Dear Answer Angel: As the temperatures drop, I feel the need to cover my head. The problem is, I don't like how I look in hats. I have never found a warm winter hat that looks attractive on me. Do you have any suggestions?
Dear Answer Angel: What about the problem of wearing hats in the winter and then having hat hair. Can you suggest hats that are both warm and stylish?
— Debbie S.
Dear Hat People: In general, warm hats are ugly and cute hats don't do the job. Meanwhile, unless you've got movie star hair that is luscious and indestructible, hats mash your hair so badly that you look like you've been wearing a pillowcase on your head.
There are no ideal solutions but here are a couple suggestions: Earmuffs have come a long way and you now can buy them to go over your head, behind your neck or as two little fuzzy discs that just cover the ears and aren't attached to each other. There also are wired ones to plug into your iPod. An online search will leave you dazzled with the options. However, you've only solved the ear problem and your head is still freezing and open to the elements.
Then there's the knit headband option with the same top-of-head freezing problem. Any warm hat that covers everything is going to wreck your hair. And don't even think about a coat with a hood. Those things never stay on your head when you need them most — in a blinding snow storm, for instance.
Berets, especially ample knit or felt ones you can pull down over your ears, do less hair damage than most but they can look frumpy.
Bottom line: If you want to be warm, you're going to be a fashion/hair don't. You know what? When it's 10 below, how we look is truly the least of our problems.
Dear Angel: You have wings so you never have to worry about slipping and sliding and sloshing in ice and grimy snow on city sidewalks. But for us humans, two questions: First, when I arrive for a dinner party at a friend's home, should I take off my boots and change to shoes at the door so I won't leave messy footprints on the carpet? Wiping snowy boots on a door mat usually doesn't leave them clean and dry. Second, if I'm heading to a good restaurant in a pair of dressy pants, will it look terrible to tuck them into thick-soled boots?
Dear L.W.: More and more people have adopted the Japanese custom of leaving shoes at the door. So, before you leave your house, make sure your socks don't have holes!
Back to your first question: Always ask your hosts if they'd like you to change to street shoes when you arrive. Most will appreciate that you're not tracking that gunk across their just-vacuumed carpeting. And you're right, wiping your boots on the door mat is not a solution.
As for the restaurant issue, dressy pants jammed into winter boots is a fact of life. No, it's not a great look but it's inevitable. You've got two options: Change into street shoes at the coat check or forget it. I recommend the latter. Once you're seated, nobody's going to look at your feet anyhow. And everyone else is wearing salt-stained boots too. Yes, there are waterproof boots that look decent but not many Check out the pricey La Canadienne brand, lacanadienneshoes.com.
Dear Answer Angel: I treasure my cashmere sweaters but don't know how to clean them. Do I send them to the dry cleaners or hand wash them? And if washing is the answer, what detergent do I use?
— Cleaning quandary
Dear Ms. Quandary: Stop right there and back away from the detergent! I stopped by Manrico Cashmere on the Magnificent Mile — 970 N. Michigan Ave.— to get the 411 on how to best answer your question at a store that sells nothing but cashmere. They ought to know! There I learned that you should never dry clean and never, ever use detergent. Not even Woolite. To retain maximum softness (which is, after all, the whole point of wearing cashmere), wash by hand in cool water with baby shampoo. Who knew? Don't wring. Lay flat, gently pressing out moisture. Let dry. Luxuriate.
Dear Answer Angel: I'm going to a party in downtown Chicago. It's going to be cold. Can I wear sheer hose with peep toe shoes or do I need to wear pumps?
Dear Heidi: I don't like to see stockings, even though sheer, popping out of the toe. They're called peep toes not peep hose after all. I think that this style of shoe works best without hosiery — not exactly a good call in Chicago in winter. So, wear pumps. Unless it's wet. In that case, wear boots and change once you get there, especially if your dressy shoes are expensive or favorites They will never fully recover if they're sloshed in slush.
Dear Answer Angel: My teenage daughter and her friends are totally into vintage, especially old costume jewelry. Any shopping suggestions?
— Trying to help
Dear Trying: Boy have you come to the right place. As the proud owner of 500 plus pairs of (cheap!) vintage earrings, I know an awful lot about this. My advice is to hop in your car this minute and head to the best vintage jewelry shop around here. It's Antique Jewelry & Resale, in a strip mall at 7214 N. Harlem Ave. (at Touhy Ave.), antiqueandresale.com. This will not be a quick pop-in. Allow at least two hours for browsing. Seriously. Owners Jules Breen and Suzanne Lazer keep adding stock and the prices are amazingly reasonable. And be sure to check out Breen's window displays. The current one, "Lip Smackin' Sweet Christmas" on a candy theme is awesome. Also worth a look is the just-opened Oak Park Vintage Market, 1117 Chicago Ave., Oak Park, oakparkvillagemarket.com.One more thing, if you're visiting the seashore in Maryland or Delaware, Dave Mayer's Millsboro Bazaar in a former funeral home on Main St.in Millsboro, Del. is a must stop for vintage jewelry lovers.
Dear Answer Angel: I recently purchased a gorgeous vintage blue leather purse at the Randolph Street Market. It's in pretty good shape except for abraded corners and a little stiffness in the strap. Do you know of anyone who can restore a purse? I've heard these services exist but don't want to take it to any old shoemaker unless I know they just won't coat it with shoe polish. I didn't pay that much ($45) but am willing to spend some more.
— Danielle L. S.
Dear Danielle: A picky vintage purse fanatic friend was delighted with work done by Without a Trace, withoutatrace.com which has two Chicago locations: 100 E. Walton St. and 3344 W. Bryn Mawr Ave.
Shop, drop, get help: You have problems? Don't we all. But here's the difference. You've got an angel (with attitude) on your shoulder. Send your questions — on style, shopping, beauty and makeup, to firstname.lastname@example.org.