Q: Is it sloppy not to tuck in a button-down shirt for work if you're a woman? What are the rules here?
A: Style "rules" are merely guidelines, so remember that you can always bend and break them as you see fit. That said, here's what I know about tucking: Button-front shirts were once tucked by women and men in all professional situations, but style preferences have changed. Nowadays, lawyers, C-level execs and other suit-wearing folks are still expected to tuck. The rest of us aren't, and generally don't. So long as your shirt fits properly and is freshly pressed, it will be office-appropriate worn untucked. Since wrinkling happens organically when you wear a shirt, consider wrinkle-free fabrics to minimize your level of midday rumpled-ness.
Be aware, though, that your tucking preferences may be proportion-dependent. We expect to see a longer torso line with pants, so untucked button-fronts usually look natural with them. We expect a shorter torso line with skirts, so tucking may work better. Of course, if you just plain prefer the look of a tucked shirt, by all means tuck. And if your generation sees untucked shirts as a sign of slovenliness, tuck your shirt and do your best to give your untucked colleagues a pass.
Q: What's the word on matching your skirt or dress hem to your coat hem? Do they have to be the same length, or is there wiggle room?
A: Wiggle room. But with caveats. When dealing with different hem lengths, make sure it looks intentional. A dress that peeks out a couple inches below a coat hem will likely look fine. The hemlines are close enough that they don't compete, and they won't divide your figure into awkward chunks.
On the other hand, a mid-calf skirt and a mid-thigh coat may look unintentional. Two low but markedly different hemlines will monkey with your proportions and break up your silhouette. Any mid-length coat that covers your skirt hem in its entirety will work, too, but if you can't get your skirt within a few inches of your coat hem, go much longer or much shorter. A cropped coat will work with any skirt because it's clearly meant to hit high. A full-length coat will work with anything from minis to maxis because it offers coverage down to the ankles.
Q: Anna Wintour routinely wears a variation on a sheath dress. Is that a signature or a rut?
A: We need Anna to weigh in, and here's why: The difference between a signature style and a sartorial rut is how you feel about it.
Are you buying the same things because you can't think of anything else? If so, you're in a rut. Have you identified a garment that works for your style, and feel content to tinker with minor variations on this theme? If so, you've developed a signature. Consider, too, if what you're wearing truly suits you. Many of us get stuck in ruts wearing outfits that are more easy than appealing: jeans and a tee, trousers and a cardigan. We wear them constantly even though they don't work for our figure or style. A signature is a style or garment that you gravitate toward or even collect because you love how it works for you. In a rut, you feel bored and frustrated. With a signature, you feel pulled-together and confident. I'm betting our girl Anna falls into the latter category.
Sally McGraw is a Minneapolis-based personal stylist and creator of the blog, Already Pretty (alreadypretty.com). Her fashion advice appears on this page once a month. Send your questions to: email@example.com.