Fall Date Night Outfits | JillianEversole
Fall Date Night Outfits | JillianEversole

Fall Date Night Outfits

Charleston, South Carolina
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Date nights can be such an underrated part of a relationship. They offer a dedicated time for couples to be together, which can somehow become more challenging to accomplish than one would ever expect – I know I can attest to this. Edwin and I see each other constantly but it’s not the same as securing childcare, blocking out our schedules, getting dressed up, and heading out the door for a date night. Date nights are really just a way to keep relationships burning bright and to enjoy the beauty of togetherness! I so often yearn for togetherness without all the distractions of life at home, phones, and emails.

Is it just me or, in the comforting embrace of fall, do you think date nights take on an added layer of magic. The crisp temperatures, the festive tone in the air, and the cozy ambiance of the season lend a special charm to every outing, making these evenings somehow feel more memorable. I’m going against the grain here but, I don’t mind daylight savings on either end of the calendar. In the autumn and winter, I love the extended nights because they feel fitting and feel special. As the seasons change from warm to cool and from fall to the festive season, the sartorial aspect of date nights (or any nights out for that matter) becomes a fun part of the whole experience.

Choosing your perfect fall date night outfits involves considering the activity, the venue, and your personal style to feel confident this season. Many of the items in this post would be brilliant to wear on Thanksgiving too!

Fall Date Night Outfits

I’ve rounded up a curated collection of fall date night outfits that span from casual chic to sophisticated elegance, capturing the spectrum of experiences that this season offers. From layered looks perfect for a leisurely stroll to your favorite wine bar to glamorous ensembles ideal for a night at a chic new restaurant, these wardrobe items aim to inspire your wardrobe this season and next.

Chic ideas for fall date night outfits | JillianEversole.com
Fall Date Night Outfits | JillianEversole

Ulla Johnson Top (long sleeve version) / Ulla Johnson Skirt (more sizes here) / J.Lowery Purse (more colors here) / Margaux Sandals (old – similar, similar)

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Inspired date night outfits for the holiday season | JillianEversole.com
Feather accessories for fall and the holidays | JillianEversole.com

All black outfit for fall and winter | JillianEversole.com
All black outfit for fall and winter | JillianEversole.com

Fall Date Night Outfit Ideas

Black-on-black date night outfit

My puff sleeve black top (similar, similar) paired with a coordinating black midi skirt (more sizes here) strikes the perfect balance of modernity and timeless + casual and chic when it comes to date night outfits. Even though my outfit is all black, the structured silhouette of the top adds a touch of drama and flair to the outfit, while the flowing midi skirt exudes a more dressed up look than if I had just paired the top with a straight leg denim or trouser or pair of black jeans (I’m not a big black jeans gal but I do love these). This ensemble exquisitely balances chic style and comfort, making it an ideal choice for a fall date night. The rich black hue complements the autumnal ambiance, offering a classic yet versatile canvas for accessorizing.

Easily add a little flair to this black-on-black outfit with accessories. For outfit inspiration for this look or similar fall date outfits, consider accentuating the ensemble with statement earrings or a delicate necklace to add a touch of sparkle. Layering with a cropped jacket or a patterned scarf could bring an extra dimension to the look, especially as the temperatures begin to drop in the fall evenings.

How to complete the look

I decided to complete my look with my most comfortable strappy heels (old Margaux heels – similar, similar) and punchy party feather purse. It was a warmer night for the fall season, so I didn’t need a closed toe shoe, tights, or a jacket. But I did want to balance my open toes sandals with the fall glam of my purse, so I went with feathers! If it was chilly, I could have just as easily completed the outfit with sleek tall boots (like these or these) or elegant pumps for a touch of refinement. The beauty of this ensemble lies in its ability to be dressed up or down, allowing for a seamless transition from a sophisticated dinner to a leisurely evening stroll, making it a versatile and effortlessly stylish choice for a memorable fall date night.

I love this top and skirt set because I can also easily wear each item as separates to create different cool weather outfits. The skirt would pair perfectly with a long sleeve tee and a denim jacket for a casual date night outfit (or a daytime fall outing with littles to go apple picking) or you could dress it up worn over heeled knee high boots and an elegant sweater for an evening that calls for a touch of glamour and an outfit that gives you a little extra warmth. Similarly, the top could be worn with chic straight leg jeans, beautiful flats, and a catch-all bag (black or brown) for easy daytime wear or a fall date night to the movies.

I hope this post gives you lots of fall date night outfit ideas.

I compiled some beautiful fall date night wardrobe items below. You’ll find blouses, midi skirts, and heels along with sweater dresses, coats, and boots. Because I love separates but I also can’t resist a dress and boots.

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