53 Beautiful Holiday Dresses You'll Want To Wear Again & Again

Trench + Longline Coats

Reformation Matteo Trench

Trench coats definitely give you the most coverage, which is perfect for those extra-cold days. More than anything, they supply major main character energy to any look you plan to wear this season. The longline cut brings the drama!

Abercrombie & Fitch Classic Long Trench Coat

This green trench hosts all the classic details: a double-breasted collar, side pockets, and a tie waist. It's timeless as can be, so you can wear it year after year in endless ways.

J.Crew Wrap Trench Coat

If you dare to make a statement, this bold red trench coat is the piece for you. The thick wool-blend fabric will also keep you super snug.

Barn Coats

We The Free Denim Barn Coat

Also called barn jackets or chore coats, barn coats bring a sense of utility to your outfits. They're definitely very trendy at the moment, but I think they're worth wearing past this season alone since you can easily layer up or down depending on the weather.

Reformation Harrison Utility Jacket

Snag a barn coat in a neutral colorway like this, and you've got yourself an absolute wardrobe staple that wears well with any of the colors in your closet. I'd layer this piece up with a sweater, wide leg jeans, and cowboy boots for a chic tomboy-ish look.

1.STATE Oversize Cotton Twill Barn Jacket

This barn coat is intentionally oversized, so it'll be perfect for topping off the multiple layers you've gotta rock for those colder-than-cold days. The sleek buttons and contrasting collar spice this clean-cut style up the perfect amount.

Exaggerated Puffers

The North Face 1996 Retro Nuptse Jacket

When it comes to puffer coats, try taking them a step further by finding styles like this that really emphasize the puffiness. The stitching adds eye-catching textures and patterns that'll supply your outfits with extra oomph. This puffer in particular expertly insulates your body heat with 700 down fill – even snow days are no match for its comfort.

Gap Oversized Denim Puffer Jacket

I've never seen a denim puffer coat before, but now that I've stumbled upon this style from Gap, I need one ASAP. The boxy fit is ideal for piling more layers on, but the silhouette won't entirely drown your figure out.

Free People Solid Cotton Candy Puffer

This "puffy to the max" coat makes a statement with dramatic balloon sleeves and a stand collar that's perfect for cozying up to when the wind chill is just too much.

Leather Bomber Jackets

Wild Fable Faux Leather Oversized Bomber Jacket

Bomber jackets made in a leather (or in this case, faux leather) fabrication feel much more polished and mature than the polyester ones of days past. They toe the line between dressed-up and casual, which is perfect for when you don't want to think too hard about your winter 'fits.

We The Free Buckle Up Vegan Leather Jacket

This pick is perfectly oversized to accomodate more warming garments like sweaters, long sleeve tees, and flannels. Layer up!

Pilcro Oversized Washed Faux-Leather Jacket

This is an undeniable statement coat you can wear on repeat with dresses, skirts, jeans, trousers, and more!

Shaggy + Sherpa Jackets

Mango Jacket with Shearling-Effect Lining

For a fun play on texture, sherpa-lined and shaggy coats are the way to go. This one is also weighted heavy enough that you won't need many extra layers to keep warm while you're out and about!

Sam Edelman Faux Shearling Short Jacket

You'll fall in love with just how soft this coat is. It pairs well with more formal party 'fits as well as casual errand get-ups.

Gap Recycled Faux Fur Coat

No matter what you're wearing underneath, this longline faux fur coat will turn heads. I think it'd look simply iconic with some leather pants and chunky black boots!

As a gal with a little more meat and muscle on her bones, this has always been a problem for me. It’s infuriating, but it feels even more isolating. I can’t always wear the same styles that smaller women do, and even if I do find similar boot designs fashioned for wide calves, they look noticeably cheap or simply don’t check all the boxes in terms of my desired look.

I grew tired of saving all the “perfect” tall boot outfit inspo pics to my Pinterest board only to find that the boots in question had way too small of calf sizes, so I did what I always do when I shop for size-specific pieces: I took to Reddit.

I primarily consulted r/femalefashionadvice, r/plussize, and r/ausfemalefashion to see what people like me are saying about wide calf boots. The frustrations with finding good-looking, comfy tall boots was pretty similar across all three subreddits. As one passionate user put it:

“Even at a size 6, I have never been able to just buy any old pair of boots and have them fit. It is interesting to me how we've made great progress the past several years in regards to body inclusivity, yet somehow there seems to be a huge lack of sizing in regards to tall boots… It makes me so sad to see these beautiful boots everyone else gets to wear, slouchy, over the knee, western inspired, leopard/snake print, etc. Nothing like that comes in wide calf.”

Luckily, Redditors across all three threads suggested a handful of brands that actually offer cute wide calf boots with extended sizing. I had never heard of a few of them, but after scrolling through their sites, it felt like I struck gold.

The top-recommended brands for wide calf boots:

• Penningtons
• Børn
• DuoBoots
• Franco Sarto
• Sam Edelman
• Billini

Franco Sarto Bowman Wide Calf Knee High Boots

You're meaning to tell me these chic boots can really accomodate my calves?! The deep red color already had me sold, but that 15.75-inch calf circumference made this style so much better. They also come in a smooth brown color and a foxy faux-snake pattern, if those speak to your personal style more.

Børn Hayden Extended Calf Boots

The suede leather construction of these boots honestly rivals that of the beloved Campus boot, but their fit is much more roomy, boasting a 16.5-inch calf circumference. These zippered boots also have a playful lace-up detail on the back that's utterly unique.

Penningtons Extra Wide Width Black Tall Heeled Boots with Harness Straps

The calf circumference on these bad boys starts at around 17 inches for shoe size 6, and tops out around 19 inches for shoe size 12. I can't get enough of these moto-style boots and I love that they have the signature harness with silver hardware around the base that other similar boots do.

DuoBoots Saffron Knee High Boots

The fact that you can choose the calf sizing yourself when purchasing these Western-esque boots is ahh-mazing. The options start at 13 inches and go up to 20 inches to hold your beautiful legs without any fuss.

Billini Granger Extended Curve Boots

From all the wide calf boot brands suggested on the Reddit threads I scrolled through, Billini has to be my favorite. They state that these adorable camel-colored boots can fit calf sizes from about 18.11 to 21.42 inches, and while they do have an elastic panel on the sides to stretch even further, I think it's discreet enough that it doesn't distract from the overall look. Score!

Baretraps Thalia Wide Calf Boots

A very similar style to my wishlist Sam Edelman boots, this black pair actually has a 16.5-inch calf circumference that'll fit my legs to a tee. The block heel is the perfect shape and height, plus the toe isn't overly pointed (I don't necessarily care for pointy toes).

Sam Edelman James Wide Calf Western Boots

Finding cowboy boots with wide calves can be a big challenge – but no more! These reddish-brown boots have a 16-inch calf circumference so you can confidently rock any and all Western looks.

Billini Oshea Curve Boots

Immediately yes. These broader-fit boots are everything you need to make a statement with your shoes. They're definitely going on my wishlist! The calf circumferences for this style start at 16 inches and go up to 19 inches based on your shoe size.

Vince Camuto Seshon Extra Wide Calf Boots

With a 18-inch calf circumference, you won't have to worry about squeezing into these tall boots. I adore the timeless squared toe and wide block heel on these!

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!