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Q. What type of socks should you wear with the new Mary Jane type chunky shoes? Please specify what type with jeans and with a skirt.

A. The great thing about the new Mary Jane and chunky T-Straps is that anything goes when it comes to hosiery. Whether you are wearing them with jeans, wide leg trousers, skirts or dresses, you have many options available to you:


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 and the rest are from

raroy2005110700_prod_medium_v1_m56577569831206739.jpg br607772-00vliv01.jpg br606572-01vliv01.jpg br588150-01vliv01.jpg br-otf-out12419odv01.jpg
Lanvin-knee-boot.gifQ. First, I love your site, especially the Ask Us feature. So naturally, I thought I’d send this question to StyleBakery! I would love a pair of the Lanvin Flat Knee-High Boots, but at a more affordable price. I’d still like something quality that will last, but not priced at $1000! Any idea where I can find the same look?

A. Great boots, but scary price tag! The good news is, we found some amazing flat boots in a range of prices, all for less than the Lanvins. Scroll through these options:

Q. Is it just me, or is finding a pair of flats with arch support like searching for the Holy Grail? I have flat feet and stand all day long for work, so I need something supportive that’s not a sneaker … but also fabulous and stylish. Unfortunately, it seems like all the shoes I’ve tried in stores and online have thin soles and little or no cushioning. (The few that do fit the bill comfort-wise look bulky or geriatric.) I’d love to find something work-appropriate in a cranberry and/or metallic, but at this point, I’m not picky about color! (On the technical side, is there any reason why designers *can’t* add cushioning or support to their flat or low-heeled shoes? Seriously — I’m curious.)

A. It may seem like an impossibility, but fashion and comfort are not always mutually exclusive when it comes to shoes. More designers these days are making foot-friendly and fabulous footwear. Cole Haan’s line of Nike Air® cushioned shoes is one of our favorites, and Aerosoles is known to have some stylish offerings on occasion.

Here are several ultra-comfortable flats that you can wear to work:

Cole Haan ‘Air Sierra’ Flat
Cleverly concealed Nike Air® cushions the foot for long-lasting comfort.
$185 at
Cole Haan ‘Air Camille’ Flat
Padded footbed is coupled with concealed Nike Air® cushioning for maximum comfort.
$195 at
‘Trina’ from Walking Cradles
Padded footbed with massaging bumps offers soothing support.
$83 at
SORBET_PD.JPGAerosoles Sorbet
Extra cushioned footbed gives day-long comfort.
$69 at

6627-600491-d.jpgMagnolia by Lumiani
Fully cushioned footbed.
$130 at
Gentle Souls Bay leaf
Flaxseed pillows conform to medial and lateral arch.
$195 at
‘Wassilla’ flat from Vaneli
Cushioned footbed creates slipper-like comfort.
$106 at
pl592664-00vliv01.jpgClarks Adore Yours
Cushioned footbed and crepe outsole.
$105 at

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