Olivia Culpo Shows Us Just How Unstuffy a Midi Skirt Can Be

The Katerina Button-Front Dress

My favorite thing about fall is the cozy color palette that comes along with it. This dress' floral pattern is flooded with warm oranges and serene greens that make matching it with your fave cardigans and jackets a total breeze. The v-neckline is universally flattering, too, while the buttoned waist hugs your figure in perfectly.

Maeve Short-Sleeve V-Neck Swing Mini Dress

Another must-have component for any fall dress is comfort. This swing mini keeps things very comfortable, since it's fairly free-flowing against your body. The contrasting stitching along the edges and pockets supply a good amount of structure, though, so you're not totally drowning. This pick would look so chic with a power duo of tall black boots with white socks peeking over the edges.

AFRM Aisla Mesh Midi Dress

For those warmer fall days, this mesh dress saves the day. It surely won't be missed anywhere you wear it, thanks to the bold polka dot pattern. Though bold in pattern, the neutral color palette sets the stage for endless pairing opportunities. This pick has some nice coverage all around the body, plus it arrives ready to wear with a light lining underneath!

Conditions Apply Chloe Maxi Slip Dress

Immediately yes. If you want to stun on your next date night this fall, this slip is the one! The silhouette is simple, but what really makes this piece shine is the swirly stripes of color. The deep jewel tones are fall's perfect fit! This dress comes with removable adjustable straps to let you customize your look, and you can dress it up even further with a chic leather jacket and neutral heels.

PAIGE Kelsee Sleeveless Mini Dress

Along with baggy jeans and denim jackets, I truly haven't been able to escape denim. Fall is *the* time to step out in it! This denim mini dress feels super playful for farmer's market outings or even a low-key day in the park. It has some nice structure to it, thanks to the multitude of pockets and the collared neckline, so it can easily be worn for more formal occasions, too. The tie belt is the real gem of this piece, cinching your figure in in the most flattering way.

Maeve Short-Sleeve Collared Button-Front Knit Mini Dress

This Anthro dress is oh-so retro and oh-so comfy. Its knit fabrication allows it to generously stretch and move with you, never once restricting your figure. The green and white colorway is quite a stylish departure from your expected fall oranges and browns, so your look will most certainly stand out. This mini buttons up all the way, giving you room to experiment with leaving one or two open at the top to perfect your get-up.

Pilcro Short-Sleeve V-Neck Smocked Babydoll Mini Dress

Peter Pan collars are already huge, and they're going to be everywhere once fall is officially in full swing. This plaid babydoll dress takes on the trending neckline with plenty of ruffles, eye-catching stitch work, and puff sleeves for a playful, yet sophisticated effect. It's made to boast a loose fit, so it's a no-brainer when it comes to picking out comfy fall 'fits. I'd absolutely style this pick with cowgirl boots and a knit cardigan to amp up the Western vibes.

The Tobie Button-Front Pleated Shirt Dress by Exquise

Leopard print is another major fall fashion trend for 2024, and there are tons of ways to style it in a polished (not gaudy) way. Case in point is this pleated shirt dress that acts as a statement piece all on its own. The pleats land right around the waistline, stylishly drawing in your figure where you might crave a lil' more definition. The top half of this design is refined by a collar and button-up styling before falling into a flowy midi-length skirt – the perfect pairing for ballet flats!

The Maya Ruched Cowl-Neck Dress: Textured Edition

I'm convinced that chocolate brown looks good on everyone. This Anthropologie dress is a great comfy piece to don for the office or happy hour, since it's high-coverage around the neckline. The leg slit along the side adds a bit of spice to your ensemble, making room for you to show off your go-to fall boots! This pick is stretchy throughout and flaunts a bit of ruching around the midsection to define your bod.

The Cecily Fit & Flare Sweetheart Dress by Maeve

This femme dress fits like a glove. It's undoubtedly vintage inspired, boasting adorable cap sleeves and a sweetheart neckline before falling into a flared skirt. The pattern highlights tons of tiny little raspberries, which will turn heads everywhere you take this piece. The fabric is fairly stretchy while still providing some structure to your look. For fall, wear it with a denim jacket and white sneakers for a no-fail casual-but-cute outfit.

The Fleur Strapless Maxi Slip Dress: Linen Edition

Everyone needs a reliable (and high-quality) black maxi. This linen pick is very straightforward in design, boasting a strapless look that'll look iconic with any fall layers you already have in your closet. From denim jackets to colorful cardis, this Anthro dress is a total wardrobe staple to pair with your faves.

