5 Comfortable Fall Outfits to Invest in Now

Tommy Hilfiger Crossover-Hem Dress

Florals for spring aren't groundbreaking, but during fall they are. This crossover-hem dress is for anyone who's been reading one too many dark romance books and want to dress like the mysterious book or tea shop owner who's stylish. It has an invisible back zipper for a seamless look and is lined in case you're afraid of wearing something sheer.

Avec Les Filles Faux Leather Drop-Waist Dress

It's hard to believe, but leather dresses can be sexy without revealing a lot of skin. The bodice is fitted, but the 'skirt' portion flares out, offering a nice balance that makes you feel comfortable. Plus, we just love a drop waist!

Lauren Ralph Lauren Double-Faced Georgette Shirtdress

It's Ralph Lauren — of course you'll want to wear this shirtdress every other week! This design is incredibly flattering, and it's the perfect shade of green to rock this autumn. Okay, and the cute barrel cuffs are also a nice touch!

Vince Camuto Floral Printed Faux-Wrap Belted Dress

Add pops of flirty color to your fall wardrobe with Vince Camuto's belted dress! The ruffled hem will make it look like you're wearing floating flowers which will look so good with a pair of Steve Madden boots! The belt camouflaged against the dress, so it almost looks like there's nothing there — perfect for anyone who can't be bothered to tie the perfect bow.

Petal and Pup Callum Dress

Denim dresses are still trending which is why this Petal and Pup piece is a must-buy for me. From the classic neckline to the accented stitching, it's a pick you'll want to wear over and over.

Donna Karen Faux Leather Side Ruched Dress

Unafraid to show a little thigh while wearing faux leather? Get into this Donna Karen dress — literally. You'll love the side ruched detail along with the neckline meant to accentuate your chosen necklace. It'll hug your curves in all the right place without making you feel like you're stuffing yourself into something that reminds you of a moto jacket.

DKNY Ombré Belted Pleat Skirt Dress

You can easily get away with wearing this pleat skirt dress to work or church because the hemline rests right below your knees. The cute contrast between the solid top and pinstriped bottom keeps it from being anything but boring which is the goal for fall.

24seven Comfort Apparel Collared Wrap Dress

Dressing for comfort is at the top of everyone's list this fall, so it makes sense to have a collared wrap dress on-hand this season. It's the easiest way to look sophisticated without trying too hard. All you'll need are a pair of cute Target heels, cute jewelry, and one of your wool fall coats to complete your look.

En Saison Mixed Media Dress

You have to buy at least one cute ribbed dress during fall — it's an essential piece that signals the transitional weather. Though the temps can fluctuate depending on where you live, you can definitely get away with wearing this dress once temperatures drop down to 65 degrees and or lower!

ELOQUII Plus Size Funnel Neck Dress

This easy fit dress was made for fall! You don't have to worry about pesky zippers because you just simply pull it over your head and it glides right over your curves. It does have a funnel neckline, but the fabric will accentuate your hips in the best way.

Donna Karan Metallic Brocade Dress

Have a birthday or special event coming up? Don't get caught lacking without this metallic brocade dress! It reminds of The Gilded Age with it's gold pattern that's set against organza.

Short Steve Madden Boots

Roland Brown Leather Boots

Every fall closet needs at least one pair of Steve Madden boots that are a little rugged. These are great for the days when it's rainy out and you're not trying to chance slipping on the pavement.

Put on your best trench coat, rib knit sweater, and boot cut jeans for a casual look you'll replicate well past winter!

Lizabelle Leopard Boots

The leopard print trend is the gift that keeps on giving because it seems to refresh itself every year. It seems like everyone can agree it's one trend you can't mess up. The sleek design and squared heel give it an air of chicness that makes it look like you're ready to take on the Runway office á la The Devil Wears Prada.

Rogue Black Box Leather Boots

Feeling drawn to dark academia books now that it's fall? We don't blame you, but we do suggest slipping into these Rogue Black Box leather boots! We can see someone from the cast of The Chilling Adventures of Sabrina wearing them with something preppy.

Keeper Black Leather Boots

More concerned with walking to the beat of your own drum than keeping up with trends? You'll love these comfortable moto boots. While these don't come in half sizes — so you'll have to size up if you're more of a 7.5 than a 7 — they're still the perfect match for all the cute leather jackets we can't stop looking at!

