If you're unsure what to wear for your big date and need to account for the crisp and colder weather often synonymous with the Fall and Winter seasons, you've come to the right place!
I think that Fall and Winter provide the best opportunities for men to showcase a tremendous amount of variety concerning personal style because these ensembles bring texture, darker hues, and tones, as well as opportunities to layer certain pieces in various ways.
What we wear isn't everything; it won't matter how good you look if you're not endeavoring to be as high-value of a man as possible; however, what we wear says something about who we are and can help us appear put-together and self-respecting. After all, healthy people attract other healthy people, and looking like we are men who show up for ourselves by dressing well is something any high-caliber woman will notice and appreciate.
It's also important to note that if a woman takes time out of her schedule to spend with you, it is simply becoming of any gentleman to try to dress presentably for her.
FALL OUTFITS
LOOK #1: DENIM JACKET & CRIMSON CHINOS
I'm a sucker for a classic denim trucker jacket, and I believe every man should own at least one. It's a timeless and exceedingly versatile piece that can be an exceptional alternative to a leather jacket due to its affordability. Here, I have paired a denim jacket with some crimson chinos and a gray oxford-cloth button-down (OCBD) shirt.
A more classic ensemble would include khaki chinos and a white OCBD, but given the nature of the Fall months, opting for darker hues can be a great way to elevate any look, so long as it's done tastefully. To complete this fit, I added a ballcap to lean into a casual direction and some suede Chelsea boots in a light sand color.
Simple yet decidedly elevated. This look is for the more laid-back dates where you'd want to look put-together without being too dressy (i.e., casual dinner or coffee dates).
LOOK #2: DENIM JACKET & TURTLENECK
Sticking with the same denim jacket as the first look, I added a simple black turtleneck and matching black chinos. Turtlenecks are flattering to men with slender or athletic frames and serve as a subtle way to tastefully elevate the look of a casual and often rugged denim jacket.
This is perfect for the latter autumn months when the temperature has the potential to drop considerably. Adding a scarf to this look wouldn't be a bad idea if warranted, and adding the beanie helps provide additional warmth.
To top it all off, I have incorporated some contrasting suede Chelsea boots in a rich brown that stands out just enough without being too loud. You'll see these exact boots in later outfits on this list.
LOOK #3: CABLE-KNIT SWEATER & BLAZER
Every man needs a quality navy blazer in his closet due to its timeless elegance and classic silhouette. This next outfit is perfect for the holidays, especially for events where you want to get some use out of your navy blazer. I have paired this hopsack variant with a chunky gray cable-knit sweater, deep gray cotton dress pants, brown loafers, and navy socks. Navy blue looks classy when paired with various shades of gray. This look is a terrific example of elevating an otherwise simple and casual look by adding a classic menswear staple such as the quintessential blazer.
LOOK #4: BRICK BOMBER & BLACK
Sticking with bombers, here is a brick red bomber jacket paired with a black turtleneck sweater, the same black trousers as before, and a pair of suede Chelsea boots in ash. Again, this is a casual look that's slightly elevated due to the inclusion of the turtleneck and suede Chelsea's. Every man ought to own at least one turtleneck sweater in either black, gray, or navy blue.
For trimmer and fitter gents, this is an exceedingly flattering piece with which you can do much. Including the suede Chelsea's enhances the look and gives a slight edge while maintaining an air of sophistication. The red bomber is an excellent statement piece but isn't distracting.
LOOK #5: CLASSIC CARDIGAN & CHUKKAS
What can I say? Men shouldn't pass up a timeless navy or charcoal cardigan sweater. Admittedly, this particular look is quite dapper and intelligent (not so much formal), but no one will argue that you don't look like the smartest guy in the room (even if you're not).
Regarding cardigans, it's best to stick with the basics such as charcoal, navy, camel/tan, etc. If you're like me, navy blue works with various styles and can be mixed and matched effortlessly with multiple washes of denim jeans or chinos.
With this specific look, I have completed it by opting for a classic and clean pair of brown chukka boots. This fit is excellent for a slightly more formal date where the necessity to dress more intelligently is present.
