Jonathan Saunders Ponte Mini Dress | $32.99 at Target

Jonathan Saunders Colorblock Top | $24.99 at Target

JNSDS Sleeveless Sweater Dress Cilantro | $34.99 at Target

Jonathan Saunders Knit Ponte Skirt | $26.99 at Target

JNSDS Woven Top in Grey | $22.99 at Target

A: When you find what works for you, our best advice is to stick with it.  Since you find that scoopneck tops flatter your figure, we encourage you to wear them all year round.  Here’s how to wear this summer weather top during fall and winter.

Instead of summer’s plain cotton scoopnecks, look for winter varieties in thin, warm insulating fabrics.  We’d recommend against chunky, bulky fabrics, as the volume on these tops will erase the figure flattery gains you’re getting with the scoopneck shirts.  Instead opt for fabrics that are natural insulators, such as silk.

But of course, thin fabrics aren’t naturally as warm as thicker fabrics.  To get the warming effect of a thick fabric with the look off thinner fabrics, dress in layers.  You can layer two (or more) thin shirts together to get the warming power of a thicker shirt or sweater. When you wear two thin shirts, you get the warmth of each of the individual shirts, plus the heating power of the warm air trapped in between the shirts.  Two are really better than one, especially if your undershirt is made of silk.

If layered shirts are still not warm enough for you, add a cozy sweater or cardigan.  You don’t need bulk for warmth if you’re layering - merino wool and cashmere are warm without necessarily being bulky.

Ruffle Bib Plaid Shirt | $48 at Gap
We’re loving the feminine ruffles on this pretty plaid shirt.  Pair it with something structured for a chic Fall look.

I don’t know what’s happening, but the level of sloppiness in what some guys are wearing is simply getting out of hand.  Loud colors, ill-fitting clothes, sunglasses at night– it’s not stylish, it’s sloppy.

If you want to look as if you don’t care, that’s fine, but please do it with style.

Or more specifically, with sprezzatura, the Italian term for “artful dishevelment” as I call it (it’s not a literal translation).  You may do it already without knowing: sprezzatura is dressing like you don’t care, taking a nonchalant attitude with your appearance—when in fact you do take time and effort to create your look. 

The trick to pulling it off is subtlety, confidence and an otherwise impeccable outfit.  Let’s examine probably the greatest example of sprezzatura, Mr. Gianni Agnelli. Look at this picture of Mr. Agnelli in deep thought.  What is peculiar about his outfit?

Look carefully…do you notice his wrist?  It’s more apparent in this photo because your eye is naturally drawn to that area, but it has to do with his wristwatch.  Mr. Agnelli would often wear his watch outside his shirt cuff but under his jacket. 

The trick to successful artful dishevelment is twofold: subtlety and great sartorial know-how.  Imagine meeting Mr. Agnelli.  Would you even notice the watch?  Only if you looked carefully.  And that’s the point: the fashion quirk is subtle and understated.  If Mr. Agnelli didn’t comb his hair or if he wore an extremely wrinkled dress shirt, the dishevelment would no longer be “artful” but simply sloppy.

But even more important is that Mr. Agnelli’s suit is impeccably well cut.  He has great sartorial knowledge and flawless taste—and it shows.  If he wore an ill-fitting suit and a strange shirt/tie combo, people would consider him sloppily dressed.  But because his suit fits him perfectly, he still looks sharp.  That’s the fine line between artful dishevelement and simple sloppiness.

First of all, notice the loosened tie.  Many men do this out of comfort, but they don’t consider how sloppy it can look.  But when Mr. Bastian does it, it looks stylish. Also, notice his jacket cuff.  See the two buttons unbuttoned?  Finally, look his unbuttoned jacket.  There’s a style “rule” that suit buttons should always be fastened whenever you’re not sitting.  Mr. Bastian looks like he’s giving that rule the proverbial middle finger.  You know he knows that rule, but he doesn’t care.  Sprezzatura is as much about confidence and attitude as anything.

I’ll share one more sprezzatura example: Stefano Tonchi.

Take a look at two things: (1) the single button fastened on the jacket, and (2) the part of the collar outside the jacket lapel, but not in a Tony Montana kind of way.  That’s his subtle quirk; what’s yours?

Notice in all three cases the lack of obnoxious wear: well cut suits with no loud colors, and confidence without cockiness.  That’s what separates these three from the average guy at a club on a Friday night.

It’s hard to look like you don’t care when you do.  When it’s done wrong, you have stereotypical “Los Angeles fashion”; when it’s done right, you have Mr. Agnelli, Mr. Bastian, and Mr. Tonchi.  It’s the difference between sloppily bad and eternally cool. 

Style tip? Steven Alan produces a great line of shirts that come wrinkled (if you’ve never seen a display of his clothes, they even hang on the rack at stores wrinkled and creased).  These shirts are a great place to start if you’re trying to get a feel for this sprezzatura.  But the bottom line is that true sprezzatura can’t be done for you and no one can tell you how to pull it off; it’s about feel.  And it varies from outfit to outfit; a wrinkled shirt in one outfit won’t necessarily look good in a different outfit. 

The other key way to manage your height is to choose garments with horizontal details.  The horizontal details draw the eye from side to side, which will help to visually shorten you.  Look for horizontal stripes, horizontal seamlines, and any other details that visually cut your body widthwise.

Layering is going to be your friend as you put your outfits together.  With your height (and your age), you have the opportunity to experiment more with layering.  Pictured is a simple fashion formula that you can play with: a drop waist coat, a long sweater that hits at the hip, a top with horizontal details, wide-leg jeans, and flats.  When the weather gets chillier, add a colorful scarf to the outfit for extra color and texture.

(2) Color coordination ties the outfit together.  The yellow patterned tank is surrounded by an adjacent hue, orange, both in the form of a hoodie sweater and a pair of standout shoes. A brown handbag picks up the brown in the tank as well. 

A: It’s common to be uncomfortable with pattern and color–it’s just so easy to fall back on the safety net of black or other monochromatic neutrals.  Though these neutrals are easy, they’re not always the most flattering.  Even neutrals can visually drain color from your face–and they leave you as a bit of a fashion wallflower. 

How to Choose a Pattern
Be sure the pattern is scale to your own proportions.  Petites should look for small patterns so as not to overwhelm the body.  Those with larger frames, however, would look frumpy in small, delicate prints. 

How to Choose Colors for your Patterns
Choose colors that enhance your own coloring.  How do you know what colors work for you?  Here’s a simple test: Hold two pieces of construction paper under your face: one orange the other pink.  Whichever color softens your features and lessens shadows on your face is the tone you should look for.  If orange works better for you, look for warm colors like reds and oranges.  If pink makes you look better, look for cool colors like greens and blues.

How to Wear Pattern
An easy way to ease pattern into your wardrobe is through accessories.  A scarf added to a solid dress or dark suit adds a pop of life.  Look also for patterned belts, tights, and handbags. Once comfortable with pattern on accessories, you can move on to blouses, skirts, and even dresses.

The easiest way to wear a pattern is to wear one single pattern against a backdrop of solid colors.  Pick a color from the pattern to wear as your primary solid color. For example, if your sweater is red, yellow, and pink, you can pair it with a skirt that’s red.  Note that the shade of red in the solid colored skirt doesn’t need to match the shade of red in the pattern.

(1) Start with your basic summer chinos.  
(2) Add a basic button-down over a solid colored tee.
(3) Slip on a henley sweater (or a cardigan).
(4) Finish off the outfit with a sharp pair of oxfords.