It’s been said that a girl can’t have too many pairs of black shoes, and boots fall easily into that category. Whether flat or heeled, sophisticated or casual or somewhere in between, in the winter you can’t go wrong with a great pair of black boots.

For a while, my favorites were the Frye Harness 12R style. But I’ve always longed for something a little more bad-ass and with a taller shaft, so the Frye Jenna Chain Tall boots caught my eye this fall.

On a random trip to Nordies, I tried on a pair and it was instant love. In short, I’ve been looking for these boots all my life. They fit perfectly, from the toes to the calf circumfrence. I’m 5’7″ and these boots hit exactly below the knee, with enough room for tights or jeans tucked in. The insoles have a bit of bounce, so they are comfortable in addition to looking amazing. The bits of chain add exactly the right amount of shine to an incredibly classy, quality boot. I can envision these with skinny jeans and a sweater tunic, or a sassy denim skirt and tights, or even a sweet flowered dress. The only mistake they made with these boots is naming them Jenna instead of Gemma.

If you order the Frye Jenna Chain Tall boots today from Zappos, you can have them at your front door tomorrow!

I’ve been looking at Hunter boots for a few years now. I almost bought some a couple of years ago, but at that time they only came in orange and the ubiquitous shade of bottle green. I saw a lot of them when I was in NYC back in March, because the weather was rainy and chilly, and they seemed to be a good mix of practicality and style.

My husband calls these “pretentious wellies”, partly because he is from the UK and the Queen used to wear Hunters when she was out in the fields with the hunting dogs. Also, at $125, they are pretty pricey as wellies go. However, the quality is excellent, the cut is chic, and now that they come in dozens of colors and the new Gloss finish, they are pretty hard to resist. Hunter has been in business since 1856, so they must be doing something right. I ended up ordering Glossy because the traditional matte rubber can turn chalky over time…and also because I like shiny things!

There’s been some discussion of Hunter sizing — some people say they run large, others say small. I normally wear a size 8 or 8.5 shoe, and the size 39 Hunters fit me perfectly with medium-weight socks. They are shaped like a riding boot, and fit my (average) calves exactly. If you will be wearing these in a cold climate, I highly recommend getting them large enough to fit heavy socks, because rubber boots are notoriously bad at retaining heat.

I was so delighted when these boots arrived that I wore them with my cargo shorts while cooking dinner. The Violet color is bright and cheery without looking childish. In the fall, I can envision them with leggings and a long tunic, or a short grey wool skirt and some black tights. For now, I’m just awaiting a rainy day so I can test these out by splashing in some puddles. It’s the hottest part of summer here in the American south, but already I am dreaming of autumn so I can wear these boots!

You can find Hunter Original Gloss boots at Zappos for $125, which is the same price as other places but includes free, fast shipping.

Cole Haan has a new heritage collection called Cole, Rood & Haan, which includes the name of one of Cole Haan’s original founders from the 1920s. These styles are a perfect fit with the renewed focus on menswear-inspired shoes (such as Marc Jacobs’ patent jazz flats from last fall), and the spring/summer 2010 line is absolutely gorgeous. This collection includes traditional saddle shoes, wing tips, soft chukka boots, deck shoes and sandals, but the Crush boots stopped me in my tracks when I first saw them in person.

Crush comes in black leather for winter, but whiskey leather and natural canvas with antique brass studs are incredibly charming. I think these are the perfect spring and summer boots. The golden color of the leather will age beautifully, adding a historical worn-in feel without looking shabby. The stacked leather heel, leather lining and wing-tip details speak of fine quality, while the side zip makes them easy to wear. I can envision these with denim capri pants or shorts, a long prairie skirt, soft linen trousers, or even a sweet sundress.

Cole, Rood & Haan Crush boots are available for $375 at the Cole Haan site (they offer free shipping) or in the CH retail stores. I haven’t seen them on any other sites or in other shops.

Oh, boots with buttons, how I love thee…there’s something about this old-fashioned style that really blows my skirt up. Frye’s version of the button boot is perfectly Victorian and modern at the same time, with piping and a round toe complementing a leather sole and curvy heel. The cranberry color is unexpected in a style this traditional, but it comes in four other colors, including slate grey and navy blue.

This boot has a 4″ heel, but the tiny 1/2″ platform means it is probably more stable and comfortable to wear than most high heels. The shaft measures 15″ – 17″, depending on where you measure from, and is decorated with antique brass filigree buttons. There’s an inside zipper in matching antique brass so you don’t have to fumble with all those buttons (most of us don’t have buttonhooks these days).

As with most things that are both beautiful and high-quality, the Frye Matildas are not inexpensive. At $450 they are not something you could realistically collect in every color, unless you’re independently wealthy or want to eat Ramen for dinner all winter. But the style is timeless, and Frye boots are made to last a lifetime, so they are a good investment. Go get ‘em at Zappos, Endless, or the Frye website. Note: Some reviews say that the shaft of this boot runs narrow, so if you can’t try them on before buying, check the specs and measure your calves before ordering to be sure they will fit.

They’re pink. They’re Christian Louboutin. They’re 40% off at Bob Ellis. What’s not to love?

Decollete is one of CL’s classier styles. The low, exposed sides give this style its name, but the graceful lines keep these 4″ heels on the elegant side of sexy. The suede version is also available in grey and red, but this sweet rose color is, of course, my favorite. I can envision these with ivory or tan trousers and a pink print blouse for work, with soft neutral summer linens for a date, or with a pretty dress on a special occasion.

