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13 Casual Fall Date Night Outfits for Men

10 min

Do you need some outfit inspiration for the autumn season? Keep reading to find what you're looking for.

MAKE THE MOST OF THE AUTUMN MONTHS

I think fall is the best season for a date night outfit, with its crisp temperatures and cozy atmosphere. Selecting the perfect fall date night outfit involves considering the activity, venue, and who the special lady in your life is.

The longer nights during autumn and winter make evening dates more special and memorable. Fall is a great time to showcase your style and get creative with outfits, experimenting with different textures, fabrics, and colors to impress that lovely woman in your life.

To see my list of fall essentials, read my separate article here.

THE PERFECT DATE NIGHT OUTFIT FORMULA

The key to creating a perfect date night look is to find a balance between style and comfort. Consider the occasion and choose an outfit that makes you feel confident.

Date night outfits should be stylish and comfortable, especially for a fall evening. You want to be relaxed so you can focus on your date rather than how your outfit feels on your body. Prioritize incorporating different textures and layering for a warm and cozy look. Don't hesitate to be creative and experiment with your wardrobe (within reason, of course).

FALL DATE NIGHT OUTFIT IDEAS FOR MEN

OUTFIT #1: DENIM JACKET & CRIMSON CHINOS

I love classic denim trucker jackets, and I think every man should own at least one. They're timeless and versatile and can be a great alternative to a leather jacket because they're often more affordable.

Read this post here for my complete guide to denim jackets.

For this outfit, I've paired a denim jacket with crimson chinos and a gray oxford-cloth button-down (OCBD) shirt. A more traditional look would include khaki chinos and a white OCBD, but for the fall months, opting for darker colors can be a great way to elevate any look (as long as it's done tastefully).

To complete this outfit, I added a ballcap for an even more casual touch and some suede Chelsea boots in a light sand color. Simple yet elevated, this look is perfect for laid-back dates where you want to look put-together without being too dressy (such as casual dinners or coffee dates).

OUTFIT #2: SUEDE JACKET & CABLE-KNIT SWEATER

Here is one of my all-time favorite looks featuring a quality suede leather jacket in a rich tobacco color. It's a standout piece that all men could benefit from wearing. Pairing it with a cable-knit sweater in a creamy beige is a great choice that most women will love.

A chunky cable-knit sweater epitomizes "cozy elegance," and when paired with a timeless pair of dark wash denim and matching brown suede boots, it creates a classic and timeless aesthetic. Suede jackets can add texture, sophistication, and ruggedness to any outfit, especially when paired with denim or knit wool for autumn festivities.

A look like this is excellent for milder autumn periods. I also want to highlight the importance of coordinating colors.

For more information about the basics of color, read my separate article here.

Women often pay attention to the finer details of men's clothing, particularly the shoes and colors they choose. The standout piece for this look is the suede trucker jacket in a rich tobacco color. I coordinated the jacket's brown tone with my suede Chelsea boots in the same color.

Texture and material are both important in this outfit. The jacket and Chelsea boots are made of suede leather, while the chunky cable-knit sweater complements the texture of the darker denim trousers.

The rich brown color of the jacket and boots has noticeable tones of orange, which complement the darker shades of blue. For those who may not know, orange and blue are complementary colors, as they are opposite each other on the color wheel.

Complimentary Colors

OUTFIT #3: DENIM JACKET & TURTLENECK

I kept the same denim jacket from the first look and paired it with a simple black turtleneck and matching black chinos. Turtlenecks are flattering for men with slender or athletic frames and offer a subtle way to enhance the appearance of a casual denim jacket.

This ensemble is ideal for late autumn, when the temperature could drop significantly. If needed, adding a scarf to this look would be a good idea, and wearing a beanie provides extra warmth.

To complete the outfit, I included some contrasting suede Chelsea boots in a rich brown shade (similar to the previous outfit). These particular boots stand out just enough without contrasting too much.

Read here for eleven ways to style a classic blue denim jacket.

OUTFIT #4: WINE TASTER

If you're planning to have cocktails with your evening dinner, make sure to dress appropriately. Here's a classic navy blazer paired with additional cozy attire.

Read this article to learn the differences between a blazer and sport coat.

Cocktail attire used to be very formal, but nowadays, a blazer paired with the right clothes can work well. For example, here I have a navy blazer, a black wool turtleneck, charcoal flannel trousers, and black oxford dress shoes. This outfit creates a sleek, dark silhouette with exciting tones and textures.

I think the outfit speaks for itself. Show up wearing this, and your date will be glad she is by your side (provided the place for your date warrants such an ensemble).

OUTFIT #5: SMART CASUAL NAVY BLAZER

Here is another look featuring a classic navy blazer, this time with a gingham-patterned dress collar polo, a heather gray quarter-zip sweater, and classic dark denim jeans.

Read my article here for various ways to style a classic navy blazer.

The clear statement piece here is the pair of oxblood service boots. Oxblood is a color of footwear that I don't see many men rocking these days, but I'd say it's time for a resurgence. You'll find that oxblood can replace conventional brown-colored footwear (depending on the style of shoe/boot) and also elevate your look altogether.

Don't overlook oxblood boots! This look is an excellent example of subtly adding red hues in tasteful and unexpected ways. It's a great look for anyone with a more conservative style.

OUTFIT #6: CASUAL FLANNEL SPORT COAT

A well-fitting, neutral-colored sport coat is always a good choice. For this ensemble, I've chosen a camel sport coat in flannel paired with a black crewneck shirt and dark denim jeans.

Complete the look with olive suede lace-up boots, which complement dark jeans and a flannel jacket. Paying attention to textures can add extra flair to your look, especially when using neutral colors.

