About this time of year, I go crazy over boots. Whether they are sassy, sophisticated, provocative or simply warm, there is a style for every woman or you could say, every mood. The streets of San Francisco are replete with awesome boot muses. Here are a few I have delighted these days in spotting.

Part One: Booties!

It’s cold and/or rainy out, and your tootsies are a little too cold for regular shoes – much less sandals! – but you don’t quite feel like committing to a full boot? The booties below are worth noticing. They can be oh-so-stylish paired with skinny jeans, rolled up or tucked in as well as with skirts, bare legged or with tights.

How to wear booties

Beige stacked heel booties (pictured above) work so well with tucked in super-skinny jeans on super slender legs! In this case, breaking up the vertical line with a light colored booty actually works. (Can’t believe I am advocating for breaking up the silhouette!)

Notice how the oversized sweater emphasizes the twiggy-ness of the legs? I also like the way the booties echo a color in the sweater.

Check out the following three photos featuring booties with rolled up skinny jeans. It is so alluring to reveal in seasons of extra cloaking, just a tad bit of flesh at the ankle, don’t you agree? 

How to wear booties
Both these women look adorable, in my opinion, but I especially like the look on the right, with a slight bit of exposed ankle.
How to wear booties
Here is a smart, cosmopolitan answer to casual dress: infinity scarf, plaid (verrrry San Francisco!) button down top, rolled up skinny jeans and black booties.
How to wear booties
Even rolling up the jeans a few more inches works. Although I am seeing a lot of oversized tops/sweaters with skinny jeans, I find the fitted top more flattering.

If it weren’t for the apparent level of fitness of the muse pictured below, it would certainly be a challenge to pull off this skinny pant outfit in such a light color – not to mention, with booties of a low heel and wide toe box (with the potential of widening the figure visually). As in the case of ballerinas in white tights, the light color accentuates the form.

Although this lovely lady has the legs for ivory (read: visually enlarging) pants, the fact that her booties and sweater are of the same tone does help somewhat to elongate the silhouette. I also love the mix of neutrals with a classic blue denim jacket.

How to wear booties
With the wide toe box and sturdy lower heel, these boots are made for walking.

I must say I am thoroughly inspired by the way our muses above sport booties, but I am more partial to combining them with short hemmed dresses and skirts. It is the ultimate in wintry sexiness.

How to wear booties

The outfit pictured above is wonderfully unique in the way that the sienna colored booty (or boot-inspired shoe) contrasts with the navy/black jacket, navy blue dress and navy stockings. It makes for a lovely long vertical line with a refreshing pop at the feet.

How to wear booties

The two muses above stylishly pair booties with short dresses. The one to the left with a shorter hem is wise to wear tights with hers; not only is it a warmer outfit, but it creates a look of longer legs. The muse on the right appears quite chic in an all black ensemble broken up by exposed legs.

How to wear booties

Next we see a second pair of muses wearing more casual, sassy ensembles with booties. The muse on the right dons a pair of smart black shorts with a beige sweater, bare legs and sienna colored booties. For colder temperatures, the same shorts would be perfect with thick (cashmere!) tights and black booties.

The look of the woman on the left shows marked grunge influences, with the plaid shirt (in her hand) to be thrown on over the little black day dress and feminized work boots. Red socks peeking out over the top of the booties cleverly add a refreshing burst of color to an otherwise dark ensemble.

How to wear booties

The next look (above) is smart, chic and office worthy (especially with the length of the skirt). It is so simple and clean, with the jacket matching the booties and a bright “shot” of blue in the skirt. The close-to-flesh-tone of the booties keep them from breaking up the line of the leg.

Wearing booties with a dress
Love love love this 3/4 length kimono sleeved dress of lively black and white print with dramatic red panel.

Our last muse demonstrates perhaps my favorite look and the greatest challenge here: pairing booties with a dressy dress. It certainly doesn’t hurt that the booties have an ultra high heel and are wickedly elegant, with a pointy toe and close fit at the ankle. Together with opaque black hosiery, they do a beautiful job of lengthening the leg.

The leg- and footwear are so sleek and subtle that while being on par with the elegance of this amazing dress, they do not compete with it.

I hope the looks above have inspired you and sparked new ideas as they have for me. While I love the look of bare legs with similarly colored (beige) booties, temperatures have turned a bit nippy for me to go there. But I am moved to start wear my booties more often with short skirts/dresses and tights when I’m in a flirty mood – or rolled up skinny pants when I’m feeling more like a tomboy.

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