About These Flare Jeans

You can recreate these flare jeans outfits with any pair you already own. But if you want a pair that makes it super EASY to look good with minimal effort, I highly recommend this pair from Kohl’s.

I’ve talked about them so many times because they’re that good! They’re comfortable — thick and supportive, but still stretchy and easy to move in. The lines are clean and polished, and the dark wash takes things up a notch. (Dark washes are easy to dress up OR down, which makes them more versatile.)

• The dark wash is ultra versatile. It leans dressy and classy right away, but it’s easy to dress down too.
• The flare is flattering without being dramatic. These aren’t bootcuts — they don’t hug the knee as tightly, and they flare more noticeably, which helps balance out your figure.
• The fabric is supportive AND stretchy. You get that thick, structured feel (which helps hide lumps and bumps!) plus just the right amount of stretch. Best part? The rebound is amazing. These don’t sag out during the day — they keep their shape and keep you looking polished.
• They’re super affordable — often on sale for just $31.99! 🙌 You can find them HERE. I wear size 6.

This is the kind of wardrobe staple that will stay in style in your closet for YEARS to come!

How to Style Flare Jeans

If you’ve ever wondered what to wear with flare jeans, the answer is nearly anything!

I’ll show you a few formulas to create outfits with flare jeans that you can use over and over to create outfits on your own.

SIZING: I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes.

Dressy Flare Jeans Outfit: Blouse + Pointed Toe Pumps or Boots + Metallic Accessories ✨

So chic, but SO EASY! Whenever it’s time to dress up and you need an outfit in a pinch, you can ALWAYS rely on this formula! Pair a flowy blouse with structured heels and metallic accessories, and you’re good to go.

This blouse is super underrated. You totally need something like it in your closet. You can wear it with jeans for an effortless outfit like this, and you can pair it with trousers for work. It’s such an easy piece to throw on and INSTANTLY looks good! This one comes in lots of colors, HERE. I’m wearing size S.

➡️ Shop the top (wearing size S)
➡️ Shop the jeans (wearing size 6)

Elevated Outfit With Flare Jeans: Blouse + Pointed Toe Pumps or Boots + Metallic Accessories ✨

Here’s another version of the same formula for a totally different outfit but totally same dressy vibe!

This is one of my favorite blouses for dressing up! The pleated sleeves add drama and elegance, while the fabric at the torso is STRETCHY and comfy! It’s thick, too, so it looks really polished. I own this in several colorways and have worn it to my mom’s 70th birthday, singing for a Christmas Eve service, and singing for Easter. I mean it when I say it’s one of my go-to dressy blouses!

AND, it’s SO affordable, especially during the sales! Comes in several colors, and new colors always pop up through out the year. See them HERE. I’m wearing size S.

These boots have been my go-to dressy style for colder weather for YEARS. They never go out of style, ALWAYS look chic, and make every single one of your outfits look polished with EASE thanks to the pointed toe and sleek heel. (And don’t worry, that heel is skinny but it’s SO easy to walk in because it’s low.)

➡️ Shop the top (wearing size S)
➡️ Shop the jeans (wearing size 6)

Elevated Casual Flare Jeans Outfit: Blouse + Flats or Dressy Boots

With this formula, you can easily create nice casual outfits for day to day. The jeans already feel elevated on their own, and pairing them with a printed or textured blouse and a nice pair of flats or boots keeps the look elevated.

You can do this with any blouse or better-than-basic top. Add pointed toe flats or square toe Mary Janes for polish. You can wear this formula for teaching, casual client meetings, or lunch with friends. Easy, right?

This blouse is a longtime fave that comes out in new prints and colors year round. If you live in a warmer climate, there are some great prints for fall and winter! If you don’t, then consider it for later, when the weather is warmer. It’s such a good top that will work in your closet for a while!

➡️ Shop the top (wearing size S)
➡️ Shop the jeans (wearing size 6)

Elevated Casual Flare Jeans Outfit: Sweater + Boots

Here’s a cold weather outfit with flare jeans for everyday casual activities!

I love how texture on a sweater makes an outfit with sleek, classic flare jeans more interesting and a little more casual and relaxed-looking.

This sweater is super soft and lightweight, but warm and cozy, BTW! I really how relaxed but not-boring it is, thanks to the texture. It is a bit oversized with the drop shoulders and slightly puffed sleeves. It’s a bit trickier to pair with wide leg and straight leg jeans, but it’s seamless with flares because flares hug your figure and create curves to combat the bulk! The sweater comes in several colors.

