If you’re reading this, we can only assume at least one of two things is true about you. One, you love a good pun. Or two, you have a date coming up, and you are panicking about what to wear. Either way, or both, we have you covered as usual. The fall season brings you a slew of new style options when going on that important date. You get to pick out your best sweaters. You can break out that favorite leather jacket. You can get reacquainted with that trusty pair of boots. Of course, every date idea brings with it etiquette to making the first impression you are going for. Here are some great examples of men’s fall date outfits.
Pumpkin patch outing
Whether you know it or not, every successful relationship is made up of two people. The first is the person who lives for the apple cider donuts, the hayrides, and the entire vibe a pumpkin patch brings. The other is the person who goes just to make their partner happy. We will not be taking questions. No matter which person you are, here is what you should pick up if you want to look great and fall in line with the pumpkin patch vibe.
- Fleece-lined jeans. Sometimes the pumpkin patch is still holding on to the last rays of summer, but for most of us, it is the first foray into the colder weather. Get yourself a nice pair of fleece-lined jeans, and you won’t be miserable while making your partner happy or trying to keep them happy. Pro tip: If the fleece is an interesting color, cuff them to give your outfit depth.
- Waffle-knit henley. This is the unsung hero of your wardrobe, and is one of the best parts of the cooler weather. Break this out for the date and look cool, calm, and collected. If you want to look like you have some forethought, mustard yellow, burgundy, or burnt orange are great colors to make you fit right into the fall weather.
- A field jacket. Like we said, the weather can be unpredictable, so come prepared with a great field jacket. This can be canvas, leather, suede, or even waterproof gaberdine, as long as it keeps you warm and gives you something to offer them when they are cold in the unexpected temperature drop.
- Boots. Look, we said the henley was the best part about the fall, and it might be simply because you can technically wear these all year. But the fall is when the rugged cap-toe boot really shines. If you have a trusty pair that are a few years old, they will look the best. If not, then hopefully you have time to buy a pair and break them in, because nothing looks better than a good pair of worn-in boots.
Stroll through Stars Hollow
We know that Stars Hollow is a fictional place. But doesn’t every small town with changing leaves make you feel like you are in Stars Hollow? No? Just us? Well, that doesn’t mean you won’t be strolling alongside someone who is feeling like they are whisked there, where the romance is alive. So be prepared. Here is what to wear for your leisurely walk.
- Chinos. A good pair of chinos are one of the more versatile items in your closet and these are the ones you will want for your little jaunt across town. Simple, comfortable, functional, like any good pair of pants should be. Stick to your tan colors so they can go with anything,
- Flannel. Should we say it? We aren’t sure we can keep from saying it. We all think we are Luke at the diner in Stars Hollow, so we all know we should have a trusty flannel to go to. Walking around town is a casual thing. You are open to whatever comes along, meaning you need something that goes with you well, and flannel is one of man’s greatest companions.
- A leather jacket. It should probably be brown, just so it can fit in with the vibe of fall. But a leather jacket is the epitome of cool Americana. If you want to exude confidence and calmness, the leather jacket is the tool you should bring. And, like we said, offer it up if your date didn’t bring a jacket.
- Chukka boots. The chukka is a great boot for walking. It is stylish enough to look good on the date but comfortable enough that your dogs won’t bark by the time you are finished. If you want to step this whole outfit up, opt for suede leather for both the jacket and the boots.
Scary movie night
It is spooky season. Fall is about Halloween, with Thanksgiving thrown on top of it. Can we have a moment of recognition for the middle child of the holidays? Anyway, fall has an entire month of scary movies, so it is entirely possible that a scary movie date is on the docket. But what do you wear to look like a date but be comfortable for couch watching? Simple…
- Performance denim. The last thing you want to do for a date is wear sweats or pajamas, even for a movie date. While there are some joggers out there you can get away with, it may be best to opt for performance denim so you get the elevation of denim along with the comfort of athletic pants.
- A luxury tee. Let’s be honest: You are going to be lounging and watching movies, so comfort is key to the look. Stay comfortable but look like casual perfection in an elevated crisp tee. Make this a solid. There is no need for graphics on this one.
- A cardigan. Here it is, the way you take the outfit from casual lounging on the couch to date night. The cardigan is an underutilized treasure in your wardrobe and this is the perfect moment for it. It is cozy, attractive, and is perfect to cuddle with. Feel free to thank us.
- Clean sneakers. We say clean in the traditional sense, not the slang sense. Sneakers are a great choice for this look because you can slip them off easily when you walk through the door. Please slip them off when you go in, or the date will start on red flags. But just because they are left at the door doesn’t mean they won’t be staring at them and finding out what kind of man you are by the care of your shoes during boring parts of the movie, so might as well make them clean.
Dinner and drinks
If it is a first date, this will likely be the place to start. A night on the town in the fall is a great way to get to know someone in a comfortable and serene environment. The fall also offers some great items you can wear to render your date unable to peel their gaze from you. Here are some items to throw together to give you an edge:
- Wool pants. Vintage is in, so this look is going to reach back and pull from our ancestors (not that far back, don’t worry). Getting a pair of thicker, worsted wool pants will give you an elevated casual that will be hard not to notice. It shows a deep understanding of men’s styles and trends.
- A tweed jacket. Speaking of style and trends, the tweed jacket is back. No longer is it meant to stay in the closets of our grandfathers and professors. Instead, it is leaping back into the forefront of style. If you can find one with a leather patch on the shoulder, reminiscent of the English fox hunt jacket, all the better.
- A dress shirt. Wearing a basic dress shirt open at the collar shows you are relaxed and comfortable. It allows them to feel the same. If you look tight, they will tighten. Leave the top button undone on an ecru-colored shirt (buy into the old-fashioned vibe here) and engage in smooth conversation.
- Oxfords. Not sure if you picked up the vibe, but this look is going for an English autumn. Oxfords are classic dress shoes and will look amazing with virtually anything you pair them with. But in this situation, they complete the vibe we’re going for.
Drive to see the leaves
Traditions exist for a reason. They happen because the activities you make traditions are ones that everyone loves. Driving down a country road to see the leaves change is one of the oldest traditions for the fall. If you are the kind of person that has done this each year, you may begin to take it for granted. Lock in, it may be the last time you do it with someone for the first time. Relish it.
- Dress denim. The look for this date will be casual—it is essentially a mini road trip. But there are ways to elevate your look so you don’t seem too nonchalant. Dress denim is dark with a slim silhouette, so you can also use performance denim for added comfort.
- A long-sleeve cashmere polo. This may sound specific, and it is a little. The polo is a great smart, versatile, casual look if you stop off for food. The cashmere is soft and comfortable for you, and impossible to resist leaning on for them. If you want to elevate the look, make the whole look monochromatic.
- Chelsea boots. Casual but elevated—there may be a theme evolving here. This is the best shoe in the world for the guy who needs something casual but versatile. This is the perfect time to utilize the versatility by wearing them to drive around in a serene environment.
- A cravat. We know what you are thinking. “A what?” Trust us, these are starting to blow up in the U.S. thanks to the undying dedication to the style across the water. It is a simple way to elevate any outfit from basic and boring to deep and thoughtful. If you are going monochromatic, make this stand out slightly. For example, if you are going all black with your choices (not a bad plan at all), the cravat should be black with white dots. Something subtle.
There you have it, ideas for the outfits that will get you from date one to date two. And, if you hadn’t already planned them, it may have even given you some ideas for dates. But, don’t offer to take them to Stars Hollow until you look it up.