OUTFIT #7: CASUAL FLANNEL OVERSHIRT & JEANS

Flannel is often associated with the fall season. This outfit includes a classic flannel overshirt in brilliant crimson red, a plaid flannel button-down shirt underneath, classic dark indigo jeans, and brown chukka boots.

It's a casual yet sophisticated way to use deeper shades and tones of colors to your advantage. Simple, timeless, and elegant. A look like this will look good for decades to come!

For the best fall jackets for men, check out my separate post here.

OUTFIT #8: BURGUNDY SHAWL CARDIGAN & WHITE

Darker red and white look exceptional together. Here, I wear a maroon-red donegal shawl cardigan sweater. Underneath, I'm wearing a navy blue dress collar polo that matches the darker tone of the cardigan.

The white denim provides a clean look alongside the darker sweater and polo shirt. The chocolate loafers and matching navy socks tie everything together, creating an exceptionally dapper and harmonious ensemble.

OUTFIT #9: NEUTRAL COLORED RAINMAN

We need to consider options for rainy weather; this outfit is a great example of using neutral colors effectively. A tan raincoat always pairs well with other classic neutral-colored pieces, like the brown quarter-zip sweater, blue dress-collar polo, and dark denim jeans I've included here.

Read my separate post here to learn why neutral colors are best for men's clothing.

Complete the look with a rugged yet classic pair of boots, such as these Thursday Captain Boots in tobacco brown, and you'll be ready to face the elements with your special someone.

If you'd like to hear what I have to say about Thursday Boot Company, check out my brand review here.

Feel free to wear a classic trench coat if you want to make a bold statement with your style. The trench coat and the previously mentioned macintosh (mac) jacket can be styled similarly, and both will protect you from wet autumn rain.

Banana Republic Factory Trench Coat

OUTFIT #10: FIELD JACKET WITH CHUKKAS

The field jacket is, as it sounds, meant for the great outdoors. Like many historical garments for men, this jacket's roots come from the military. Field jackets can be made of various materials and come in many colors. For a more classic look, go for olive or sage green.

This piece is a utility garment through and through, with several zip or buttoned pockets. Wearing a field jacket can be a great way to remain edgy, rugged, and stylish while allowing ample space to hold your items.

Wear dark wash jeans, chukka boots, and a casual knit shirt, such as a creamy waffle henley, to showcase neutral colors and keep it simple and stylish for your lady.

OUTFIT #11: LEATHER JACKET, WHITE PANTS & BOOTS

A leather jacket is a timeless piece that combines masculinity and sophistication. It's a must-have for any man looking to make a statement this season. When shopping for one, look for a leather jacket with a fitted silhouette and a classic design. Leather jackets are versatile and perfect for both formal and casual occasions.

Whether you choose suede or a traditional leather finish, sticking to neutral colors will work well for any occasion. When paired with a classic leather jacket, white pants, especially denim, can add elegance and boldness to your fall outfits.

Read my separate article here for more inspiration on year-round white pants outfits.

OUTFIT #12: ANALOGOUS HARRINGTON & CHUKKAS

Inspired by Steve McQueen himself, I'm wearing a gingham blue dress collar polo shirt as the base layer, a navy blue v-neck sweater as the mid-layer, and a classic navy Harrington as the outermost layer. This is an example of an analogous color scheme comprised of blue and green.

This can be an excellent option for keeping you warm and cozy in the late fall and early winter. Add your favorite neutral-colored boots, and you're in business!

Analogous colors sit next to each other on the color wheel. This outfit features blue and green, my preferred analogous color combinations. Regarding my choice of dark olive suede boots, I think they can replace brown and black boots in any man's wardrobe.

Analogous Colors
To learn why dark olive suede is the best boot color for men, read this article here.

Harrington jackets have a rich history in menswear and will always look great. Depending on the fabric, Harrington jackets can help shield you from brisk winds and pesky rainfall. Remember that they are lighter jackets that won't offer too much warmth if needed.

Check out my separate article for more green pants outfits here.

If you live somewhere with brisk and frigid fall weather, the next outfit might be more your style.

OUTFIT #13: CLASSIC NAVY PEACOAT

The peacoat is a sophisticated, double-breasted outerwear garment with six buttons and an ulster collar. It is suitable for pairing with a sweater and jeans or a dress shirt, tie, trousers, etc.

If you want something that provides the warmth and structure of an overcoat but isn't as long, then the peacoat will work wonders for you. It's a timeless piece that can be dressed up and down in various ways and even provide some shielding from the elements (though the macintosh, as mentioned earlier, and trench coats will do much better).

For this look, I'm wearing a chic, nautical-inspired outfit. I have a classic navy peacoat, a lighter denim button-down shirt, white jeans, and rich brown chukka boots. White and various shades of blue look stunning together. If you want to be both cozy and elegant, then this is a good option for you!

REMEMBER TO BE A GENTLEMAN

Creating a memorable date night outfit is all about balance. Consider the occasion and what you feel like wearing to boost confidence. Date night outfits should be stylish yet comfortable for a fall evening.

Focus on texture and layering to create a stylish and cozy look. Using layers and darker tones of neutral colors can be a powerful way to communicate to the woman you're with that you're serious about her (and your appearance).

Now smile, open all doors for your date (even car doors), walk on the street side of her, and pay the bill in full. You're lucky to spend time with this woman and ought to treat her like gold.

The good news is that you'll look like a million bucks and, more importantly, a man worthy of being by your date's side. Be confident (never arrogant), and have a good time! Now go and be the good man God fashioned you to be.

"So flee youthful passions and pursue righteousness, faith, love, and peace, along with those who call on the Lord from a pure heart." 2 Timothy 2:22

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