Also, these boots are my go-to casual boots. The lug sole balances out bulky sweatshirts and thicker sweaters really nicely. Plus, they’re water resistant, so you can wear these any day, rain or shine! I LOVE water resistant shoes because you don’t have to worry about changing your shoes if it rains one day. This colorway is no longer available, but lots of other colors are, HERE.

➡️ Shop the sweater (wearing size S)
➡️ Shop the jeans (wearing size 6)
➡️ Shop the boots (wearing size 9)

Super Casual Flare Jeans Outfit: T-Shirt + Sneakers

Yes — flare jeans totally work for a casual look. You can get tons more wear out of these flares by pairing them with a t-shirt and sneakers!

I went SUPER simple here with a cute graphic print tee and white lifestyle sneakers. But, you can certainly make it more interesting, like adding a cool jacket or colored sneakers. The possibilities are endless, but the formula is the same: a t-shirt and sneakers!

This tee is one of my newest finds. I’m delighted by how the fabric is structured and holds its shape, making it look more polished and refined. It looks way more expensive than it is! Comes in several colors, HERE.

If you’re looking for more tees, I rounded up quite a few below!

This combo is great for errands, school drop-offs, casual Saturdays, kids’ sports activities — anytime you want to feel cute but still comfortable.

➡️ Shop the tee (wearing size S)
➡️ Shop the jeans (wearing size 6)
➡️ Shop nearly identical sneakers

Shop More Graphic Print T-Shirts & Sweatshirts

Super Casual Flare Jeans Outfit: Sweatshirt + Sneakers

Another option is to throw on a sweatshirt, of course!

I shared this sweatshirt in a recent try-on haul. I wanted cropped sweatshirts for pairing with wide leg jeans. It works with flares, too! This sweatshirt is more of a sporty athleisure fabric, so it works great with leggings and athletic pants as well as jeans.

One thing that’s great about flares is that because they hug your hips and taper in a little towards the knees, flares show your figure more and keep you from looking shapeless. Why’s that important? Because it means you can also wear longer sweatshirts with flare jeans and not worry about looking shapeless (like you might if you paired a longer sweatshirt with wide leg jeans).

This sweatshirt is not cropped, unlike the previous one. It’s actually oversized — longer than a regular sweatshirt! Yet, it still looks great with flares because of how flares show off your shape. 🙌🏽

(I told you that certain pieces make looking pulled together effortless. This is a great example of how it just works effortlessly with different pieces!)

➡️ Shop the crop sweatshirt (wearing size S)
➡️ Shop the oversized sweatshirt (wearing size S)
➡️ Shop the jeans (wearing size 6)
➡️ Shop the sneakers (wearing size 8.5)

Flare Jeans Q&A: Fit, Style, and Versatility for Women Over 40

What shoes go best with flare jeans?

You have options! Heeled boots or pumps are great for dressy looks, while flat boots or sneakers work for everyday casual. Just check the length — flare jeans work best when they are about 1/4″ inch off the ground or have a slight break at the shoe for the best look.

For more shoe options, check out my post How to Wear Booties With Different Cuts of Jeans.

What’s the difference between bootcut and flare jeans?

Bootcut jeans tend to be more fitted at the knee and only have a slight flare that fits over boots. True flares tend to have more room at the knees AND a wider opening at the leg. I personally prefer how well flares balance proportions — the wider opening is fantastic at balancing out curvier hips. If you don’t have curves, the more dramatic flare also creates curves really well to give your shape some movement.

Will flare jeans go out of style soon?

Nope! These are 100% classic, so they will always look good. You can pair them with classic pieces to look timeless – an example of that is in the very first outfit I shared here with the dressy blouse and pumps. It’s a timeless outfit void of trends.

Or, you can wear flare jeans with trendier items to make them look trendier.

You basically have a classic, blank slate with flare jeans that you can keep looking timeless or pull it into the trendy zone!

Grab These Jeans While They’re Still In Stock!

These are the flare jeans I reach for again and again, and they will be a workhorse in your wardrobe! You can grab them HERE. They’re often on sale for $31.99, so wait until they drop to that price — or even lower! I wear size 6.

I hope this helps you see how having the right piece makes looking polished SO much easier. And, I hope you feel like you can confidently style outfits with flare jeans on your own with these formulas!

More Outfit Ideas and Fit Tips:

• How to Wear Booties With Different Cuts of Jeans
• How to Look Good In Wide Leg Jeans
• See all of my One Piece Many Ways posts

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