LOOK #6: COZY SHACKET & CHUKKAS
A cross between a shirt and a jacket, the "shacket," is a great way to stand out from the rest of the male crowd. In this particular case, this knit shacket has an intriguing texture that pairs well with darker denim. The hints of white thread within it are subtle enough to enable a white crewneck t-shirt underneath, avoiding abrupt contrast. The bottom half of this look is identical to the previous outfit, but the tone is less intelligent and instead cozier. Perfect for coffee and/or brunch dates.
LOOK #7: SUEDE JACKET & CABLE-KNIT SWEATER
One of my all-time favorite types of looks and one that I lean on heavily. A quality suede leather jacket in rich tobacco such as this is a standout piece that all men could benefit greatly from wearing. Adding a cable-knit sweater in a creamy beige is something most women will love. Nothing personifies "cozy elegance" quite like a chunky cable-knit sweater, and pairing these two pieces with a timeless pair of dark wash denim and matching brown suede boots is simply textbook.
LOOK #8: SUEDE JACKET, CHINOS, & SNEAKERS
Okay, so you want to rock that suede jacket but lean more in the casual direction; perhaps where you live isn't so chilly during the Fall. A look like this is excellent for those milder autumn periods. I want to highlight the importance of coordinating colors.
Women often notice the details regarding how men dress, namely, the shoes we wear and the colors we use. The clear star is the suede trucker in a rich tobacco color. I matched the jacket's color with my belt and opted for German Army Trainers (GATs) with a classic gum sole. A pair of white minimalist leather sneakers would have been fine, but the gum sole corresponding to the jacket and belt creates this excellent consistency in the overall look.
Texture and material also matter, especially in person. The jacket itself is suede, and the sneakers have gray suede paneling. This is not as apparent in the photo, but rest assured, women often pick up on this subtlety (especially regarding footwear), and I recommend taking note.
The white pique polo is knitted cotton and pairs well with the GAT sneaker's color and texture. Additionally, the pop of white in the ballcap is subtle and jives well with the rest of the fit. The chinos are navy blue, just like the rest of the ballcap. The suede jacket has hues of orange in it and for those unaware, orange and blue are complementary colors, which means they sit opposite of one another on the color wheel.
I have added a timepiece with a brown leather strap and a navy blue dial with white accented markers to complete this look. Cuff the trousers and keep the ballcap if you want to stay more casual; either way, you're ready to offer a subtle flex.
LOOK #9: LEATHER LAYERED
I recognize that quality leather jackets of any kind are investment pieces. But if you had to invest in one, a classic brown leather jacket like this one will do you wonders, trust me. This look is simple: a chocolate leather jacket, a gray v-neck sweater, and a denim (chambray) button-up shirt.
On the bottom half, I've got the same pair of dark-wash denim and brown suede Chelsea boots that you've seen in some of the previous looks. Wearing a different type of brown boot would do just fine, but I wanted to highlight the versatility of these particular suede Chelsea boots from Thursday Boot Company because they're often my go-to's (as you can see).
- Two layers are often acceptable but sometimes not enough; four layers are often too much, but three layers are perfect.
- The outermost layers ought to be thicker materials than the inner layers.
- If you need to remove the outer layers for any reason, the inner layers should work well on their own.
Stick to these rules, and you'll nail the art of layering every time.
LOOK #10: COCKTAILS
Let's take that same navy blazer from before and dress things up a bit. Not every date calls for more formal outfits, but if an evening dinner at a more formal establishment is in store for you and your date, be sure to take this seriously because most women certainly do!
Cocktail attire is historically very formal (at least by today's standards). A black, dark navy, or charcoal suit is usually more appropriate for cocktail events. Still, nowadays, a blazer can do just fine if paired smartly with additional garments.
Here, I have my navy blazer, a black wool turtleneck, and charcoal flannel trousers with black oxford dress shoes. This look creates a sleek, dark silhouette that uses tone and texture to create visual intrigue.
I think the look 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.
WINTER OUTFITS
LOOK #1: CASUAL, COZY, & COOL
To kick things off with our first Winter outfit, we have a chunky cable-knit turtleneck, which, much like the reasons I gave earlier in this post, is an elegant and cozy option that most women will love to see you in. I have opted for the charcoal topcoat, which is more fitted than a typical overcoat, providing a more tailored look. The black chinos complement the coat well; you might notice these suede Chelsea's from Thursday, which are versatile options that can be mixed and matched in various ways.
