There’s always a big temptation to play it safe when it comes to dressing up for special events. Works-for-anything LBDs are almost too easy to fall back on, while your desire to not outshine the bride, hostess or guest of honor (or completely break the bank) might make you lean toward classic silhouettes and low-key colors you can repurpose throughout the year. If that sounds like your formalwear M.O., then this is the season to let it go. We mean, you only get decked out like this a handful of times throughout the year — don’t you deserve to show up to the party in your dream dress (think: trend-leaning, timeless feeling and always flattering)? The answer should be a resounding YES.
For Your College Roomie’s Wedding
“Make a statement in a unique ‘exit dress.’ All about the back details, this dress will make you feel chic and sexy without revealing too much skin.” – Jessica Mullevey, Rent the Runway
Theia Black Matte Dress ($150 Rental, $995 Retail)
Also try: Selected Teodora Maxi Dress With Strappy Back ($162) + Fame and Partners Farrah Maxi Dress With Lace Up Neck and Open Back ($261)
“Go with a dress you actually like and will wear again. Something easy but with a dramatic neckline or open back like the Fleur Dress is special, not stuffy. You can even wear it to brunch the next day.” – Yael Aflalo, Reformation
Reformation Fleur Dress in Strawberry ($298)
Also try: BLQ Basiq Backless Mock-Neck Dress ($172) + Topshop Metallic V-Neck Strappy Midi Dress ($125)
For Your New Neighb’s Housewarming
“Transition the typical ‘girl next door’ floral pattern into fall with a darker palette for a romantic yet friendly vibe.” – Jessica Mullevey, Rent the Runway
Also try: Topshop Floral Romper ($90) + Babaton Prosper Dress ($175)
“I’d probably choose something a bit more casual for this. The Oriole Skirt is low-key enough for a daytime BBQ or pool party, but still works for having drinks that night. Just wrap it up and you’re good to go.“ – Yael Aflalo, Reformation
Reformation Oriole Skirt in Monaco Stripe ($158)
For Your BFF’s Baby/Bridal Shower
“Ditch your basic sheath for an unabashedly feminine style for a baby or bridal shower. Dresses, skirts and rompers with Victorian details like delicate lace or beading are always right.” – Jessica Mullevey, Rent the Runway
STYLESTALKER Visions Skater Dress ($60 Rental, $239 Retail)
“This is a special day for your bestie, so you want to make sure all the attention is on her while still looking nice. Go with something soft and elegant — nothing too over-the-top or that shows too much skin. The Callado Dress is lovely and not too tight, so you have plenty of room to run around, help with gifts and refill mimosas.” – Yael Aflalo, Reformation
Reformation Callado Dress in Buff ($238)
Also try: Forever21 Dolman Shift Dress ($23) + ASOS Popper Side Clean Column Dress ($81)
For Your School’s Homecoming
“Homecoming is just the warm-up/pre-game for prom, but you should still look really cute. The Miramar Dress is more fun than a regular cocktail dress: there’s a bow on it, there’s a little cutout, plus you can tighten up the straps — that way you can dance without having to keep pulling your top up all night.” – Yael Aflalo, Reformation
Reformation Miramar Dress in Cooper ($168)
Also try: ASOS Salon Holographic Fold Pleat Skater Dress ($153) + C/MEO Collective Living Proof Jumpsuit ($176)
For Your Weekend Work Conference
“Black and white options always make a bold yet professional statement. Mixed media fabrics add interest to a black shift and a great statement outerwear piece will keep you warm and pulled-together later in the season.” – Jessica Mullevey, Rent the Runway
Bailey 44 Mia Dress ($55 Rental, $198 Retail) + Elizabeth and James Boyfriend Coat ($95 Rental, $595 Retail)
Also try: re:named Colorblock Dress ($57) + Cupcakes and Cashmere Stahl Shift Dress ($105)
“Business doesn’t have to mean boring. Go with a classic A-line dress like the Betty Dress with a lace-up heel and chic blazer.” – Yael Aflalo, Reformation
Also try: & Other Stories Blue Morph Print Dress ($90) + C/MEO Collective Power Trip Jumpsuit ($180)
For Your Fancy Dinner Date
“The best bet for a dressy dinner date is a sleek, modern style that makes you feel incredible and highlights your figure. You want to be rocking the dress, you don’t want the dress to be wearing you.” – Jessica Mullevey, Rent the Runway
Jay Godfrey Soori Sheath ($75 Rental, $396 Retail)
Also try: WOW Couture Bandage Mesh Panel Dress ($81) + American Apparel Ponte Off-Shoulder Cross Back Dress ($72)
“You want to look great and show off a little without feeling overexposed. The Corsica Dress has a lace-up neckline to highlight your assets, but a longer midi length for some balance on the bottom. Throw on a sexy pair of heels you can actually walk in and you’re there. “
Reformation Corsica Dress in Sprinkles ($218)
Also try: The Firth Label The Poetry in Motion Jumpsuit ($115) + Missguided Frill Bardot Bodycon Dress ($36)
For Your Thanksgiving Festivities
“There are endless opportunities to sport neutrals like black, grey and camel, but why not embrace the biggest colors of the season in burgundy or teal? They’re flattering on virtually every skin tone and bring a subtly festive feel to your look.” – Jessica Mullevey, Rent the Runway
Also try: Sunday Best Chapman Dress ($110) + H&M Short-Sleeved Dress ($25)
For the Perfect Dressy Yet Functional Bag
“For a black tie or cocktail event, go for a structured clutch with an inside pocket and an optional shoulder strap for ultimate functionality.” – Jessica Mullevey, Rent the Runway
Also try: Zara Clutch With Metal Detail ($60) + Rebecca Minkoff X Revolve Mini Mac ($195)
Where do you go shopping for your fall formalwear? Tell us how you like to style your look for fall occasions in the comments below.
