Hi there! Thanks so much for coming by today. Leggings have been a wardrobe staple for as long as I can remember! They’re easy to style and comfortable – what’s better than that, ha! Leggings can be worn in so many different ways, which is why they’re a great piece to have in your closet. Depending on what leggings you have, you can wear them for totally different occasions too.
You don’t always have to wear your leggings with sneakers. You can create a timeless outfit with leggings and a pair of boots! So, today, I’m sharing a roundup of shoes that you can wear with your favorite leggings, and the leggings I think they’d look nice with.
Six Shoes To Wear With Leggings All Year
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My outfit here is something I wear to be comfortable when running errands. I wore this look right after I had my baby! My feet were still swollen, so these sneakers were perfect to pair with my cashmere socks and leggings. A tailored coat like mine will add a lot to an otherwise casual outfit.
Combat Boots
It’s cold outside right now, so I’m starting us off with weather appropriate shoes to wear with leggings. Combat boots look so good with black leggings. I love the look of combat boots, leggings, an oversized sweater, and a blazer. It’s an easy and chic off-duty look that you can wear pretty much anywhere. The boots and blazer will instantly dress up your look, so you could even wear this out to a nice dinner. Wear your favorite jewelry to finish your outfit.
If you’re wondering what these boots look like in person, I also wear them with jeans and a skirt – click to see them on me. I’ve been wearing them everywhere since I bought them this winter!
Sneakers: The Most Obvious Shoe
Okay, this is a totally different vibe than combat books. I’m sure you’re thinking, yes, of course you can wear leggings with sneakers. But, I had to include them because sneakers are the easiest thing to pair with most pairs of leggings. Plus, you can make a really cute, casual outfit with sneakers and leggings! I’m sharing my personal favorites that I wear with my leggings! Click here to see one of my go-to ways to style this type of look when it’s cold outside. I wear each of these sneakers below with my favorite Lululemon leggings.
Sneakers and leggings also pair perfectly with socks. You can wear socks over your leggings for a super cozy look, or just wear your leggings over your socks. I do both with the socks I’ve linked here. Right now, I have three favorite pairs. For fall and winter, I live in this cashmere pair. I also wear this pair all year. I just purchased these because I noticed a few of my old socks had holes in them! It was time to retire them. Anyway, these scrunch socks are super comfortable and actually perfect for leggings. I’ve linked them all below as well, plus some others. I love how many different color options there are for each pair!
Knee High Boots
Knee high boots and a pair of leggings is a classic outfit that you can wear anywhere. It’s definitely work appropriate for a business casual or casual office, but it’s cute enough to wear on a weekend. I’ve been eyeing these boots in the outfit idea below, and I think they’d look perfect with leggings. I love suede shoes, and the color options are all gorgeous. While I used the taupe for the outfit idea below, they also come in a lighter suede called sandstone, as well as black!
I first purchased these leggings some time around 2008. That is what you call a closet staple, ha! They’re the best, and I’ve featured them throughout this post. I will say, they are a little bit too heavy to wear in the summer in most places. Otherwise, they’re something you can wear all year, and you can wear them with any shoes. I’ve worn them with knee high boots, sneakers, and loafers too. This particular pair of leggings has a small zipper up the back, so you need to cover your bum with a shirt, blazer, or jacket if you wear them to work!
My exact sunglasses are the second pair I linked – click here to see them on me. The first pair are a similar vibe at an affordable price.
Ballet Flats
Ballet flats are everywhere right now, but I see them as a versatile closet staple that will never go out of style! I find myself turning to ballet flats year after year – and season after season. I put together an outfit idea below with these burgundy ballet flats, which are definitely a classic pair of flats. I included them in this blog post because I think they’ll look cute with leggings, but they will also look nice with jeans, a skirt, or a dress. The color is such a chameleon that it will work with black as well as tan or brown.
This long button down is a thick cotton, and it’s really perfect to wear alone in the spring or fall. You could also layer it throughout the seasons.
I also linked a cute black denim hat that I would wear if I was wearing this on the weekend! I have a black denim hat from Alo that I wear all the time, but it’s sold out right now. I actually love the denim hat that I linked because it doesn’t have a logo!
I included a few other ballet flats that I love and think would look cute with leggings.
Chunky Boots
Just like combat boots, chunky boots might not be your first choice to wear with leggings, but I think they should be! They will elevate your leggings instantly. Chunky boots are typically a little bit higher than ankle boots so you won’t have an awkward gap between your shoes and your leggings. (However, if you have longer leggings, I love these ankle boots).
If you are looking for a shoe option to wear with leggings for travel during fall, winter, or spring, I would definitely consider chunky boots. They’re ideal for a day where you want to look nice but you’ll be doing a lot of walking. I wear my chunky chelsea boots all over the city! The pair most similar to mine are linked here.
This is an easy outfit to wear on weekends, whether you’re running errands or heading to a coffee date. A monochrome look will never go out of style. I know most of the looks here are built around neutrals. While I love a fun pop of color, going for neutrals with leggings will give your outfit a timeless look.
Loafers
Loafers come in so many different shapes, colors, and materials that you are sure to find a pair you love. I always go on and on about how wonderful my Sam Edelman loafers are. I wore them on a trip to London last fall, and I didn’t even have to break them in for a minute. I walked a lot of miles in those shoes right away. It was incredible! These loafers come in black and many other color options, but I think black leather loafers in particular look really beautiful with black leggings.
I included a couple of lightweight jacket options as the final touch for this look – there is always something about a top layer that adds an extra bit of elegance to a look when layers are appropriate. I recently purchased this jacket, which is another good option for this look, in a different color and material combination. Click here to see it on me.
Loafers are the perfect shoe to dress up your leggings for spring and fall, all while looking super chic!
Cozy Boots & Slippers
The last shoe I recommend is similar to recommending sneakers – cozy boots and slippers are obvious to wear with leggings, but I had to include both. I turn to my Ugg boots a lot for doctor appointments, walking the dog, and that sort of thing throughout the winter. Leggings and cozy boots or your favorite slippers are a classic pairing!
I hope you found a good shoe option to go with your leggings! Let me know in the comments what shoes you like to style with leggings.
