D53 by Ripicca

Become a Convert: Ripicca's D53 is two boots – and two looks – in one.

One thing you gotta give the military: they're pragmatic. Not a lot of flowery embellishment in the armed forces we daresay. And while efficiencies may be a theory espoused more than practiced, we're happy to see the concept spill over into our fall fashion. The D53 by Ripicca is one of many shoes this fall to embrace the military look but one of the few to capitalize so well on its practical nature.

The practicality starts with boots on the ground: a satisfyingly hefty lug sole has enough grip to let you march on the slickest of surfaces. We burned out on the lug sole about a decade ago, but a ten-year breather freshens them up. The D53 also taps into what's being called the "spat boot" or "collared boot"—a turn-down on the shaft that reaches past the ankle to cover the arch. What's so lovely about this taupe spat with twin buckles is that it is removable: flip a snap at the back heel and, voilà, you have a decidedly less-military black Chelsea boot. If the D53 is your soldier look, this Chelsea is your outfit on leave. In civvies, so to speak, the D53 is a classic ankle boot that can work back to pretty much any outfit.

Wear these to work looking all sober and responsible, pop on the sleeves in the evening and you're ready for happy hour and then some. Sleeveless, try them with jeans or even office attire—the lugged bootie is a great choice for commutes through inclement weather. With the taupe spat on, we're feeling more of a shorter skirt or shorts look (leggings depending on the temperature and your frame of mind).

We also take a cue from our guest bloggers Valerie and Camilla of A Butterfly by Day. They pair military looks by Sam Edelman with softly feminine silhouettes, patterns and hairstyles to break up the regimental tendencies of such boots. The result is sweetly complex and a blast to wear. The point being that the D53 blends classic boot shapes with inspired military touches to give you a whole bunch of something you don't often find in the army: options.

Dixie by Sam Edelman

Just Add Black Lipstick: Sam Edelman's Dixie ain't just whistlin' about the over-the-knee look.

Well at least this fall will not be boring. Over-the-knee boots, a huge trend in Fall 2009, is ramping up to be even bigger (or is that taller?) this season. While fall is always boot time, we had an inkling that booties and shorter styles would be the dominant boot. But taller and taller styles keep arriving ... and leaving in UPS boxes bound for excited customers. Sam Edelman's Dixie takes the look to a level that strains the definition of "over-the-knee" and conjures thoughts of hip waders.

When our boyfriends go to buy new suits (and this is indeed a rare occasion), there is a rule of thumb to determining a good fit. Don the jacket. Stand straight with hands loosely cupped. If the edge of the jacket hits at your fingers, it is the right size.

The same measurement can be used for these boots. Striking at mid-thigh after 22 pairs of eyelets, the Dixie is an incredible tower of badassedness. The upper of the boot has solid military/combat styling on a lug sole. The shaft rises past combat, past engineer, past logger lengths to something just ... vertiginous. At $322 they are not our cheapest boots, but consider this: you won't need pants. (Oh! The savings!) A simple mini works. Tights are perfect. In the past we've layered these over a purple bootliner and teal tights with a black mini skirt. The look is a dark, dark Mod. It is very sexy.

This look is edgier than a Chinese throwing star so respect it. (Edgier, but not difficult: a side zipper saves you the torture of unlacing to get in them.) Vintage denim jackets, fingerless gloves, biker gear = yes. A short trench over a mini and tortoiseshell  glasses, neck scarf, dark glasses ... you got us at "trench." Aggressive! We could also see some Madonna-inspiration (of "Desperately Seeking Susan" era) working here. Hell, find some coquettish plaid, a shrunken sling bag and Sharpie Xs on the back of your hands to wear it like a straight-edge lumberjack. These boots may be specific, but because they grab so many elements from military looks, Goth styling, punk and work gear, you can bend that specificity to your wardrobe whims. Go wild. These boots are already there.

Toughen-Up by Poetic Licence

Is It Tough Enough? Poetic Licence's Toughen-Up is a riff on Victorian button-ups with a modern twist.

In England they must call this shoe the Stiff Upper Lip—it certainly has a heavy Victorian influence that we cannot ignore and must instead love. The Toughen-Up riffs the Victorian button-up boot, but deposits it squarely in the modern world. For one, you don't have to actually button it up. (This alone will save you 15-20 minutes.) However the buttons are operable and, as in a men's suit sleeve, working buttons are a sign of extra quality. Another modern touch is the nod to collar boots—boots and booties with a fold-over that extends all the way down the shaft to cover the upper and some heel. This creates a great silhouette and the extra material feels luxurious. (Also luxe is the metallic leather lining, but that's a private luxury.)

