7 Fall Date Night Outfits that Exude Autumnal Romance

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At least once a week, I make it a priority to carve out some time for a proper date with my boyfriend. Whether we're planning an intimate dinner at a restaurant, sipping coffees at our go-to café, or getting a bit more adventurous with activities like painting or museum hopping, we make an effort to spend quality time together. But as date night approaches, there's always the challenging task of finding the perfect date night outfit to set the mood just right.

If you’re like me and are in search of fall date outfits to add some romance to your autumn wardrobe, I've got you covered with these 7 fall date night outfit ideas. No matter the occasion, whether it’s visiting a pumpkin patch or sharing cocktails on a rooftop bar, there’s a stylish look to help you look and feel your best on your next date. Continue reading to discover 7 romantic date night outfits for the fall season.

How to Dress for Fall Date Night

1. Layer, Layer, Layer

Fall weather can be unpredictable, so layering is key. Always start with a stylish base outfit and add layers like cardigans, blazers, or lightweight jackets that you can easily remove if you get too warm. You might also bring a scarf, hat and gloves if the weather is particularly cool.

2. Opt for Seasonal Colors

When dressing for a date, choose fall-appropriate hues like deep reds, burgundy, mustard yellow, olive green, and rich browns. Find colors that simultaneously work with your personal color season. For example, as a warm spring, I like to wear camel, cream, golden yellows and red-orange during the fall months.

3. Pick Textured Fabrics

Incorporate textured fabrics like tweed, corduroy, suede, or knitwear. These will not only keep you warm but also add depth to your fall date night outfit.

4. Invest in Boots

Boots are a must for fall date nights. Whether ankle boots, knee-high boots, or over-the-knee boots, they are a comfortable footwear option that goes with almost everything. Wear them with knit dresses or a blouse and jeans, they’re a must-have essential for your fall wardrobe.

5. Keep Tights or Leggings on Hand

If your date night outfit involves a dress or skirt, consider wearing opaque tights or leggings to stay warm while looking stylish. Stock up on a few pairs to keep in your closet for those cool autumn nights.

Fall Date Night Outfit Inspiration

Fall Date Night Outfits

1. Long-Sleeve Top + Pencil Skirt + Heeled Boots

For those fall date nights when you want to exude elegance and confidence, consider this chic combination of a long-sleeve top and a pencil skirt. A longs-sleeve top or sweater not only keeps you cozy as the temperatures drop but also adds an air of sophistication to your look. Opt for rich fall colors like deep burgundy, forest green, or keep it classic with white or black. Create a flattering silhouette by adding a long pencil skirt. Choose a skirt in a textured fabric like tweed or a rich wool blend to embrace the season's textures.

To elongate your legs and add a touch of allure, slip into a pair of heeled ankle boots. Add a polished touch to the ensemble with a slender belt. A top handle bag pairs beautifully with this outfit, and it's perfect for carrying your essentials while you're out and about. Whether you're heading to a romantic dinner, an art gallery opening, or a sophisticated happy hour, this easy combo is versatile enough to suit a range of fall date night settings.

2. Sweater + Skort + Kitten Heels

If you're on the hunt for a fall date night outfit that seamlessly transition into your autumn wardrobe, look no further than this sweater and skort combo. Perfect for a casual dinner date or an afternoon at a museum, this versatile ensemble is will help you create a romantic look that radiates effortless charm.

Begin with a cozy sweater in a warm, autumn-inspired hue or pattern. It’ll ensure you feel comfortable on cool fall evenings without sacrificing style. Choose a skort or a pair of structured shorts in a classic neutral hue or try an autumnal pattern like plaid or houndstooth. Layer a pair of sheer tights underneath your skort for an additional layer of warmth (and sophistication).

A pair of kitten heels is ideal for a romantic fall date night. These low-heeled shoes are a must-have in my evening wardrobe because of their practicality. They add some elegance to your look, but they are much more comfortable than a pair of pumps or stilettos. Try a trending color like bordeaux for an chic pop of color. Complete your date night look with a matching shoulder bag to carry all your essentials in style.