Damson Madder Dion Leopard Carpenter Cargo Pants

Leopard print jeans are perhaps the lowest-risk way to try out the pattern, especially with this subdued pair. Where some leopard print pieces really boast the pattern with bright colors and high contrast, these are less flashy, but still noticeable. They flaunt a high-rise fit and wide cargo pant legs. I'd style these with a fitted black top and black ballet flats to tie the look together.

Reformation Bella Skirt

I fell victim to the great leopard print midi skirt trend back in 2019, and this piece definitely reminds me of its more mature, grown-up sister. This maxi-length skirt from Reformation falls all the way down to the floor, providing a very sleek and chic feel to your silhouette. It's a great contender for a 'night out' outfit – I'd wear it with simple kitten heels and a tiny tank to really up the pattern.

Dolce Vita Notice Stitch Sneakers

Not ready to rock full-on leopard print? Opt for some stylish sneakers like this pair from Dolce Vita. They boast the same sporty flair as the famed Adidas Sambas, but certainly have a bit more personality, thanks to the mixed materials and playful stitching. I'd wear these with some black wide-leg jeans and an oversized graphic tee to give real cool girl energy.

Mango Leopard Knit Cardigan

This leopard printed sweater is everything, and not just because of the foxy pattern. I think the clean-cut hems and slightly-cropped sleeve length really play up the spots in an elevated way, plus you can fuss around with the front buttons to find your utmost perfect fit. Wear this baby with some black capris and kitten heels to achieve a super chic model off-duty look.

A New Day One Shoulder Midi Dress

For an easy one-and-done, this midi dress is the way to go. It's made to have a bodycon fit, so it'll flatter your figure perfectly. As opposed to your basic slip dress, this one flaunts a fun one-shoulder shape with a bow tie at the top. Plus, you get a little bit of sexy edge from the leg slit on the side. A true statement piece! I think it'd look divine with dark red ballet flats and a lightweight black cardigan that you can leave on or easily take off, weather permitting.

Damson Madder Lily Carpenter Mini Skirt

Another denim leopard print iteration – I simply love to see it. Mini skirts are the most versatile garment you can keep in your closet cross-seasonally, since they look great styled with sandals and winter boots alike. This printed one boasts ample pocket space and an ideal length for sophisticated and casual moments alike. For fall, I'd style this skirt with tall riding boots, tights, and a crisp white button-up shirt to channel an office-ready 'fit.

Dolce Vita Silvie Shoulder Bag

The best part about this leopard print purse is that it's reversible – one side is covered in spots, and the other is solid black. This two-toned quality can come in super handy on days you don't necessarily want to wear all-out leopard. The print won't be the only thing turning heads, though. This bag is fitted with both silver and gold hardware as well as an asymmetrical body shape to make your look stand out from the rest. Since it's so bold, I'd definitely pair this piece with a classic little black dress or just jeans and a white tee to let the bag speak for itself.

Sézane Betty Cardigan

This Merino wool cardi mimics a jacket, but feels insanely soft. The collar, front pockets, and buttons polish the look up superbly. You could easily wear this pick alone or layered on top of a basic tank. I think it'd look so chic alongside some dark-wash wide-leg jeans and platform sneakers.

Gap Leopard Belt

For a small touch of leopard, this sturdy belt from Gap does the trick. It's an unexpected pop of pattern that'll work well against a monochromatic all-black 'fit.

Ganni Leopard Cotton Poplin Peplum Tie Blouse

There are so many iterations of this tie-together blouse out there, but Ganni truly did it first. They've certainly hopped on the leopard print trend with this piece that's all about flowy-ness. The puff sleeves, roomy round collar, and peplum silhouette make for an uber-comfy wear. I'd pair this top with black barrel jeans to shape the look even more, then finish everything off with some eye-catching sneakers.

Zara Animal Print Tulle Halter Dress

This halter dress has a sultry plunging neckline and an open back, so it's definitely the best fit for cocktail hour or a late-night party. The leopard print has some variation throughout the fabric, so it doesn't feel too repetitive or cheapy. I think some sleek heels and plenty of gold jewelry would work amazingly well with this piece.

1. Talking About Money Can Expose Hidden Feelings

It's impossible to know how someone feels every second of the day, but we probably all think we have a good understanding of the people we're close to. But people are capable of hiding how they feel about something or burying their discomfort until certain situations 'expose' them. Why does it seem like money has a way of doing this?

