What Not To Wear On A Date This Fall: 10 Fashion Trends Men Hate

Fall is undoubtedly the most highly anticipated time of year for many of us. We gleefully switch out our typical vanilla lattes for something with a pumpkin spice zing to it, excitedly stock up on every cozy candle we come across at Target, and last but definitely not least, we exuberantly pull out our sweaters and long-sleeved shirts once again, to help us concoct the perfect fall outfits all season long.

But we don’t just stick with the old tried-and-trues of our autumn wardrobe every year, like our ankle boots, chunky sweaters, and leather jackets. We also add new pieces to it. We pay attention to whatever new fashion trend is taking over that fall and eagerly take part in it. We see one or two influencers wearing a piece we don’t yet own and think, I have to have it.

And yet, the guys don’t necessarily agree with us about every fall fashion trend. Do you really have to have that pair of shoes? they think. While we might have assumed that the average man isn’t all that into fashion, and therefore, doesn’t have any opinions on what we wear, this simply isn’t the case. In fact, there are a number of autumnal fashion trends that are popular with the ladies that guys not only don’t understand the appeal of, but would see a girl wear on a first date and find it downright unattractive – yikes.

What are these trends that would apparently make such a bad first impression? And what should you try wearing instead? We asked the guys for their unfiltered thoughts, and here’s what they had to say.

Clunky Shoes with Socks

We get it – clunky slip-ons are comfortable and seem like they'd be the perfect choice for a casual coffee date. They’re so easy to get on and off, and offer something a little bit different from the sandals you’ve been wearing all summer long. And to make them a little more autumnal and keep your feet warmer, you think, you’ll wear them with socks. But all the guys see is “feet that look like hooves with socks coming out of them." We’ll admit, these aren’t the most feminine shoes in the world.

What to wear instead: A pair of sock boots will still give you that tapered “sock” look, but kick it up a few notches, taking the silhouette from decidedly frumpy to undeniably sleek and cool. Plus, they’ll pair perfectly with most pieces in your closet.

Bucket Hats

We might think bucket hats are adorable, nostalgic, and fun…but the guys are not in agreement. Rather than making a girl look cute, guys think they’re “shlubby, ugly, and obscure any beauty she has.” To them, bucket hats are distracting and make too much of a statement: “It’s kind of like, alright, we get it, you’re quirky.”

What to wear instead: Depending on the outfit and the date activity, we’d recommend wearing a beanie if your main concern is to keep your head warm without sacrificing your ensemble’s chicness – the guys didn’t seem to have anything negative to say about this classic cap.

Super Baggy Jeans

It’s no secret that super baggy jeans have been the denim of choice for the last couple of years with Gen Z, edging out every millennial’s favorite skinny jean. But many men aren’t on board: “They just look messy and sloppy. They totally hide her form. There’s a reason we look at the baggy suits men used to wear and cringe – they don’t look sharp.” Another comment that stood out? “It looks try-hard.”

What to wear instead: If you aren’t a fan of skinny jeans, you certainly can’t go wrong with some fitted mom jeans or not-too-loose boyfriend jeans. So you don’t get lost in a sea of fabric, pair them with a more fitted top for some juxtaposition and balance in your look.

Ugg Boots

Our inner mid-2000s selves are weeping. Of the pieces that were mentioned by the guys we asked, Ugg boots were by far the most mentioned, and the most disliked. “They look comfortable, but kind of childish. It’s a little like wearing pajama pants out in public.” Perhaps it’s best to keep your cozy Ugg boots as inside-only footwear?

What to wear instead: We get it if you don’t want to wear heels, but one way around this that the majority of guys like? Combat boots. Pair them with something on the more feminine side to strike a nice “cool girl” balance between hard and soft.

Oversized Leather Jackets

We’re cozy in our way-oversized leather jackets. They feel like wearing a hug, but one that makes us look cool. But it might be best to not reach for it for a first date, because according to the guys, they’re not the vibe: “I like leather jackets, but these look haphazard. They’re too boxy and masculine.”

What to wear instead: That being said, men are fans of leather jackets in general – just when they’re a little more fitted. Try wearing that moto jacket or that leather blazer instead, and there’s no doubt he’ll be interested.

Birkenstock Sandals

Are Birkenstocks some of the most comfortable footwear we’ll ever come across? Without a doubt. Does that mean they’re automatically cute enough to wear on a first date? Unfortunately not. Many men have long complained about Birkenstocks (especially the fuzzy ones), calling them “unbecoming, dowdy, and not feminine.” Sad to hear, but perhaps they have a point.

What to wear instead: If you want to stay away from high heels, we’d suggest going for a pair of kitten heels. They’re feminine and can be paired with just about anything, from jeans to a maxi dress.

Wide-Brimmed Hats

You know the hat we’re talking about – the hat that sits on your closet shelf for months on end, until that mid-September or early-October day, when the air has a chill to it. To us, they’re the epitome of autumn. We imagine carving pumpkins, sipping the first PSL of the season, and playing in the fall leaves in this hat, wearing it all season long. But the guys wish we’d just leave them at home more often: “These aren’t the worst, but I’m not a fan of seeing basically every girl wear them everywhere. They all end up looking like clones. Again, I don’t hate them. I just don’t want to see them all the time.”

What to wear instead: Instead of never wearing your wide-brimmed hat again, try wearing it only for activities when it would make sense, like a music festival, your apple picking adventures, or a leisurely hike. 

Denim Maxi Skirts

Sure, it’s a different look. It’s probably something most of us haven’t tried before, and after seeing a denim maxi skirt pop up enough times on our FYP, we might be tempted to try wearing one…but guys are not neutral on them: “They’re just so frumpy. I can’t imagine even a gorgeous woman looking good in a denim maxi skirt.”

What to wear instead: Don’t give up on maxi skirts altogether. Just pick one that is more on the feminine side – soft and flowy. Consider pairing it with some boots for a decidedly autumnal look.

Newsie Caps

Ah, newsie hats. We think they’re cute, stylish, and give our outfit an undeniably vintage feel. But for the most part, men don’t agree: “I don’t want to sound mean, but they honestly look silly and really dated. It takes her seriousness down a level. It makes her look like a little newsboy, like she’s wearing a Halloween costume.”

What to wear instead: Can we suggest not wearing a hat at all? Because if there’s one thing we know for a fact guys love, it’s a woman’s long, flowing hair. You could do long waves or a unique braid. Alternatively, if your outfit doesn’t look right with your hair down, try throwing it up in a messy bun – always cute and always practical.

Overly-Distressed Jeans

We’re not talking about jeans with a small rip on the knee – we’re talking about jeans where a good foot of fabric is missing from them, leaving a gaping hole: “These look ridiculous. Why would you pay for pants that look like you survived a shipwreck?”

What to wear instead: Let’s take a left turn out of the land of denim and into a totally different area: leather pants. We know, they’re definitely a look, but they’re one that guys actually really like: “These are cool. They’re unique but not trying too hard.”

Closing Thoughts

The guys won’t understand every fashion trend, and that’s understandable. But if you’d rather play things safe on a first date, we’d recommend sticking with classic wardrobe staples that have proven to be a hit time and time again, rather than going out on a limb and trying something too bold.

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