Fashion for me has always been more than just getting dressed—it’s a way of showing up in the world as the fullest version of myself. My current style (because it’s always evolving) leans into cozy vibes with a touch of Scandinavian polish—maybe the Danish girlfriend effect—but I’ll never completely leave behind playful colors and bold pops that make an outfit feel fun.
I’ve also been obsessed with anything embroidered or customized. Personalization is such a cool way to make clothes feel unique to you—whether it’s chain stitch details, a custom embroidered dress shirt, bag charms or even someone you love’s initials on your hat. It can get expensive quickly, but if it’s within your budget, these little details take style to another level. And honestly, the best “personalization” you can invest in is finding a good tailor in your neighborhood. Well-tailored clothes will change your life.
Fall and winter are my favorite seasons for experimenting because layers not only keep me cozy but also help me feel more confident in my body. So here are 12 pieces I’m excited to add to my masc fashion wardrobe right now.
The Oxford Shirt (with a Twist)
There’s a reason Oxfords are a staple—they’re endlessly versatile. I love using them as layering pieces under sweaters, cardigans, or even crewneck sweatshirts when I want a clean, classic look with some dimension. They’re also perfect on their own with a pair of jeans, especially when styled with the right shoes and accessories to pull everything together.
Right now I’m especially into the Amazon Essentials Oxfords. They’re about $20, and the quality has really impressed me. In the early fall, I wore them open over a t-shirt with shorts or linen pants for an easy, relaxed vibe. Now that the weather is cool, I’m layering them under heavier pieces. For me, a more classic fit (not oversized) feels just right—it layers better and keeps the look sharp without being fussy.
Classic Dad Hats
My hat style has gone through every phase—five panels, A-frames, truckers—but this fall I’ve circled back to the timeless dad hat. What I love most is how versatile it is: I can throw it on for a coffee run and look casually pulled together but it also pairs surprisingly well with a sweater giving the outfit a polished, almost classy feel.
Lately I’ve been living in a classic navy blue Yankees cap. There’s something about it that feels a little more “dressed up” than the Nike hat I’d usually wear to the gym. For fall, I grabbed a corduroy version that I’m absolutely obsessed with—so much so that my girlfriend and I argue over who gets to wear it on the weekends. The beauty of dad hats is that you can find one in almost any color, team or brand, but the simplicity of the Yankees cap has me hooked right now.
Pleated Pants
I’m fully in my pleated pants era right now. The pairs from Dockers and Urban Outfitters are my current go-tos because they add this fun old-school vibe to any outfit. I’ve been especially into mixing them with more casual tops—it’s that same energy as pairing loafers with running shorts. Not for everyone but I love the contrast.
Plaids and textured fabrics are where pleated pants really shine for me—they feel vintage without trying too hard. The only thing I’ll say: pleats do draw a little attention to the hip area. If that’s a part of your body you style around (like a lot of AFAB people with curves) it’s something to keep in mind. Different brands cut their pleats differently so it’s worth trying a few until you find the ones that fall just right for you.
Cozy Oversized Cardigans
For me cardigans only work when they’re made from a thicker, weightier material. The slimmer, thinner ones tend to cling to your body and feel dated—not my vibe at all. A looser fit with some structure instantly looks more flattering and modern.
I like to play with both classics and statements here: a solid chunky cardigan can ground an outfit, but I also love when there’s a fun pattern or unexpected color. Layering is where cardigans shine—over a tee under a coat or even paired with a collared shirt for that dressed-up/dressed-down balance. And if you can find a cropped version? That’s even better. It adds some shape while still keeping that cozy, relaxed feel.
Thermals and Henleys
Thermals and Henleys are another layering essential for me. I have a couple of simple ones from Hanes that I’ll toss under a t-shirt on a cool day, and I love the versions from Uniqlo when I want something a little more polished. They’re versatile—you can dress them down with joggers or sweatpants,s or make them feel like a cozy Sunday morning outfit by pairing them with nicer pants.
If you can find a waffle knit + henley combo that’s my idea of the ultimate casual-but-put-together fall fit. It feels effortless like channeling my 90’s dad vibes—just pop me straight into a cozy episode of Gilmore Girls.
Retro Fleeces
I’m big on retro fleeces right now—the true fleece not the shaggy teddy-bear kind. I like them a bit oversized, especially if they have elastic or a cord to cinch the waist. That boxy cut with a collar is exactly the look I’m going for.
I love when fleeces come in fun prints or bright colors, but I’ll never say no to the easy wearability of classic tones. The key for me is avoiding anything that feels too much like technical hiking gear. I want mine to feel casual and city-ready—more Nike, Patagonia or North Face lifestyle pieces than something you’d wear to summit a mountain. And of course, you can thrift amazing options. A couple of my favorites actually came straight out of my dad’s closet.
