Flick Flack in Black by Irregular Choice

Now for Something Completely Different: Irregular Choice's Flick Flack is a happy mash of styles.

We picked up Irregular Choice for fall and it immediately lifted out spirits. The company philosophy is to create shoes that "supply something fresh and fun that maintains imagination and originality above all else." The Flick Flack's eclectic mix of materials and styles places a premium on imagination and, better yet, makes us walk with a smile on our face.

The black patent upper sits on a 3-1/2 inch heel that rounds forward into a cute mary jane toe. The leather upper is topped with a double-faced fabric cowl – black and white ticking on the outside and white-on-black polka dots on the interior, which flips over for a rakish break of the shoe's silhouette. Three spat-like, cloth-covered buttons keep it secure. The inside? Crushed pink velvet! The heel and footbed are perforated. The sole is a riot of color featuring the Irregular Choice icon.

At first glance the shoe feels like a jumble of parts. As we wore it, we saw how each part related to the others. Perforations worked back to the polka dots. The dots were a riff on the reversed ticking opposite. The ticking played against the smooth, round toe. Cloth and leather did the same dance. The velvet? Pure fun, and why not? (Not everything needs a rationale.)

Irregular Choice lives up to its name: it's not a typical Lori's shoe and we like that. This shoe is young, fresh, fun. In a season of boots, this pump holds up. It has conservative lines topped with bold verve. Forget your jeans, these shoes demand skirts with structure or body to bring out their playfulness. It may be an irregular choice in our catalog, but this season it's a sure look for fall.

24053 Brown by Janet and Janet

Here Comes the Cavalry: Janet & Janet put spurs to the Western look.

Janet & Janet, one of our Italian Exclusives lines, consistently turns out fantastic boots. The delight is in the details with the 24053, a Western boot that with rounded toe, clean lines and belted shaft feels more cavalry than cowpoke. The stitching comes in single and double rows, turning a mode of construction into finely illustrated texture. A reinforced heel tab, top pulltabs, leg cinch and vamp are all carefully curved to lend this utility boot feminine grace.

Then, the leather. It's so supple we want to fold it up and take a bite. (Don't worry, we behaved.) The quality is fantastic. A gold leather lining a nice surprise. This boot is sensual. We want to caress this boot until we maul it. The dusky mud brown simply begs to be scuffed, roughed and worn into weathered beauty. We might buy this boot to wear now, but we're thinking of how wonderful it will look in a year or two. And with a leather sole and stacked wood heel, your cobbler can make sure it lasts at least that long.

Not all is rough and tumble in this Spaghetti Western: the vamp and heel cup are delicately finished with dark burgundy piping. A thin brass plate finishes the heel where it meets the sole, a fashionable vestige of spurs and harnesses. Pick up this tiny detail with big metal accessories. As for outfits, this boot fits into pretty much any look. The straightforward silhouette is functional with a feminine lean; it's the agglomeration of those tiny details that let this boot prop up pretty much any personal style. One final, tiny detail: expect to go up a half size.

Vamp by Restricted

Triple Take: Vamp by Restricted is a over-the-knee worth another look. Then another.

With nearly two feet of taupe suede perched atop an adorably feminine cone heel, the Vamp is a glam gam boot that has us very excited for cooler weather. "Versatility" is a byword of the season, and Vamp is certainly that. We'd wear this three ways. Flip the cuff up for a full over-the-knee look and pair with brilliant leggings and a mid-thigh dress (seen above); flip down for a sexy buccaneer knee boot you can wear with skinny jeans; or scrunch the supple upper down and down for an everyday sophistication.

However you wear it, the carved wood heel props you up 3-1/2" inches: tall, but manageable. A narrow toebox keeps your feet looking petite and demure. That opens up opportunities for more daring styling with the upper, like experimenting with hemlines and leggings. The unstructured lines of the shaft can play nicely off an A-line skirt or a structured bag. The genius of this boot is how it manages to lengthen your lines without conforming to them. It's like an unexpected jazz riff on a tried-and-true tune; it arrives from nowhere and it just works. The Vamp is sexy because it's easy and confident. The embellishments of spring have melted into the silhouettes of fall. It has certainly seduced us this season with its easy chic and urban charm. Try a pair with our huge selection of leggings for a new fall look that will definitely mature into a classic.

All by Jeffrey Campbell

Urban Combat: Jeffrey Campbell's All brings down the house.

Boots are awfully big for fall, but even Jeffrey Campbell might show a little hubris dubbing his new combat boot the All. Then again ... it does have a little bit of everything we love. To start, this nine-eyed, paratrooper-style (side zip) combat boot is made from incredibly supple and washed leather for a weathered look that feels vintage '44. Details are standard issue as well: double-stitched captoe and reinforced heel and a spat-like upper over a vamp that unfolds into a delightfully floppy tongue. Modern upgrades include fat, waxed cotton laces, a laminated leather sole and one-inch heel, and antiqued ring pull.

We're focussed on the Khaki (over the Brown) because of its slight olive cast, as though we'd been scuffing our feet through the forests of the Western Front (or at least scrubbed them a bit at the local park). The Army green is a versatile neutral and the combat style – a classic elevated back into Trendland – works tirelessly for your outfit.

We say wear it loose, open, unzipped, flopped out. Hunter style. Laces uncinched, tongue hanging out, jeans tucked in. Let it display its personality. As the weather turns cooler, tighten up and don the leggings and skirt. Even cooler: baggy boyfriend jeans cut up and cuffed up. By now you've scuffed up those toes peeking out from beneath to look like a veteran of chic urban trend wars.