As with most Christian Louboutin, you may need to go up a size. Try them on in person if you can, because CL styles vary in fit. If you order online, be sure you can return them if they aren’t quite right.

This is the time of year when I typically start looking for spring boots, and I don’t mean welly rain boots. Boots for spring seem almost counter-intuitive, but here in the southeast US, the weather starts to warm up in February. It won’t be sandal weather for a while, though, and I don’t necessarily want to expose my winter-white legs to the world just yet. Lightweight, neutral-colored boots are an excellent solution, and these Steve Madden boots fit the bill nicely.

It’s probably obvious that I have a thing for harness style boots, and the Buck style takes this a bit further with extra straps and buckles around the shaft. They give the boot a little bit of military style, while also making them somewhat adjustable – which is good, because there are no zippers. They are available in brown leather and black leather, but I like the taupe suede best for early spring. I can envision them with skinny jeans, a short denim skirt and tights, or even a softly flowing spring skirt.

You can find the Steve Madden Buck style at Endless.com or Zappos – and they are on sale in both places! For what it’s worth, the images on Zappos are more representative of the actual color.

Many people think that Revas are done, over, soooo last season. IMO, some things are destined for timelessness, and Tory Burch Reva flats are among them. Soft leather, comfortable, excellent quality, go with everything, and in all the colors of the rainbow! Revas come in plain kidskin, patent leather, suede, and metallic leather, and I love them all, but by far, the most eye-catching finish is mirror. These were also available last spring in Tangerine and Navy, but when I saw this incredible, rich Bougainvillea pink, it was love at first sight.

I love wearing these on grey, dismal days because they are cheery and make me smile. And it’s not just me. Every time I wear these shoes, people stop me to make comments, whether it’s in the office or on the street. OK, so comments aren’t necessarily compliments, but people are always compelled to say something. One day I wore them on the subway and some guy started laughing…and eventually confessed it was because of my shoes. I didn’t care whether he was laughing at them or with them, I just think it’s cool that they make people happy. Yay for happy pink shoes!

As long as we’re on the subject of boots…you can’t go wrong with the classic Frye harness boot. Frye is the oldest shoe company in the United States, and Frye boots were worn by soldiers during the Civil War, the Spanish-American war, and by Teddy Roosevelt’s Rough Riders. Many homesteading pioneers wore Frye Boots for the long journey from New England to the West during the 1800′s. Frye’s harness boots were first made in 1938 at the request of a US Navy admiral, and were supplied to US servicemen as “Jet Boots” throughout WWII. I first lusted after this style more than 20 years ago, and it’s still timeless.

I have a pair of these boots in black, which I stalked for two years before buying. I first bought a pair of inexpensive Harley Davidson boots that had a similar look, but they just don’t compare to the real thing. I tried on different sizes and colors of the Frye Harness 12Rs (denoting the 12″ shaft – they also come in shorter 8R and mules) until I’d found the right ones for me, and with their signature boxy toe and shiny silver hardware, I always feel both bad-ass and stylish when I wear them.

In the past, I’ve considered getting a pair in red, but yesterday I found Frye harness boots at Endless.com in no fewer than 8 colors. As soon as I saw them in this rich plum with a hint of brown undertone, I was smitten. I know purple is huge this season, but purple Frye harness boots are more than I could have hoped for – and with antique brass hardware, no less. They aren’t cheap, but at $198 including free overnight shipping, they are less expensive than many other boots this year, they’re indestructible, will never go out of style, and you can wear them almost anywhere. That’s my story, and I’m sticking to it.

So many boots…so little time! One reason I wait for cool weather to arrive in the fall is that I can start wearing my boots again. Something about them just makes me feel fabulous, and the taller the better.

Today I discovered Gee WaWa, a small artisan line of footwear. Many of the styles look like something I’d find in a vintage shop – kind of retro and well loved and funky — but still modern. These Tom Tom boots remind me of the amazing black/green Son of Sandlar boots I got at the Renaissance Faire this year: …but less costumey and more appropriate for street wear.

The semi-round toe and low stacked heel mean they would be comfortable to wear, and the soft ruffles and button detail make the Tom Tom style more feminine and keep the style from being too biker-y. I can see these with a little tweed skirt and tights, peeking out from under a longer skirt, or with jeans tucked in. I am not personally familiar with Gee WaWa quality, but they appear to be very well-made.

So where can you find these boots? Zappos has carried Gee WaWa in the past, but doesn’t have them at the moment. There is a Gee WaWa website, but they don’t do e-commerce there. For now, the best selection seems to be at Endless.com, where you can find Tom Toms in 3 colors and about 30 other Gee WaWa styles. The one thing to be aware of is that they reportedly fit narrowly in the calf. These boots are $280, but currently you can get 20% off at Endless if you buy 2 pairs of boots – might be worth it!

What can I say about Chanel ballet flats? Timeless elegance. Classy and un-fussy. These beauties are my favorites for this fall — two-toned in black and dark grey, with a black cap toe and elastic-edged uppers.

No giant logos to scream at you, just understated presence. They are perfectly appropriate (and comfortable) for work, but also utterly fabulous with jeans! Simply. Gorgeous.