A 2-3/4" stacked heel is modest; Toughen-Up makes its mark not by height, but by details. We love the leather-covered buttons, the sawtooth edging on the fold-over and cap toe, the slightly Americanized snub toe which seems a compromise between a Western squared and an English equestrian. Other compromises also work for you: the shaft circumference is perfect for layering in leggings or a thicker sock and the middling boot height plays well with short jean skirts or a full jean, tucked or over.

Did we mention the leather? That's because we saved the best for last. This boot is so supple you'd think it were rubbed with butter (it's not). It proved to be a bit of a pain to photograph it was so melty. What that means for you is a die-for comfortable, easy, forgiving fit. You can probably even scrunch Toughen-Up a bit for a casual slouch.

Collar boots, vintage looks, short boots ... these are all the qualities of fall in 2010 and they are all present in this one beaut of a boot. Between the detailing, the buttery (but, we stress, not buttered) leather and the smart construction, Toughen-Up is the way to beef up a 90-pound-weakling wardrobe.

Bronte by Matisse

You Can Be My Heathcliff: The Bronte by Matisse is a darkly romantic fall hit.

Booties. They're big in popularity if not physical stature. There's something about the swift cut of a bootie across the ankle that is so pretty and so wonderful with leggings. They are magnificent with skirts. And shorts. And, well, they just work which is why every fall we're excited all over again to see them. The Bronte by Matisse is no exception. Although, maybe it is. Is it even a bootie to begin with?

The short answer may be no. Built on a slightly chunky heel with chic, sweeping lines, the upper has a typical conservative pump construction: closed heel and round mary-jane toe, medium heel height. A raised seam at the toe is the sole embellishment.

The exception comes above. Attached to the leather is a double-faced, canvas sheath secured above the ankle by elastic. The unstructured, organic look and feel of the canvas is a welcome contrast to the structured look of the shoe. Like its namesake author, there's a Victorian echo to the shoe's silhouette, but its elegance is born of the tension between the soft romantic bootie and the structured, classic upper. That offhand gloss simple means it's a killer shoe with leggings and skirts. Love the way Bronte blouses out from the foot to come in tight against the ankle. That bit above the elastic makes this shoe like a present around your foot. There's some structure here, some slouch. It's as multi-faceted as you are.

Kit it out the same way: structured bottoms and softer, unstructured fall tops in cashmere or fine wools. We'd insert a scarf or cowl neck at this point since the weather seems to have broke for the moment. Jewelry's fair game. The neutral palette will work with pretty much anything you throw at it.

Nervous by Charles David

Glamour-ous Pumps: The Nervous by Charles David is a low-heeled must-have for fall.

You know, we're biased. Our tendency in this blog is to praise and laud shoes. We may come off as slightly subjective. Then again, what are we, the New York Times? But in all fairness we thought we'd offer a second opinion: Glamour loves the Nervous by Charles David too. In their September 2010 issue (p. 179), the magazine declares "Lower Heels Are Back!"Amongst the Jimmy Choos and Stuart Weitzmans perches our dear Nervous.

She sports a two-and-a-half-inch heel – modest but not mousy. Higher than the kitten heels on the runway (so says Glamour) but not vertiginous. A sleek, swept slingback contrasts with an inverted seam on the upper's front. The two provide movement and a bit of texture. The nude/neutral palette makes it an easy choice for professional situations.

For several seasons now, Lori has been trumpeting the return of the "classic pump" – clean and simple lines, a closed toe, modest heel. The workhorse shoe. Seems like the industry is finally catching on. The Nervous has some flare, to be sure, but it's detail in the service of enhancing your look. Those reversed seams? They work in tandem with the sling to narrow your foot and draw attention up to you ankles. We'd pair this with a pencil skirt or other short dressy skirt to pick up on it professional vibe (you can then extend it to pro or sophisticated casual as you see fit).

We like this pump. Glamour likes this pump. Pick up a pair and try them on. We're pretty sure you'll get a kick out of a classic look with some details that will knock your socks (trend alert!) off.