3. Long-Sleeve Top + Mini Skirt + Heeled Boots

Balance comfort and elegance with this romantic fall date night ensemble. A basic long-sleeve top provides warmth and adds a casual touch to your look. Add some flirtatious charm with a mini skirt — I’m loving the micro skirt trend that I’m seeing everywhere this season. Try a classic black option or experiment with fun pinstripe or suede styles.

Complete your look with a pair of heeled boots and a structured shoulder bag to effortlessly elevate your outfit. If you need extra layers, you can easily throw a basic blazer over this ensemble. So whether you're enjoying a romantic dinner or embarking on a night out on the town, this easy combo is the perfect outfit for any fall date. Definitely add this look to your date night outfits Pinterest board!

Related Post: The Fall 2023 Trend Report

4. Bomber Jacket + Jeans + Ankle Boots

For a casual date night look, I’m always reaching for a pair of jeans and a cool jacket. It’s an effortless combination that is perfect for attending a fall festival, taking a scenic evening walk, or even spending an afternoon at a pumpkin patch. This casual ensemble features a trendy brown bomber jacket that is perfect for those crisp fall nights. Its versatility makes it an excellent choice to pair with various outfits throughout the season.

Underneath your bomber jacket, layer a cozy sweater like a classic black turtleneck. Pair it with straight-leg or bootcut jeans in a classic wash. To upgrade your date night outfit, wear a pair of ankle boots that coordinate with your jacket and add a brown shoulder bag for the final touch. This look makes dressing for a date so easy.

5. Knit Dress + Belt + Heeled Boots

When I’m stumped on what to wear, my trusty timeless knit dress in the closet always comes in clutch. Dress it down with flats and a hobo bag for a casual day out or transform it into a sophisticated date night outfit with heeled boots and a belt.

For this particular fall date night ensemble, I've opted for a long dress that embodies both sophistication and modesty. When selecting a knit dress, consider a length that makes you feel comfortably confident, such as a midi or knee-length option. To accentuate your figure, don't forget to cinch it with a belt. You can try a statement belt for a bolder look or go for a more classic slender style.

Heeled boots are the perfect footwear for fall date nights. Depending on your dress length and personal style, choose between ankle or knee-high heeled boots. Personally, I love the elegant look of tall boots beneath a long knit dress. Elevate your look with accessories like statement earrings and a chic shoulder bag. And, if the weather requires it, consider adding sheer tights or knee-high socks to ensure extra warmth without compromising style.

6. Silky Blouse + Jeans + Kitten Heels

Dressing for a date can be effortless when you stick with the timeless “nice top and jeans” formula. A cream silk blouse is one wardrobe essential that you can easily dress up for your next autumn date night. Pair your cream silk blouse with well-fitted jeans that flatter your body shape. Opt for a clean, dark wash for a sleek and polished appearance. The contrast between the silk blouse and denim adds a touch of casual sophistication to your look.

Elevate your outfit with a pair of kitten heels for sophistication and comfort. Add a matching shoulder bag to complete your date night look.

For the working girl, this outfit is ideal for those post-office dates. Consider swapping the jeans for trousers for a seamless transition from office to evening. Alternatively, you can pack a pair of jeans in your work tote to change into before your date, so you're ready for whatever the evening brings.

7. Monochromatic Ensemble + Long Coat + Colorful Boots

Monochromatic dressing, while effortlessly chic, may occasionally feel a bit predictable. However, there's an easy way to make your monochromatic ensemble more suitable for fall - introduce pops of color in autumn hues.

Begin by selecting a monochromatic base for your outfit. For this fall date night ensemble, I've opted for a classic black crewneck sweater paired with a matching mini skirt. To infuse a sense of warmth and refinement into your overall look, consider a long coat in a mossy green hue, or whichever color suits you best.

Infuse more color into your ensemble by opting for a pair of colorful boots. Consider jewel-toned boots like emerald green, royal blue, or deep red to create a striking contrast against your monochromatic base. Red is the color of the season, so for this outfit I’ve opted for a ruby red pair for a trendy choice. Now you’re ready for a fall night out!

What do you wear for fall date night? Let me know in the comments below.