If there was ever a classic look for cooler weather, it’s a pair of leggings, a long shirt and boots! This casual look is a crazy comfortable outfit and screams utility and style. And while many of us have a drawer full of our favorite comfy leggings to choose from, picking a shirt to wear with leggings and boots is a little bit trickier. Read on for my favorite outfit ideas (and scroll to the bottom for recommendations of the best leggings).
Tunic Top
Tunic tops (essentially just longer tops or sweaters) are usually the first thing most women think about pairing with leggings for one crucial reason: rear coverage! Thankfully more and more clothing companies are offering leggings that are thick and non-sheer but tunics are still a great option for this look, and a good alternative to short tops.
A solid color tunic is the obvious choice for patterned leggings but be aware that prints and a bright color tend to draw the eye and choose your outfit accordingly. For example, if you carry your weight on top, you might choose fun leopard print leggings like those pictured here and a basic solid colored tunic. Whereas if your bottom half is curvier than the top, you might consider basic black or gray leggings with a more eye-catching color or print for the shirt.
Don’t have a longer tunic or can’t find one you love? Try layering short dresses that you already have in your closet over a pair of black leggings! This combo is a super stylish look and makes summer dresses last all through the colder months as well.
Long Sweater or Sweatshirt
While a tunic is technically a top that comes past the bottom to your thighs, many oversized sweaters are designed to be a little longer and may be easier to find than a tunic. Plus, they’re warmer than T-shirts and combine with leggings and boots for the perfect fall or winter look.
I love it when an oversized sweater hits me right in the middle of my backside as that’s generally a look I like on my body type. But you might have to experiment a little to decide what length sweater is the most flattering on you. Just beware of picking something too oversized if you’re on the petite side. Long tops tend to drown smaller bodies and make you look less mature.
And you can achieve a similar casual outfit by trading out the sweater for a sweatshirt. I love a great graphic sweatshirt like this one but a neutral color sweatshirt is equally fabulous and even more versatile. Check the end of this article for great shoe choices for each different top but a sweatshirt and leggings combo goes best with more casual footwear. Think an open toe wedge bootie, sneakers or combat boots.
Button Down Top
A button down top will elevate any outfit involving leggings and there’s not much that doesn’t work well with a classic white shirt. Again, slightly longer versions of these tops work best with leggings, especially if you’re looking for bum coverage. And while you don’t have to choose a really oversized top, the best choices for button downs to wear with leggings are slightly less fitted than you might wear with, say, work slacks. Throw on a denim jacket to add some extra warmth and style, especially if you’re looking to transition that button down to more casual wear.
Wearing a white top buttoned up with classy boots can even be office-appropriate, but you might also want to try leaving a button down shirt open with a tank top underneath for a more casual look. This outfit works especially well with a chambray shirt; pair this combo with cowboy boots for a stylish western-inspired ensemble.
Crop Top
If you’re more comfortable with shorter tops and showing a little skin, crop tops are having a heyday right now, especially worn with leggings. High waisted leggings work best for this look and I’m a big fan of slightly baggy, oversized crop tops since more fitted varieties tend to make it look like you’re headed to the gym.
Throw on a long cardigan or leather jacket to add warmth and coverage. Plaid shirts worn open over a crop top is also a super trendy look right now, especially those made with thicker fabrics.
Shoes
So what kind of boots work best with these cute outfits? Almost any kind you’ve got!
• Ankle boots are a great choice for transitional seasons (fall & spring) because they’re not as warm as taller boots and they come in a variety of heel heights. My favorite is probably a 2″ wedge heel which gives me some height without sacrificing my ability to walk comfortably
• Riding boots are taller and usually come to the knee or thigh. These are probably the quintessential boot to pair with leggings because they require a really thin pant to fit inside them. I love them in a warm brown or cognac color but black boots go with almost everything and a tall boot adds lots of warmth for cold days
Too warm for even ankle booties? Lucky for us, leggings and a cute shirt look great with a variety of other shoe options.
• Ballet flats are not only pretty and feminine, they’re really comfortable, especially if your day involves a lot of walking
• High heels aren’t a great choice to go with basic athletic-wear leggings, but pair heels with faux leather leggings and you’ve got a smoking hot date night outfit
• Sneakers with leggings and a stylish top makes for the perfect errand or vacation outfit. I’m a huge fan of any colorful shoe style but you can’t go wrong with classic white sneakers either
Favorite leggings
If you’re new to this stylish outfit idea, you might still be looking for the perfect pair of leggings.
• Classic black leggings are a great place to start. You might even have some hiding out in your workout drawer that you can experiment with for everyday wear
• White leggings (or another light color) can be a really fun, chic look as long as you can find a pair that’s not sheer (or you wear them with a really long top)
• Black leather leggings (or faux leather) will create a higher-end look with the comfort of yoga pants.
• Fabulous patterned leggings (like these) are a great way to make a statement while staying ridiculously comfortable
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