We’ve officially hit December, and freezing temperatures are approaching. As retailers push out their new seasonal and holiday-ready items, there’s a plethora of pieces to sift through, from chunky knits to glittery pieces galore. I figured you might need assistance sorting through the shopping void, so I spent a few hours finding the best picks amongst the seemingly endless pages. Looking for a cozy sweater that checks all your boxes? I’ve got you covered. Hitting a wall when it comes to getting dressed and need a little wardrobe refresh? Check! Desperate for an affordable and festive dress for your next party? You’ve come to the right place. Did I also mention that everything in this roundup is under $99?
Regardless of what you’re looking for, I’ve got 99 products priced under $99 for you to peruse, and all are editor-approved and curated for the season ahead. I couldn’t help but share some of my finds with my fellow editors during my search, and they were quick to click the add-to-cart button, FYI. I’ll keep this short because I don’t want to keep you from the finds below. Keep scrolling to get started shopping these picks before they inevitably sell out.
While these may not be the most weather-appropriate shoes—there’s nothing like a pair of tights can’t fix.
Scarf coats can come at a pretty hefty price point, so you can expect my joy when I found this under-$100 option at Zara.
Studs can easily be construed as tacky if not done right, but the design team at Mango knew exactly what they were doing.
With a sleek skirt like this in your wardrobe, you’ll be your office’s best-dressed employee.
I haven’t looked at Old Navy in years, but when some of my favorite fashion follows pointed out that this casual cardigan was a worth-it easy buy, my interest was piqued.
Here’s to bringing #ArmCandy back in 2024. Start with a chunky cuff like this, and opt for layering with other daintier bracelets.
I’m thoroughly impressed by Madewell right now.
These shoes are a work of art.
Instead of dealing with straps falling off your coat’s shoulders this winter, opt for a chic crossbody bag like this so you can travel with ease.
Cashmere lined and red paneling? Say no more.
These earrings will make any outfit feel a bit more special.
To the average eye, this may look like a regular scarf with contrast stitching. But to the fashion eye, it’s giving a touch of Toteme.
Holiday party ready.
A $60 blazer that’s giving $500 energy.
If you’ve been on the lookout for an affordable leather bomber jacket, look no further.
Mesmerizing.
Ever since the David Beckham documentary came out on Netflix, I can’t stop looking through Victoria Beckham’s quintessential WAG outfits. I’ll be buying these red track pants and pretending I’m rooting for my husband on Manchester United.
The teeny little bows!
I’m shocked that these aren’t sold out yet.
My best J.Crew finds have usually been found on sale. At 50%, this is hitting the jackpot.
This top’s almost $30 cheaper on Shopbop then it is on Pixie Market’s site. (Plus, Shopbop has 2-day shipping!)
I haven’t met a metallic shoe that I haven’t fallen in love with, but I’m really swooning over this pair.
The matching skirt looks just as good.
I’m not sure what I love more, the subtle hairy texture or the beautiful butter yellow color.
Like all of Topshop’s other maxi and midi skirts, I predict this one will also sell fast.
This is exactly the kind of fresh denim shirt that my closet is missing.
If you’re like me and always reach for the trusty black boots, try switching things up with a brown or tan pair this season.
Isn’t this just one of the prettiest dresses you’ve seen?
With Sheertex’s durable technology, these won’t be the tights that rip after only one or two wears.
The last time I put these luxe-looking drop earrings in a story, they sold out within a few days. Just a heads up!
Dazzling!
Don’t let your layers keep you from accessorizing this season. Even under a coat, this necklace exudes luxury.
Adorable.
I’ll always swoon for a ’90s-inspired item.
Take a closer look—the buttons are what really sold me on this top.
I recently did a story on Meghan Markle’s style in Suits, and this skirt is very Rachel Zane-esque.
Winter is here—it’s time to be fully prepared, and do it in style.
Trust me, everyone at the holiday party will be asking you where this top is from.
Polished and cozy.
I don’t see the widespread love of Mary Jane flats going away anytime soon. (Even if it does, I’ll still be wearing mine!)
If The Row’s bucket bag is exceedingly out of your budget, take a look at this Zara pick.
If you want to have a little fun with your wardrobe but aren’t drawn to overly statement pieces, opt for a basic that has a simple design change, like the asymmetric waist here.
A striped sweater may be considered a “boring” wardrobe item, but it’ll be one of the most worn items you’ll own.
