Is Showing My Ankles Really a Fashion Crime?

Dear Allison,

Gen-Zers on TikTok are saying some of my fashion choices are “cringe.” Is it really a crime to show my ankles?! Please help me navigate these uncharted waters. I don’t want to be perceived by baggy jean-wearing, Labubu-carrying college kids. 

Sincerely, 

An aspiring cool millennial 

Hi fashion friend,

First off, from one millennial to another, I’m sure you look a lot cooler than you think you do. Second off, try not to get too wrapped up in this internet conversation about what is considered “cringe” and what is not. We all know trends are cyclical, things go in and out of style all the time and that’s just the way the fashion industry works. But I don’t think that means we should always be striving for timelessness — it’s pigeon-holing us.

I have so many clients, especially older clients, are scared to try new things or participate in trends because they don’t want to look back and feel embarrassed by their past selves. And to that I say, who cares! There is something to be said about looking back at photos of your past self and thinking, “I wouldn’t wear that today but I remember loving that look at the time and feeling really good in it.” Taking risks is a really important part of discovering your personal style and making sure it evolves over time.

The phenomenon of getting dressed for your phone or for social media is also quite limiting. If you know that photographic evidence of every fashion risk you’ve ever taken is going to live on the internet forever, you might be more likely to play it safe. My advice is to free yourself from your phone and the potential judgement from your future self. Live (and dress) authentically, as lame as that sounds. And for the record, trying is not cringe at all. There is a lot of effort and styling that goes into achieving that effortlessly cool look. If you don’t try new things, you’re never going to move your style forward in any way. You need to evolve and try and the only way to do that is to throw things at the wall, sometimes it sticks and sometimes it doesn’t. Trying and failing is the only way to be modern with your style.

All that being said, let’s talk through some of the fashion trends Gen-Zers hate the most. Keep scrolling to read my hot takes on everything from showing your ankles to having a going-out top, as well as my style tips for making each piece feel more modern and less cringe.

The Myth: Wearing ankle boots is cringe.

The reality: I agree that wearing cropped jeans with ankle boots is not a good look. But not because it’s cringe per se, more-so because it cuts off the legs and throws off the proportions. You can totally still wear ankle boots, despite what Gen-Z says, just make sure you style them with pants that have a longer hem. The goal should be to have your jeans cover the top of the boot, even when you’re sitting. Wearing pants that pool at the bottom or maybe even drag a bit (if you don’t mind that) will really modernize the ankle boot and make it feel less cringe. I think that’s the key for every “out” piece; it’s not really the piece itself, it’s the styling of it.

The myth: Showing your ankles in general is also cringe.

The reality: If you’re doing a mini skirt and loafer with no socks, that’s fine! I don’t mind showing ankles in that way. I think what becomes somewhat awkward-looking is when you show your ankles with something cropped that hits at your calves — whether that be a pant, jean, skirt, or dress. When that little strip of skin between the hem of your pants and your shoes is showing, it’s usually not a great look. Wearing a cute little sock like these from Comme Si can help because, even though you’re technically showing your ankles, it feels more intentional.

The myth: Doing a French tuck is cringe.

The reality: I don’t think this is cringe but I think the word “tuck” throws people off, especially older people who think it has to be a very deep tuck. They get confused about what to do with the material hanging out on the sides. Instead of shoving as much of your shirt into your pants as you can, tuck in an inch or less of fabric behind your belt buckle and then let the rest of your shirt fall forward. It’s not a full, dramatic tuck. It should look and feel effortless. If you’re still unsure about what constitutes a cringe French tuck versus a cool one, think of it like this: you want the tuck to show your belt buckle or pant button and the two belt loops that are closest to the button – nothing else. The draped silhouette that can be achieved with a loose tuck is stylish but if the tuck is too deep and precise-looking, Gen Z might call you cringe. You should be aiming for a fold, not a full tuck.

The myth: It’s cringe to have a going-out top.

The reality: Hell no. Having a going out top is not-at-all cringe. Who doesn’t want a sexy top to wear? Maybe it’s not the vests or corset tops of a few years ago, but there were deep V-necks, sheer tops, and slinky tanks on the runways this season — and those all make great going-out tops. A vintage silk camisole from Etsy, for example, is cool right now even though it’s something I would’ve worn in high school. Instead of styling it with skinny jeans and ankle boots, I’d wear a wider pant or a trackpant trouser to make it feel modern. Whatever you think of when you think of a classic going-out look, just rework that a bit. It’s all about taking your “dated” pieces and using them in a different way. The fashion industry wants you to think it’s the piece itself so you buy more stuff. But really, you don’t need new stuff, you just need to style your stuff in new ways.

The myth: Wearing tight workout clothes is cringe.

The reality: Not cringe. But I do love the idea of moving away from leggings and fitted workout tops in favor of track pants, wider sweatpants, or wearing a big funnel neck windbreaker or a vintage Champion crewneck sweatshirt with leggings instead of a tight top. But I still think it’s totally acceptable to wear a tight workout outfit.

The myth: Side parts are cringe.

The reality: I still like a side part, I don’t think it ever went out of style. When it comes to hair and makeup trends, it’s not about cringe versus cool, it’s about which ones look best with your face shape and bone structure.

The myth: Fitted motorcycle jackets are cringe.

The reality: Leather jackets are timeless to me. So many of my clients want to know if they should get rid of theirs. If it’s a nice one, my answer is no. It might be considered cringe to style it with skinny jeans and ankle boots but wearing a motorcycle jacket with a gray sweatshirt and big black trousers feels cool to me. If the jacket is cropped or fitted, wearing it with oversized pants will make it look more current. Even if the silhouette of yours feels dated, hang on to it because trends are cyclical and you’ll probably be able to wear it again in the future.

— Your fashion friend, Allison.