pantsuit, a camel skirt or even a pair of jeans. Now go click your heels!

Dear Joan:
I am 54 and would love to wear headbands. Am I too old? I don't want to look like I'm trying to be on Gossip Girl.

Dear Upper East Side Mom:
Remember Jackie O. or Grace Kelly? They were both MILFs who wore classic headbands all the time. Just leave the plastic or cutesy stuff to the Gossip Girl kids.

WATCH: Fashion Police Friday nights at 10:30 on E!
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