Statement Tote Bags
I used to think of totes as a necessity—because honestly, I hate having my hands full and I can’t stand the look of overstuffed pockets. But somewhere along the way, they shifted from being purely practical to becoming one of my favorite parts of my style.
@hellofromniko My @llbean bag tour! ✨ After a year or so of customizing my bag, I feel it’s time to share all the things I’ve added/done! #llbeantote #llbean #chainstitch #chainstitchembroidery #diy ♬ Refreshing and light indie pop(1552207) – Cheng Lee
There’s something I love about romanticizing the little moments: coffee in hand, tote over my shoulder, ready to pop into a farmer’s market if I stumble across one. People are also customizing their totes in such creative ways right now. My favorite inspiration comes from Nico on TikTok—he’s done some really cool takes on the trend.
And for the dog parents—this one’s for you. I found a tote that’s specifically made to carry my 14-year-old dachshund, and it’s a showstopper. Every time I take her out in i,t we get compliments. It’s both functional and stylish, which feels like the perfect summary of what I want my wardrobe to be.
Running Shoes (Trail-Inspired Please)
Nothing ruins my day quite like uncomfortable footwear. I’m approaching 40 let me live! A good running shoe is essential but lately I’ve been most into the styles inspired by trail shoes. They’ve got that sporty outdoorsy edge but still work seamlessly in city fits.
The Toga Pulla x Asics collab has been on my radar and of course the Salomon XT-6s are still cool (and everywhere). But for me it’s less about hype and more about comfort paired with that trail-running vibe. Maybe it’s because this fall is marked by one of the biggest adventures of my life—trekking to Everest Base Camp—which has had me doing plenty of walking and hiking in the lead-up. Either way a stylish running shoe feels like the perfect blend of my day-to-day city life and the big adventures I’m chasing.
Loafers for Everyday Cool
Loafers are one of those pieces that make me feel like I’ve leveled up an outfit without even trying. I’ve been especially obsessed with T-bar loafers lately. Corridor (if I could do all of my shopping there I would) and GH Bass have some amazing versions but at one point I think I would’ve sold my soul for the Adrian T-Bar Loafers from Doc Martens. They’re unique, versatile and give that perfect blend of polished and playful.
For everyday wear I love my Doc Martens tassel loafers and the Clarks T-bars. They go great with jeans and can occasionally be styled up with dress pants but one of my favorite ways to wear them is with shorts and socks. It’s not everyone’s vibe but I think that mix of preppy and casual feels so good right now.
Loose (But Not Too Baggy) Jeans
When it comes to jeans I don’t want anything cuffed or overly styled—I just want a clean classic fit that works every time. Abercrombie has been a go-to for me for years and when it’s not them it’s always Levi’s.
Right now my favorite fits are the Levi’s 565 Loose Straight and the super-classic 550. I’ll die on the hill that the 550s will always have a place in your closet no matter what year it is or what the trend cycle says. They’re comfortable and reliable and they strike that perfect balance of loose without being sloppy. For me these are an everyday staple—something I know will look good with everything from hoodies to loafers.
Heavyweight Hoodies
A heavyweight hoodie is one of those wardrobe essentials you can never have too many of. The quality makes all the difference—thin hoodies just don’t cut it for me. I want something substantial that holds its shape and layers well.
Abercrombie makes some great ones and Elwood has been another go-to brand. But I also have a soft spot for the retro collegiate vibe of the Champion Reverse Weave hoodies. They’ve been around forever and for good reason—they’re durable and cozy and they give me that nostalgic throwback energy. Whether I’m layering them under a fleece, pairing them with jeans or just throwing one on for a coffee run heavyweight hoodies are the backbone of my cold-weather wardrobe.
Sweaters with Fun Prints
Sweaters are where I let myself play the most. I love fun prints and unexpected colors and you can find some great options everywhere—from Bershka and Zara to Scuffers or the thrift racks. The key though is in the fit. I want them oversized but with some intention.
If the sweater is cropped or has a little structure at the bottom it works perfectly on its own. If it’s longer and looser then I balance it out with straight-fit pants instead of something super baggy. That little bit of balance makes the difference between looking cozy and looking swallowed by fabric. A good sweater like this becomes an instant statement piece while still being easy to wear every day.
Bringing It All Together
There are a million ways to be a stylish masc and this list is just what’s exciting me right now. My wardrobe is always evolving—right now it’s leaning cozy with some Scandinavian polish (thanks to my Danish girlfriend), but playful color and bold statement pieces will always be part of my vibe. At the end of the da,y style is about feeling like yourself. For me that looks like cozy mornings working from home, coffee + pastry runs in NYC, nights out with friends and plenty of dog mom moments along the way. The best part of fashion is making it your own and letting it shift as you do.