LOOK #2: CAMEL & BLACK
If you had to own one topcoat, you can't go wrong with charcoal. However, if you want to stay classic but be a little less generic, then a camel coat is, in my opinion, the way to go. Not much else to say here. This classic ensemble will never go out of style for Winter: a camel topcoat, a black or gray turtleneck, and black chinos or jeans. Add black or camel boots or stick with white sneakers; as you can see, it looks dapper regardless of your preference.
LOOK #3: CLASSIC MONOCHROME
Purely monochromatic outfits are considered safe for most men. Just observe most male celebrities, and you'll quickly see that many of them stick to this palette (and for good reason). Sometimes, the best approach is the simplest one, and while I would encourage all men to at least be well-versed in their colors enough to shake things up now and again, in the Winter months, a look like this can be a success for date nights.
What matters more are the specific choices of garments. Here, I have a gray topcoat, black turtleneck, black trousers, and ash suede Chelsea boots. I have even opted for a gray timepiece and charcoal beanie. These pieces combine well to form a sophisticated, masculine, and comfortable look.
LOOK #4: STREET REBEL
This look is for those DTLA folks who love to play around with classic menswear pieces in bold and unique ways.
I do draw the line regarding baggy fits, as I'm still not a fan (despite that being on trend at the moment). This particular look is excellent for ultra-casual dates with women who prefer a more edgy or eccentric style.
Perhaps that special lady in your life is from a place like Los Angeles and chooses to dress like the "cool art teacher." A look like this (depending on what she's wearing) might be a great way to compliment her style.
The point is, always try to compliment your date. Perhaps your tastes differ, but we're looking to be high-value men, and high-value men aren't trying to date for the hell of it; they're looking to cultivate meaningful relationships that will stand the test of time. Being a team player is commensurate with that effort. So be observant of her tastes because you can be sure she carefully observes yours.
LOOK #5: TOPCOAT & SNEAKERS
Sneakers in the Winter? Yes, you can! Look, no one is saying you MUST wear boots in the Winter, always and forever. As much as I love boots, being stationed in sunny San Diego has taught me that not every December day is a boot day. Don't overthink it; make tasteful decisions!
Here, I'm utilizing that chunky cable-knit turtleneck that we have seen before, a charcoal topcoat, classic blue jeans, sneakers, and a ball cap. Throw on some shades if needed, and you're all set! This is a great way to leverage those foundational pieces that every man ought to own when constructing his initial wardrobe.
LOOK #6: PUFFER JACKET & BOOTS
Puffer jackets (a.k.a. "down" jackets) are simple and effective ways to stay warm without stacking too many layers on top of each other. They're also super lightweight and just comfortable in general. This ensemble is also primarily monochromatic, except for the dark olive suede chukkas on my feet.
Now, black boots or even white sneakers would work well for a look like this, but here is my shameless plug for the power of dark olive suede as a boot color for men; I think it is the single most versatile color for men's boots.
LOOK #7: TOPCOAT & OXBLOOD BOOTS
Here is another textbook example of layering for outfits. Again, thicker layers on the outside and thinner layers are being utilized as we work our way in. The outermost piece is a charcoal topcoat, providing much-needed warmth for the brisk weather. The middle layer is a charcoal v-neck sweater, and the inner-most layer is a blue gingham dress collar polo. Gray and blue look excellent together, but the real star, in my opinion, is the oxblood pair of boots.
Oxblood (a.k.a. Color #8) is an exceptionally versatile color that instantly enhances almost any outfit, incorporating darker hues and tones. Brown or even black boots would do just fine here (especially dark olive suede), but don't pass up oxblood because you think it belongs in your grandfather's closet. This is a timeless footwear color that will gain you compliments from others and, more importantly, from your lovely date.
DRESS WELL & REMEMBER YOUR MANNERS
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 your appearance. People take notice when we show up for ourselves and dress the part, often drawing them closer to us.
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 be looking like a million bucks and, more importantly, a man who is worthy to be by your date's side. Be confident (never arrogant) and have a good time!
Now go and be the good man I know you to be.