Both Irwin and Dunlap agree that "money is taboo," leading people to avoid conversations about it. "Data tells us that we are more likely to talk about any other taboo topic—sex, politics, religion, even death—before we’ll talk about money," says Dunlap. West agrees and says, "Money is like that one friend who’s incredibly helpful but totally untrustworthy—everyone likes what they bring to the table, but no one wants to talk about them directly." Did you think of someone specific? It's okay because I did too!

The problem is that money can make "hidden insecurities come out, old sibling rivalries rear their heads," and more, according to West. "Even something like 'who paid for what' can suddenly become a life-or death conversation," she says. It's strange because Irwin says a Wells Fargo study shows that "many Americans across all ages are worried about money," proving we're all thinking about it, despite our avoidance issues.

2. And Money Can Also Create Unease In Conversations

"When we don’t have open conversations about money, we’re left to navigate it on our own, which can keep us feeling underpaid, overworked, or unsure about our financial situation," Dunlap points out. She feels "discussing money requires a huge amount of vulnerability" which "isn't easy for everyone." You may have seen how other topics are swept under the rug by family members or friends based on reasons they're not ready to talk about.

Though Irwin believes saying something like saying, "'Here's what's keeping me up at night' or 'here's what my goals are' could strengthen connections," Dunlap knows that "shame, comparison, or fear of judgement" can cause people to remain tight-lipped about their finances.

If you've experienced a weird moment because of money or had to be the unfortunate witness of an awkward conversation, my apologies. It's not fun no matter who's involved because, unfortunately, "money carries layers of emotions, like pride and insecurity, that turn simple conversations into potential minefields," says West.

Dunlap says there's a silver lining if people are willing to be open, however. "The key is respecting each person’s comfort level, and encouraging openness if they're willing to meet you there. It’s not going to be perfect at first, but by starting to share more about your own financial experiences, you can start to break the cycle of shame and fear around money. You might be surprised at how quickly others are willing to open up too."

3. Making Assumptions About Other’s Money Status And Financial Situation Can Lead To Disrespecting Boundaries

No one's saying you should never lend friends money, but being mindful about the decision is worth noting. West feels "it's complicated" while Dunlap believes the issue "can be tricky." There's a chance a low-key loan becomes an expectation that you should dish out money every time someone needs help, even if you're trying to maintain your own bills. "Lending money to a friend is like sharing your Netflix password—simple in theory, but one wrong move, and things get weird," West forewarns.

Dunlap also says, "When you lend money to someone close to you, there's always the chance that you won’t get it back. You want to be mentally prepared for that! Otherwise, it can strain your finances and your relationship. The emotional toll can be just as heavy, as unpaid loans can lead to resentment or awkwardness." It's not unusual to hear about certain friends being unreliable in more ways than one after you've let them borrow something. Unfortunately, Irwin indicates this happens because some people "don't expect to give something back that they've borrowed."

Because of this, Dunlap thinks "it's best to avoid loans if possible." Should you decide to move forward with helping out a friend who's in a bind, make sure you're both in agreement about repayment and what to expect moving forward. West says "having clear terms" or "gifting a small amount if you can afford it" is like "buying their friendship insurance." The latter is something Dunlap agrees with because it "helps prevent resentment if they can't pay you back as planned." Plus, she feels it also "keeps the loan within an amount you're okay with potentially losing."

4. Lending Money Is A Slippery Slope That Can Lead To Distrust And Resentment

It's amazing how money can lead to a friendship breakup if boundaries aren't created or respected. "Money is a sneaky little devil who can push everyone’s buttons. It can cause resentment if one person feels taken advantage of or someone’s 'casual loan' becomes an epic saga of unpaid IOUs," West says. Not only that, but Dunlap knows "money can strain relationships between friends and family by highlighting differences in how we value it, expect to use it, or feel about sharing it."

Friends and family members shouldn't take each other's kindness for granted, but human nature is fickle at times. That's not an indicator that someone you love is a "bad" person, but they may feel like you owe them your time and money. However, Irwin says this isn't "de facto that that person is entitled." Still, Dunlap is more than aware how this can play out. "For example, it can lead to resentment if one person is always the one picking up the tab, while another might feel uncomfortable or indebted because they’ve been helped financially," she says.

On the other hand, it can show up a little differently in families. She adds, "Issues like unequal inheritance or constant requests for financial help can lead to deep emotional tension. Money can also become a tool for power imbalances, where one person feels in control and the other feels dependent, and that can mess with trust and respect."

When certain negative patterns show up in relationships, it can make people decide to take a step back from being available. "And once distrust settles in, it’s hard to shake; nobody wants to be 'that friend' who’s forever dodging a Venmo request or getting side-eye from relatives at every family BBQ," West points out. How many times have you built up a wall with the people you love because of repeated unreliability or the expectation that you're supposed to help them whenever they ask? If you didn't hesitate to think of a moment, you're living proof that distrust can affect even the closest relationships.

