Published on Nov 20, 2025 at 1:05 PM
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The holidays are so often about giving to those around you that it can be easy to put your own needs on the back burner. That is, until you remember you have a party to attend next week and then your most pressing need becomes finding something to wear. No matter what celebratory get-together you've got on the calendar, a one-and-done dress is the easiest way to nail the dress code (both explicit and implicit) every single time.
From a flirty cocktail mini to a sophisticated black-tie gown, here's a selection of dresses under $300 that will take you through the party circuit. It may be the season of giving, but you can consider treating yourself to a cute new dress a generous act of self care.
Macy'sFor a Cozy Get-Together
Lioness Long-Sleeve Field of Dreams Maxi Dress ($109)
This maxi number may look like it's taking "cozy" three steps too far, but don't be deceived by the elegant off-the-shoulder silhouette and romantic burgundy hue. It's surprisingly comfy thanks to the fluid jersey material that's soft and forgiving — exactly what you want to be wearing for a more relaxed social gathering that no doubt will include a lot of sitting around.
Macy'sFor a Cocktail Party
Avec Les Filles Long-Sleeve Stretch Velvet Mini Dress ($148)
This season, swap your little black dress for a little green velvet dress instead. With the playful chartreuse color and sparkly buttons at the neckline and sleeves, it's flirty and striking, but in a subtle and demure way.
Macy'sFor a Work Party
Karen Millen Asymmetric Strap Knit Midi Dress ($241)
For a more conservative setting, you can't go wrong with a sheath-style dress — just amp up the details. The details in question? Asymmetric, architectural straps that lend a contemporary flair to an otherwise simple and sophisticated shape.
ASOSFor a Family Reunion
ASOS DESIGN Crew Neck Short Sleeve Velvet Midi Dress ($95)
If you need a dress that doesn't necessarily call attention to yourself but still makes you look and feel fantastic, opt for this cap-sleeve midi dress. The luxe velvet texture and sophisticated cinched waist silhouette create an overall effect that looks way more elevated than the $95 price tag. Add a few high-end accessories and the only thing Grandma is commenting at this year's family party is how nice you look.
Banana RepublicFor a Winter Wonderland Party
Banana Republic Stretch-Satin Cape Maxi Dress ($280)
If you've been invited to a "winter wonderland" extravaganza, the challenge is finding a dress that feels glamorous without leaning too much into bridal territory. This low-cut column dress with an attached cape strikes the right note: it's refined and angelic, while still feeling fresh. Throw on some opera gloves and you'll be a vision in understated elegance.
Amanda UprichardFor a Holiday Wedding
Amanda Uprichard Jada Dress ($299)
A winter wedding is your opportunity to play around with rich style elements that you wouldn't typically get to indulge in for a spring or summer wedding. Think: holiday or jewel tones, luxe textures like velvet or faux fur, sequins, even sleeves. This Poinsettia-red dress is fun and unexpected with the lace underlay, and won't restrict you from hitting the dance floor. Add some metallic accessories and a cropped faux fur coat coat to amp up the glam.
Macy'sFor Friendsgiving
ASTR the Label Crewneck Dress ($164)
Your friends will forgive you for showing up to Friendsgiving wearing sweats, but why should you when this slip dress is (almost) just as comfortable and 10 times more stylish? You don't need an elastic waistband when you've got a bias cut that skims your figure without clinging and billowy sleeves that aren't restricting. It's a dress that allows you to sit and eat comfortably, second servings withstanding.
Simon MillerFor a Gift Exchange
Simon Miller Fountain Metallic Mini Dress ($295)
A white elephant party, Secret Santa, or gift exchange with your closest friends is the ideal scenario to show up in your boldest and brightest. After all, no one will appreciate your outfit in the way your besties can. This metallic shift mini is so fun and merry, it's almost as if you're the gift under the tree.
MeshkiFor a Black Tie Gala
Meshki Michelle Cut-Out Maxi Dress ($265)
A black-tie event is arguably one of the toughest occasions to shop for — you want a floor-length gown that's formal (no thigh-high slits!) and crafted from an evening-appropriate fabric (no cotton or linen!). While there are no rules against wearing specific colors, black is a classic choice you can't go wrong with. This column gown is sleek and sharp, with structured shoulders and a high neck, but still sultry with the cut-out. Complete your look with a slicked-back hairdo.
Macy'sFor a New Year's Eve Bash
RACHEL Rachel Roy Strapless Sequin Midi Dress ($159)
Sequins for New Year's Eve certainly isn't a groundbreaking combo, but you can't deny it's fun to lean into. The dazzling, liquid-like shimmer of this silver stunner is balanced with the minimalist cut for a look that's clean and modern. Throw it on with black accessories and an oversized blazer for a sophisticated take or under a fuzzy cropped sweater and tall boots if you want to tone down the shine.

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