Brooks Beige Snake Boots

Going for a rocker vibe this fall and need something that'll make you stand out in the crowd? Go for these snake print ankle booties! They're the pointy best friends to the faux leather pants you'll be shuffling into. Who knows, you might keep them in heavy rotation with all of your fall outfits.

Crue Chestnut Boots

You don't have to go over budget to wear UGGs — these dupes to give you the same appeal and comfort for much less. The inner lining is made of cozy faux shearling which will work with those days you'd rather be bed-rotting, but are forced to show your face at school or to run a few errands.

Avalanche Tan Boots

Plan to spend a week at a semi-secluded log cabin? This pair is very aptly named 'Avalanche' for all your outdoor adventures. They're cute, functional, and will keep your feet warm when the temperature drops.

Long Steve Madden Boots

Dawn Wine Boots

These tall boots are the exact shade of wine red everyone's going crazy over this fall! No really, you need Dawn — yes, I'm on a first-name basis with these boots — because she's going to elevate your sweater dress. Although the picture shows otherwise, the heel on these boots are more comfortable than you think.

Lasso Brown Distressed Boots

We've seen a lot of cowgirl boots during the past couple of years, but none are quite as sexy as this pair. Keeping on par with the distressed look, we're sure the stitching also plays a role in what makes them unique.

Since each pair of these boots are handmade, it's normal if you buy a pair that doesn't look exactly like this. You'll still be getting the same premium leather and sexy wear these boots promise to give.

Baddie Brown Distressed Boots

These pair of distressed Steve Madden boots are like a foray into that rebellious part of ourselves we generally keep locked away. While we're not talking about anything too crazy, we are talking about our inner rebels who have finally learned to stop being people pleasers.

It's no coincidence these are appropriately named 'Baddie.' Let yours out and grab this pair!

Lucid Brown Suede Brown Boots

If you plan to spend time in printed maxi dresses, you need these suede boots. If you're giving them the side eye because they have a kitten heel, but we say don't knock it until you try it! Every outfit doesn't have require 4+ inch heels, especially if you plan to spend time visiting an apple orchard before heading over to a pumpkin patch!

Lizette Cognac Suede Boots

There's the squared-heel we've fallen so in love with! While traditional stiletto heels are usually praised, we think nothing beats it's sleeker (and more supportive) sister. When that heel is paired with suede, you get these perfect Steve Madden boots.

Lander Black Crocodile Boots

The best thing about crocodile print boots is how well they elevate any outfit. From casual to date night outfits, the Lander Boots will make you look sophisticated with every step you take. Don't be surprised if people keep stopping to ask you where you got them from.

Bellamie Sand Suede Boots

Is it the year of the suede boots? We won't go as far as to say that, but it seems like our favorite Steve Madden boots have this one feature in common. The slouchy appearance will still give your outfits a touch of elegance, but people will know you're approachable given the relaxed fit.

Ruskin Chestnut Suede Boots

Take a break from anything with a heel height over 2" and go for the Ruskin boots. They have a squared-toe that'll make people think twice about messing with you in public. They have the perfect weather-beaten look that makes certain boots look better over time which adds to the appeal of them.

Faye Bone Leather Boots

If you could care less about looking approachable, slide your feet into these bone leather boots. They're trendy and look like they mean business — like all your upcoming fall outfits.

Ex-Husband Jonny Lee Miller

Angelina Jolie and Jonny Lee Miller entered each other's orbit during the filming of Hackers. This 1995 movie has everything to do with it's name, and ends with said Hackers ultimately unraveling a greater conspiracy. As is sometimes inevitable, Jonny and Angelina got close throughout filming, but went their separate ways once their time on set ended (via US Weekly).

They didn't stay apart for too long because they eventually got married the following year. It's even reported that Angelina proudly made a dark statement during their small wedding by wearing a t-shirt with Jonny's bloodied name written on it. She didn't do it to be gross though, but wanted to solidify their vows. "You’re about to marry him. You can sacrifice a little to make it really special," she remembers telling herself (via The New York Times). But, their marriage dissolved in less than two years and they decided to get divorced in 1999, according to US Weekly.