Dunlap says, "When money becomes a main factor in a relationship, it can overshadow the connection, making it difficult to maintain genuine trust and understanding. You can avoid this by having open conversations with friends and family about your financial situation. Clear communication can help keep the focus on the relationship, not the money."

5. You Can Worry You're Not A Good Friend Or Family Member For Setting Money Boundaries

Worrying about how other people feel can keep us from setting boundaries. There's a difference between being an empath and a people pleaser, but it's easy to blur the lines. You can absolutely empathize with someone's hardship while knowing you're not in the position to lend the amount they may be looking for. I'm a huge fan of saying that two things can be true at once — because they can.

Irwin says you need to "address the conversation head on" if a friend does ask you for a loan. Your response may depend on if their ask was "emotionally-charged or "in an uncomfortable environment," but Irwin doesn't recommend ignoring it. If you're not in the space to respond, here's what she suggests saying in a "timely" fashion:

1. "Hey, I need time to think about this. Let me get back to you."
2. "We can help you, but here are our boundaries."
3. "We see and understand you, but we're unable to help because we're trying to pay off debt or save for _______."

Yes, Financial Boundaries Are Essential

Don't think you need to create financial boundaries for yourself and your friends? Think again. West says, "Establishing some ground rules is a lifesaver—think of it adding airbags to the friendship. Setting boundaries early on, like when you’re still in the happy, non-monetary part of the relationship, can protect both sides if things get sticky."

Here's how she advises you proceed with creating boundaries:

1. Keep it light and be honest; you’re not making a prenuptial agreement here, just letting them know you’d like to avoid “financial fireworks” later.
2. Say, “I’m your friend, not your ATM.” It’s funny but helps set the tone that your wallet isn’t a free-for-all.
3. Set a gift cap, such as, "I'm happy to chip in for brunch or a birthday, but let’s not get into home-loan territory.”
4. If you do lend, draw up a repayment plan. Think of it as adulting with a side of accountability to avoid “accidentally” becoming their financial fairy godmother.
5. Limit talk of big financial choices unless you’re genuinely invested together. After all, nobody needs to know how much their friend spends on avocado toast or scented candles, let alone home renos.
6. A little humor and some boundaries go a long way. You’ll save yourself a lot of awkwardness and keep the friendships intact, one “non-loaned” dollar at a time!

Tori says, "It's so important to have transparent conversations about money, set clear boundaries, and ensure that relationships are prioritized in any money exchange." Here are a few things you can try:

1. Communicate about your budget with a “gratitude sandwich.” Say you’re invited to an outing—a dinner, or a sports game—that isn’t within your budget right now. You can respond with the “gratitude sandwich.” The “pieces of bread” are positive, and the “meat” is the money thing you’re scared to say. Thank that person for the invite, let them know it’s not within budget right now, and then offer a cheaper alternative, reassuring them that you’d really love to see them. Offering an alternative reminds that person that declining their invitation isn’t about them, and you still care about them. In doing so, you prioritize your budget AND your relationship in the process.When in doubt, remember that no is a complete sentence. You don’t need to overcomplicate things, and sometimes a simple “no” is all you need.
2. Set expectations early. When planning trips with friends, discuss the budget and how costs will be split upfront. Having these conversations ensures that everyone is on the same page and helps avoid any misunderstandings. It creates a supportive, stress-free environment where everyone can enjoy the experience together without any added worries!

The Final Verdict:

Once you've weighed your options and considered what you need, you can decide to loan your friend money. However, Irwin wants you to consider being formal about it. "You can absolutely draft a promissory note or loan agreement so that your friend knows how serious you are about your boundaries. If you want, you can also put an interest rate on it," she says.

It's not to hurt your friend's feelings, but it is a boundary you can put in place so they think to themselves, "This is truly a loan because I'm borrowing money with the intent to pay it back," Irwin says. It could change the dynamics of your friendship, but it's more about being "purposeful about the language being used" so you and your friend can both move in the "right direction," according to Irwin.

If the idea of creating a 'loan agreement' sounds icky to you, Dunlap wants you to seriously consider it as "an extra bit of protection." She says all you need to do, again, is "try setting up a simple contract to outline repayment terms" because it "can help both of you stay on the same page and avoid misunderstandings down the road."

Her ultimate piece of advice? "Only lend what you're comfortable giving and potentially losing, and keep open communication to maintain trust and respect in the relationship."