What Would a Stylist Do?

Can printed pants ever be flattering?Absolutely! Keep in mind that the repetitive, smaller designs on dark backgrounds are more flattering, and are easier to combine with items you already have in your wardrobe.

What type of jeans work best with this season's shoe boot?In general, you want to wear them with a pair of skinny jeans that are hemmed a little bit above the top of the boot, says Hitzges. (You can also cuff them for the same effect.) If the jeans are too long, they start to bunch up, which can look messy.

What type of shoe would you wear with a long skirt?For the fall, I would go for a heavier shoe to ground the look for the season, suggests Hitzges. Stay away from really high stiletto heels, or open-toed shoes, which can look overly dressy in winter.

How can you wear pajama-style trousers without looking sloppy?The obvious answer is that you can't go too oversized, says Hitzges. But elevating the material—silk brocade rather than cotton, for example—is the ultimate way to polish the inherently casual nature of a slouchy pant.

What's the ideal length for a pencil skirt?Just above the knee is traditional and works really well for most body types, says Hitzges.

What should you look for in a timeless blazer?Something that hits mid-hip and is a bit oversized will be the most versatile, says Hitzges, who says it's fine if your top peeks out beneath the blazer's hem. Just be careful not to buy a cut that's too boxy, she adds.

How do you make your typical little black dress dressy enough for a special occasion?One of the easiest ways is to play with texture, says Hitzges. To start, look for a dress that incorporates texture in its design—sheer sleeves, or a raw, unfinished edge. Then add interest with accessories.