An essential summer-to-fall transition piece, the lightweight cardigan adds enough warmth for cool mornings and evenings and fits neatly into a purse when temperatures soar midday. This M-perfect floral style from Charlotte Tarantola, known for her sprightly cardis flaunting vintage-inspired feminine details, has cascading ruffles and a row of jeweled buttons that make the waist appear smaller. The ruffled neckline also accents the collarbone and frames the face. Wear it with jeans and heels for movie night, a pencil skirt or sheath dress for work, capris and a tank for a Labor Day weekend beach trip…and it would look stunning with a turquoise handbag and gold shoes or vice versa.

Suddenly, it’s getting darker earlier and some of us are reaching for a blanket at night. Fall is hovering at the edges and bringing with it a rich array of gorgeous, supple clothing. Talk about fashion’s siren song! There’s no resisting it. And, of course, we all want to wear our autumn picks now. You can with a transition layer, and this knitted, hooded tunic is perfect, Y. The deep V-neck minimizes shoulders and provides the perfect frame for a stunning necklace. And that tantalizing berry color looks good on just about anyone. Right now, we see this in a mix with chic shorts, gold-tone sandals and a cami layered beneath. For fall, a simple silk blouse, jeans and boots.

Given the vagaries of Mother Nature and indoor climate control, your wardrobe may occasionally exhibit a sartorial schism (Hello, Sybil!) that leaves you to swelter in a turtleneck or to shiver without sleeves. This makes it imperative to have smart, versatile pieces that can support layered looks and weather multiple forecasts. Ms. S, consider a slightly tailored, mid-weight cotton skirt with trans-seasonal classic dots. Sunshine? Pair it with a tee and sandals. Rain? Try a trench coat, tights and yellow wellies. A defined waist and light fullness at the high hip highlight hourglass curves, while a close-to-knee length handles the in-between days with aplomb.

Getting antsy for fall, H? These lightweight, cotton-blend ankle pants will let you transition your style now without feeling overdressed. The slim, tapered leg works well with a shape that’s straight, playing up lower-body curves by emphasizing the difference in width between the hip and ankle. The belt delineates the waist, and we suggest adding a black, white or bold top for contrast that breaks up your figure—perhaps a cotton shell while the weather’s still warm or a long-sleeved shirt when autumn finally arrives. As far as footwear’s concerned, sandals, flats or heels are all acceptable with this pant silhouette, making it surprisingly versatile.

Fall fashions are beckoning from every store window, website and fashion mag. Just looking at them is like a shot of adrenaline on a hot summer’s day. And for many of us, September 1st is the real New Year’s Day. So pop a champagne cork a little earlier, A, by picking up something that can be worn now and later. First, select your color palette and fabric. Linen—even knitted—is wonderfully cool, and this vest is sartorial and light enough to layer come fall over a lovely tie-neck blouse or long-sleeve tee. It pairs with anything, even a shirtdress. Right now you could wear this on its own, but layering a cami underneath in a complementary color would add interest. Or unbutton the placket to create a little more neckline attention.

It’s August. So how about a cozy, mostly cotton, wee-bit-wool sweater to snuggle up in? There are enough chilly nights and over-air-conditioned offices to keep this lovely cardigan busy through the end of summer and, of course, beyond. Layer it over a pretty top and preferred summer bottoms now. Later, pair it with jeans or a prim, ladylike dress. (Nothing plays up a “grandfather” sweater like a pretty frock.) Because of the deep neckline and easy, shawl-like collar, your main assets, P, will look quietly sexy. The patch pockets also add visual weight at the hem to fill you out where you’re lean. The verdict on this lovely transition piece? Go ahead—give it a cuddle.

Ms. E, we could philosophize that life is all transition. Or we could simply salute the sleeved dress, a wardrobe warrior with a versatile, wear-it-now and wear-it-later attitude. Notice how short or cap sleeves provide the coverage well suited to a multi-seasonal, work-worthy look. A fitted bodice and an empire waist highlight upper proportions, and a soft, fold-over collar draws attention upward. A light, neutral plaid pairs well with summery peep-toe pumps, along with fall-friendly cardigans and closed toes. Go modern with a bright tote bag, or add a clutch if you’re in a Mad Men mood—versatility ensures effortless transition.

You’re interviewing. Again. So how can you inexpensively update your usual job-hunting garb? More important, what can you wear that will make you stand out in a good way? Ms. M, may we suggest swapping in this ivory and black polka-dot blouse? The center ruffle modestly accents the bust and then narrows as it descends, which, along with the V-neck, creates a waist-slimming visual effect. And unlike a plain white button-down shirt, it adds graphic interest to a black suit while still communicating, “I’m organized and dependable.” It also prevents a potentially severe “I’m in the FBI” impression. (Of course, if you’re interviewing with the FBI, by all means stick with the button-down.) PS: This top also comes in petite and plus sizes.

When going through the interview mill, you tend to wear the same suit over and over, so tops become crucial. It’s always advisable to stay conservative, especially when it’s a first interview or you’re job hunting in a conservative industry. On the other hand, conservative doesn’t mean boring or unfeminine, Y. This lovely sleeveless, jersey top skims over the body, making it easy to wear under a suit. And the gentle tie neck is feminine, drawing attention away from the shoulders—without being frilly. Prefer some color and longer sleeves? It also comes in lavender with an elegant three-quarter sleeve.

An interview outfit is a lot like a bridesmaid’s dress. It involves thoughtful selection, Ms. S, and chances are you (a) hope to wear it again or (b) want to stash it away ASAP. Suppose you already have a suit, all monochromatic angles and sincere lines. A cowl-neck blouse can provide an effective counterpoint. Soft silk or fine-gauge jersey can define curves without unprofessional cling, and subtle luster creates reflection and shadow, drawing the gaze upward. The simplicity of this style lends itself well to professional first-impression dressing but will also work with casual Friday looks after you’ve landed the job.