12 Celeb-Approved Ways to Wear a Pencil Skirt

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.

When's the best time to do holiday shopping?

The best time to do holiday shopping really all depends on your personal shopping goals. Do you want to get a jump on items you know will sell out soon? Do you want to save the most money possible? Do you want to focus on handmade, personalized gifts? These factors will undoubtedly influence your holiday shopping schedule.

Shopping early can be advantageous for all of the aforementioned goals. A lot of retailers start promoting their holiday products early on, giving you ample time to snatch up that limited-time lip kit or fancy water bottle you’ve been eyeing way before the holidays.

Plus, some of the best deals for holiday shopping happen ahead of Black Friday and Cyber Monday – in 2023, Experian observed a surge in early spending in October, thanks to early discounts, a trend likely to continue in 2024.

Finally, shopping early can be especially helpful if your plan is to focus on handmade or personalized gifts, giving the artisan you buy from (or yourself, if you’re DIY-ing your gifts) plenty of time to craft the item with love and care.

Gallup reported in 2023 that one in four shoppers start shopping as early as September, a trend likely to continue in 2024 – so you might already be embarking on your shopping spree!

If right now is just still too darn early for you to start holiday shopping, Black Friday and Cyber Monday are some of the best times to shop since so many retailers offer their largest discounts of the entire year. Plus, the late November-early December timeline can feel a bit more appropriate for the gifting season opposed to late October-early November, when everyone’s still recovering from Halloween.

The only thing to consider during this time is the shipping timelines for the items you purchase – but most retailers will typically advise their specific shipping schedules, so you don’t risk your goodies arriving late.

Where should I shop for gifts?

You have three main options when it comes to where to shop for holiday gifts: online, in-store, and via our amazing gift guides. Of course, each method has its advantages and disadvantages.

Shopping in-store offers a tangible experience: the opportunity to hold specific items in your hands and gauge exactly what they’ll be like when you give them as a gift. The pitfall with shopping in-person is that it typically requires a commute and journeys through potentially very busy malls and shopping strips, which can add to the already-stressful holiday experience.

In-store shopping can be more physically exhausting, but it’s all about preference! Sometimes strolling through the stores that get all dolled up for Christmas is the best part of the season.

Per Google, 65% of those planning to shop for the holidays say they will shop online more. Shopping for gifts online can be super helpful since you can centralize your findings in your browser’s bookmark tab or via virtual cart(s). Plus, shopping online can pose more opportunities for saving some money: lots of retailers typically offer discount codes for online users, especially if you sign up for their digital marketing channels (like email and text) and make a purchase.

Shopping online isn’t just shopping, either. The internet can be a stellar research tool to help you vet whether certain products are worth it, where they can be bought, and when they’ll be available. In fact, Google reported that more than half of U.S. holiday shoppers who went into a store last year say they looked up product reviews online and/or located an item in-store by checking it online.

Last but not least, scrolling gift guides has to be our favorite place to shop for gifts – and not just because we write and publish them.

At their very core, gift guides help streamline the holiday shopping process, alleviating the stress that bubbles up when you’re wondering what the heck to shop for in the first place. Our gift guides are backed by real people, real experiences, and real opinions from our editorial team. We only promote products that we really love and believe in, oftentimes ones we’ve tested and reviewed ourselves.

We have gift guides for just about everyone on your list, with more on the way! Check ‘em out:

• Gifts for Him
• Gifts for Her
• Gifts for Foodies
• DIY + Handmade Gifts
• White Elephant Gifts
• Gift Sets

What are the best kinds of gifts to give?

The best kinds of gifts to give are thoughtful gifts that consider the giftee’s interests, wants, and needs. These gifts can be sentimental, practical, or both simultaneously. What matters most in a gift is that it’ll be meaningful to them past just the holiday season, whether it’s helping them get through daily tasks, reminding them of a memorable trip or event, or giving them small doses of joy.

“Shoppers are increasingly looking for personalized and unique gifts that reflect the recipient's personality and interests,” says Mia Anderson, Owner of ChicSew. “With the rise of online shopping, many consumers are opting for curated gift boxes or experiences that add a special touch.”

Gift boxes, personalized items, books of interest, self-care goodies, and even gift cards can all be thoughtful gifts depending on the recipient. If you have no clue what your giftee is into, it’s not a bad idea to ask them what they want the most!

“My idea of a great gift is something that is in tandem with the recipient's interest and offers something new to the person, be it learning a new skill, enjoying a calming activity, or simply spending quality time with the family,” says Alfred Christ, Sales Manager & Marketer at Robotime. “This season, we encourage shoppers to shift their focus on quality and the memories their gifts will create and not just merely material aspects.”

When is Black Friday?

Black Friday is always the Friday after Thanksgiving. This year, Black Friday lands on November 29.

When is Cyber Monday?

Cyber Monday is typcally the Monday after Thanksgiving. This year, Cyber Monday will land on December 2. Oftentimes, retailers and brands extend their online offers through the week (coined Cyber Week) after the event. Salesforce reported that 67% of shoppers in 2024 plan on shopping during Cyber Week!