I bought these after being inspired by the mesh shoes I saw in Proenza Schouler’s recent runway collection. I have to say, I was just impressed with the shoes IRL.
Instead of pumps, try pairing this skirt with a pair of kitten-heeled slingbacks.
In case you can’t tell, there are quite a few wonderful holiday party dresses in this roundup. I just want you to be prepared, no matter what your festivities look like.
And if you have that holiday dress already secured, earrings like this will be the special touch it needs to finish the look.
To make the classic Canadian tuxedo more interesting, opt for different shades of denim.
See the note above.
COS’s giant quilted bags are a fan favorite, and I think people will feel the same about their hat version.
How fun are these?
What a steal.
If you tell people this skirt is from Zara, they’ll be shocked. (I was when I first saw it.)
Available in seven different shades and spacious to fit anything you’d need.
Made from a blend of alpaca and merino wool, this will definitely keep you warm.
The ultimate layering top.
Just look at that sheen!
No such thing as too many striped sweaters.
Barrel-leg jeans are *the* denim trend right now, and this specific pair is a Who What Wear editor favorite.
The selection of Mango on Nordstrom right now is exceptionally good. Find all your wardrobe needs in one place, including this fun little bolero set.
Ever since Miu Miu included hoodies as a part of its F/W 23 collection, I’ve been itching to emulate the ultra-cool look. This jacket will be my starting point.
Why shell out hundreds of dollars when you can find sunglasses that look this cool for only $39?
I’ve seen this top included in dozens of Who What Wear stories—it’s just too beautiful to pass up.
I own quite a few maxi skirts from Zara, and they never disappoint.
Don’t stop wearing your favorite flats just because it’s freezing out—just find yourself a nice pair of cashmere socks.
I’ve seen dozens of types of ballet flats recently from square-toed options to delicate satin pairs, but this fiery red pair has to be a top favorite.
The fitted silhouette makes this shirt feel a lot more high-end.
The more versatile an item, the better.
A cape that’s chic enough for a fashion superhero.
Don’t give up warmth in the name of fashion.
I recently test-drove a few Abercrombie pieces, and by far the most worth-it pieces are their trousers, pants, and jeans.
I can’t stop thinking about draped dresses like this, thanks to Hailey Bieber and Saint Laurent.
When Loewe’s spring 2023 collection was filled with Antharium details, the fashion crowd was quick include their own take on florals within their ensembles.
Easy and chic.
Mini in size but big in style.
If you’ve already gotten ed tights, consider your next color choice to be oxblood for a more moodier option.
Would this be a classic 99 under $99 without featuring this J.Crew cuff? It’s a must.
Be the office siren with this shirt. (If your dress code, allows, of course. Fashion offices tend to be a tad more lenient.)
To my surprise, my sequin pants from H&M are something I reach for quite a bit. Whether it’s a dinner, brand event, or holiday party, I won’t mind re-wearing them.
Bonus points: You can customize this bag with your initials!
I promise this is the last striped sweater I’ll include. It was just too good not to.
I currently don’t have the funds to splurge on cashmere or leather gloves right now, so this cozy pair made with a blend will have to do.
I’m telling you—don’t sleep on Uniqlo’s sweater selection. (Their T-shirts are also really great.)
I love the look of a cinched blazer, but I’ll never get over the relaxed feel of a blazer like this one. (Sorry!)
After finding success with the basics I purchases from Gap, I’m not intrigued by their more trendier pieces, like these satin cargo pants.
When winter comes, it’s hard to resist fuzzy accessories like this one.
I don’t tend to look through Zara’s jewelry section, but lately, a lot of pieces have been catching my eye.
Sparkly but not tacky.
When winter arrives, the furry accessories come out.
The patchwork detailing makes this feel so much more fresher than other slip dresses.
Haven’t you gotten the memo? Anthropologie’s handbag selection is impressing the masses. (Who What Wear editors included.)
Just add sheer tights and slingback heels, and you’re ready to impress.
Just think about the cost-per-wear, since you’ll probably be wearing this belt a lot.
There are so many ways this skirt can be styled, but isn’t this way just so incredibly cool?
I recently gave this scarf as a gift for one of my friends who is a fellow cozy girl, and she can’t stop wearing it.
For the risk-takers.
I’ll take all three colors, please.
This color palette is so divine.
This may not be everyone’s taste, but I think this sporty bag is worthy of hype.
