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Q. Help! I just moved to a cold climate and can no longer wear ballet flats with my boyfriend jeans. I have seen celebs, such as Rachel Bilson, wear boots with boyfriends and it looks good.. How do you do this? Do they have to have a heel? I would prefer a low heel or flat. Also, can you recommend any that are less than $150?

A. It can be somewhat tricky to pull off a boyfriend jean with boots, but it definitely can be done. An ankle boot with a heel is the easiest style to wear, however, a flat combat-style or rugged boot also looks great (see Jennifer Aniston, below). If your cuffs hit above the top of your ankle boot, add some wooly socks for warmth (and style).


D&G Spring 2010 runway; Marni/Current Elliott Spring 2010, Ralph Lauren, Jennifer Aniston (via x17online)

Here are some boots under $150 to try with your boyfriend jeans.

Q. I’m a 5’2” girl with a medium frame weighing 120 lbs. I have a pair of black boots with heels that are knee high. Those boots are great, but I can’t wear heels all the time. I want a cute pair of boots that are flat but also flattering to my figure. What do you suggest?

A. Petite women can absolutely wear flat boots, it’s all in the proportion. While you may be able to pull off a knee high boot with a heel, a flat knee high boot might not be as flattering. Instead of knee high, look for boots that hit a few inches below your knee (around 12” tall) for the most flattering look. Another option is to choose an ankle or mid-calf boot that you can still wear with leggings or skinny jeans. Here are some flat boot options to try:

Q. A very generous friend gifted me a pair of leopard Louboutin pumps. They are Beeeautiful. I’m wondering what to wear them with so as not to overdo the look. I’m assuming a pair of skinny black trousers, but what kind of top? I have a nephew’s engagement party at a restaurant coming up and thought this would be the perfect opportunity.


A. Now that’s a friend! Can you make an introduction? Kidding aside, congrats on being the proud owner of a new pair of leopard Louboutin pumps. It is no secret that I have a serious love for leopard print shoes, so you’ve come to the right place.

There’s a reason I love leopard pumps: they’re eternally chic and can be worn with almost everything. A few examples: jeans and a blazer, skinny black pants and a tunic, a pencil skirt and blouse, camel trousers and a sweater, a little black dress…see what I mean? Everything. Day or night, work or weekend, dressy or casual, leopard pumps do it all.

Some favorite colors to pair with leopard are red, black, brown, camel, orange, blue, gold, yellow, pink, green, mustard and charcoal grey. Leopard shoes can even be paired with prints, but this is where it can get a little tricky, so if you’re not comfortable mixing your prints, then stick with solid colors. Take a look at two of Heidi Klum’s recent looks for great ways to wear leopard pumps with prints.

For those of you reading this who don’t already own a pair of leopard print shoes, it’s time to add this key piece to your wardrobe now — and you don’t have to spend Louboutin prices. Here are some options to get you started:

Q. I think I have found the perfect transitional boot for the fall season. It is the Naya Genesis in the Graphite Suede. My question is, can I wear theses beyond the fall season? They have a peep toe and I live in Minnesota. Can I wear tights with them or socks in the winter? I’m in my forties. I love these boots, but I feel they may not be worth it if I can only wear them for the short fall season.

A. Do you want the good news or the bad news first?

Good news: Yes! You can absolutely wear open toe booties with tights - just be sure there is no seam at the toe, or that the seam is safely tucked away and not visible.

Bad news: I’m afraid that there isn’t a tight made that is warm enough to keep your toes from freezing in the middle of winter in Minnesota. Unless you are going straight from a heated car to heated indoors, it’s best to stick with a closed toe style in the winter.

Only you can decide whether you will wear these booties enough to make the investment worthwhile. However, you’ll be happy to know that you can wear these through the fall until the cold weather hits, and then again in the spring until you’re ready for sandal season. Though once quite trendy, the open toe bootie has been with us for several seasons now, so you’ll likely be able to wear them at least through fall 2012 again, if not longer.

Q. I have seen some ladies wear rain boots as winter boots. Is this okay? I bought some fabulous black Michael Kors rain boots and I bet if I put warm socks on underneath they would be warm enough to double as winter boots here in Washington, D.C. It would be great to get some extra mileage out of them.

A. Yes! Actually, I often wear my rubber rain boots in the winter, especially since they are a tiny bit big on me, so there’s plenty of room for thick socks. Even better, there are rain boot liners or Welly Socks available that are made specifically for the purpose of wearing with your rubber Welly-style rain boots in cooler weather. They come in a variety of fabrications including fleece, faux fur, and cable knit wool in everything from simple colors to wild animal prints. Here are a few to consider:


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