The two would go on to be amicable with each other, with Angelina even referring to Jonny as a "great friend" (via US Weekly). Earlier this year, Jonny sat down with Johnny Vaughan of Radio X to reveal something shocking. "I jumped out of an airplane...I was dating a young lady called Angelina," he said. He then shared that it was Angelina who encouraged him to do this daredevil feat with her. "She is cool as a cucumber. Fearless, that woman."

Ex-Girlfriend Jenny Shimizu

During the brief time Jonny Lee Miller and Angelina weren't communicating, the Maria actress entered her first relationship with a woman. Jenny Shimizu and Angelina co-starred in another mid-'90s movie called Foxfire that centered the lives of teens and the bad decisions that land them in precarious situations.

Recounting how she felt about Jenny Shimizu, Angelia told Girlfriends magazine, "I fell in love with her the first second I saw her. Actually, I saw when she was being cast in Foxfire, and I thought she had just read for my part," she said. Ironically, her future ex-husband Brad Pitt was mentioned in the same interview, but the two hadn't met yet.

There's not much info about Angelina and Jenny's relationship beyond this, so it seems like things didn't last long.

Ex-Husband Billy Bob Thornton

Here's where Angelina's relationships truly started to getting interesting. After things ended with Jonny Lee Miller and Jenny Shimizu, her next partner was none other than Billy Bob Thornton. InStyle recalls the two co-starred in Pushing Tin together, a movie about the ins and outs of two co-workers' fraught romantic relationships. Given the movie released in 1999, everyone didn't know how to respond to Angelina and Billy Bob's marriage the next year.

Unfortunately, even Laura Dern was caught by surprise — she and Billy Bob were allegedly engaged at the time. "I left our home to work on a movie, and while I was away, my boyfriend got married, and I’ve never heard from him again," she said, according to ABC News. That's...not the way to go about things, but apparently Angelina and her new husband didn't care at the time.

From then on out, Angelina and Billy Bob frequented red carpet events together. They didn't shy away from pulling off, uh, interesting stunts, that left everyone speechless. No one will ever forget when Billy Bob unashamedly admitted the two got frisky before walking the red carpet at the premiere of Gone in 60 Seconds.

However, their marriage dissolved because of their "different lifestyles," according to Billy Bob (via E! News). "So, that's really — that's the only reason we're probably not still together, maybe, because of a different path in life we wanted to take," he said.

Ex-Husband Brad Pitt

This divorce breaks our hearts to revisit, but here we go! Everyone knows Brad and Angelina starred in the hit movie Mr. & Mrs. Smith, but we also could tell their intense chemistry had nothing to do with playing their respective roles. These two had such sizzling energy onscreen that it didn't take long for people to speculate Angelina was the reason Brad decided to part ways with Jennifer Aniston.

However, Angelina reportedly denies that was the case. She did notice she and Brad were excited to see each other at work though. "Because of the film, we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened," she said (via PEOPLE). According to the same outlet, it didn't take long for Brad and Angelina to move forward with their feelings once it was clear Jennifer was going to be out of the picture.

Though Brad and Angelina expanded their brood to include six children — Maddox, Pax, Zahara, Shiloh, Knox, and Vivienne — a terrible incident unraveled everything. According to the BBC, Angelina accused Brad of become a belligerent drunk during a flight that resulted in injuries. She didn't waste time filing for divorce, which spoke volumes to us.

Um, The Weeknd?

Much to our surprise, Angelina Jolie and The Weeknd were rumored to be getting close around two years ago. They were seen on several 'dates,' one being at Giorgi Baldi, which continued to make people believe they were secretly dating (via Daily Mail). Since neither confirmed or denied the nature of their relationship, it's hard to say if there's any merit to the rumors.

We'll just have to speculate and keep it moving!

Is Angelina Jolie dating anyone these days? 

Last year, Angelina spoke with WSJ Magazine to talk about about her life and career. She intimately revealed that her body reacted to all the pressure from going through her divorce from Brad which serves as a stark reminder why stress is never good for anyone! "I suddenly had Bell’s palsy six months before my divorce," she shockingly admitted. She also made it clear her focus was on her kids and nothing else. "They are the closest people to me and my life, and they’re my close friends."

Despite being recently linked to British rapper Akala, Angelina put an end to rumors they're dating today. A source said, "They all work together," referring to Akala's relationship with someone else. "Angelina remains focused on her family and is not dating at this time," (via PEOPLE).