Last winter, I rediscovered the advantages of wearing long shirts and sweaters over leggings tucked into riding boots. This is what I wore when I took riding lessons in my 20s, and I've always liked the look. For a couple of years now, this style has been ubiquitous. And why not? If you're in reasonable shape and your coat or sweater is long enough to conceal whatever needs concealing, a pair of opaque, dark leggings are comfortable and warm as well as sufficiently hip. Chunkier boots will balance a heavier upper leg, and black leggings with black boots will give most women a longer, leaner look. Quality leggings provide shaping and hide flaws in ways that low- or mid-rise pants cannot. And if the opportunity presents itself, you can easily fling yourself into a saddle at a moment's notice and canter down the Comm. Ave. mall.
Back Bay society girls used to do just that into the early 1950's, I've read. You could still stable your horse somewhere in The Fenway in those days.
But I digress. A snug, properly fitted pair of jeans can never be truly comfortable because denim is a heavy, unforgiving fabric. (Looser jeans may feel better, but they won't look better.) Real denim is stiff and hard. And the softer, stretchier, lycra-blend jeans often start out snug but expand ridiculously after you've worn them for an hour. I have a pair of Anthropologie Pilcro skinny jeans that grow a size or two in no time after I yank them on. Even though they are a size smaller than I normally wear, keeping them in the vicinity of my hips is a steady part-time job.
You can have the same problem with some leggings, but usually not on the first day you wear them. I've found that you just need enough pairs to throw the stretchy culprits in the wash after one wearing. Fortunately, many good brands are inexpensive. I like Lissé leggings from Lord & Taylor; I wait until they're on sale. They not only stay put, they have a slimming, higher waist. One pair of mine has a super-high, empire waist; I wasn't paying attention when I bought them. They would not only cure a muffin top, they would conceal a late-term pregnancy.
I have leggings with a fly front and equestrian styling, made of the same heavy, synthetic twill I wore in my riding era. They look sharp, but the cheapo snap at the waist pops open all the time. According to the reviews online, this is happening to everyone, so I feel less embarrassed.
Hue makes all kinds of leggings — even bootcut and faux-leather styles — but their denim-y ones (I hate the word "jeggings") look convincingly like skinny jeans, with topstitching, working back pockets, and rivets. They're heavy enough for cold weather, and it's easy to zip boots over them. They're the best of both worlds: the look of jeans with the comfort of yoga pants. The trick with Hue leggings is to try a few sizes to get the best sleek fit, keeping in mind their "growth factor."
I have corduroys from Anthropologie's Pilcro line. These have convincing jeans styling, but they pull on. It's a fact that premium jeans fit and look better than garden-variety types, and this can be true even for leggings from those brands. Pilcro leggings work well for small-waisted, curvy women. Unfortunately, they also have that Pilcro tendency to inch downward during the day.
Some women solve this problem by making the elastic in the waistband tighter. I might try this. But I think someone could make a fortune by marketing some kind of high-tech, invisible women's suspenders. In the meantime, I have another solution for pull of gravity: stay inside, remove your boots, lie down, and read or take a nap. It's starting to feel like winter, so why not hibernate in those trendy long-johns you're wearing? Works for me.