MENSWEAR2025
shopping my closet for winter menswear looks
This week I was deeply inspired by this interview with Aaron Levine. It was written in November and has been sitting in my inbox, unread until last weekend.
It is one of my favorite Leandra profiles to date, and I will tell you why. Aaron, a designer who recently released his first collection, is so vulnerable and open about the challenges, set backs, insecurities, and missteps he made along his way. I love this type of interview because it feels so authentic, and it feels like camaraderie. We all get where we’re going in a specific way, and there are inevitable moments where we have to rechart the course. And to see where he is now, after decades in the industry, is enough to make anyone believe the adage that “hard work pays off”.
Levine’s Instagram is a scrollable plethora of styled selfies, often times wearing something relatively simple but wearing it so well. I was completely inspired by his IG content, and by the way they shot the collection lookbook — so much so that all I’ve wanted to do this week is think about, shop about, and dress about menswear. I already have a menswear-leaning side to my style, but I’d say it’s gone untapped for a while now.
To honor my new obsession, I kicked off the week with a little menswear inspired thrifting to get the creative juices flowing. I only bought two pieces, but the creativity was engaged, and I knew I could 100% shop my own closet for the rest of the looks. It turned out to be really fun — I mixed and matched pieces that I’ve never even considered pairing, which is the ultimate goal of this “new lens” approach to viewing your wardrobe.
Let me just start by saying: you don’t have to be wearing *actual* menswear to get the menswear vibe. While I do have some vintage and thrifted garments that are technically mens, you can do a lot with reimagining womenswear pieces in new formations. Which brings me to the first look:
SHORT SCARF / LAPEL PIN / BIG DENIM
The vest is one of those aforementioned pieces that is actually vintage menswear. It’s a Sears Roebuck creation, flawless dark denim with front pockets, snaps, and a faux shearling interior. It has a bit of a bulky feel, but that’s what really makes it ideal to push the look into a menswear category. I found it at a local vintage spot (Biddeford Vintage Market if you are in Maine!), but luckily there are also tons of these on the vintage-net. Good search terms: vintage denim shearling vest mens. Here is a very similar one to what I’m wearing!
Other elements to this look: white crewneck tee layered under a rust colored v-neck sweater. Silver necklaces layered in between (over the t, nestled in the v), with a floral print scarf: twisted, double wrapped, and tied into a short knot. Any monochrome beanie / sunglasses pairing would work, but these are especially ~simple~ which I think is one of the unsung elements of successful menswear layering. The coup de grâce is the lapel pin, quiet in it’s placement but overt in intentionality. Something like this vintage 14k / diamond cravat pin (the pin to end all pins) would be one of those timeless pieces that quietly carries so many looks to the next level.
BOLO TIE / THRASHED BUTTONDOWN / TIED SWEATER
One quote from Aaron’s interview that I really liked was “I like to buy nice things. I like that! But then I like to beat the shit out of them, to really use them. Who cares if it gets a hole?”
This is so Maine to me! I grew up with some rough and tumble family members who would wear their clothes right down to the nub. As I’ve gotten older I’ve really come to appreciate this aspect of weathering and tempering your clothes to the tune of your unique lifestyle.
This next look is inspired by the sentiment that you can beat the shit out of your clothing and it will keep on getting better.
This is one of those looks I mentioned earlier — a combination of pieces I’ve never considered before, but thanks to my menswear-inspired mission this ensemble was born. It’s sort of a high-low mix of thrashed shirt with polished sweater. The sweater is vintage cashmere with a cool high collar in a positively vermilion shade of red. The bolo tie is a mediator of sorts, bringing a high shine gold/silver polish that is offset by a bolo’s innate rugged / rockabilly energy. Because layering really seems to be part of it, I also wrapped a grey cropped sweater (for the prudent among you, yes, it would have fit over the outfit) around my shoulders.
A quick tangent on jewelry to pair with your menswear vibe. A class ring is always a good bet (I’m wearing my mom’s ring). If class ring isn’t your thing, you can also go with a signet ring. I could spend hours looking at signet rings, there are just so many amazing ones out there. I highlighted a few great signets in my vintage jewelry post, but you can also get lost in the sauce via your own curated search. A couple to get you going: vintage class ring but w/o the giant gem, simple non-lettered gold signet, turquoise & sterling signet, or something totally unique like this zodiac signet (hey capricorn!) Chains and bolo ties also add a great dose of hearty metal, which is another way to lean into the MW vibe. This sterling bolo necklace is a really amazing mix of the two, but if you are leaning more towards something versatile that could be worn across many styles, a sterling rolo chain is just the thing.
THE ONE HIT WONDER
Sometimes all it takes is one garment to shift your look into a casual menswearsphere.
Two good ways to do this. #1 the bowling shirt:
I ran into this vintage silk shirt last year and knew ~on the spot~ that I needed it. It’s the color of lime sherbet ice cream, with a column of rich navy running up the buttons. Plus some navy piping on the sleeves for good measure. The casual nature of this shirt is great for the “just thrown on” effect — especially in the summertime.
and #2 the crewneck sweatshirt:
In my opinion, a crewneck sweatshirt is an essential garment for everyone. This was one of the pieces I picked up during my inspiration-thrift-quest earlier this week — I loved it from the moment I tried it on, and it was a low stakes investment at $5. In my closet you can’t really go wrong with a vintage crew sweatshirt. It goes with all the athleisure bottoms, it goes with jeans, it goes under jackets and over t-shirts. It’s a workhorse piece of apparel. Pop on a thrashed canvas tote in an offset color to bring it all together.
OLIVE & STRIPES
On the note of elemental colors, leave it to olive green to do the heavy lifting required to carry many a fall and winter outfit to fruition. This outfit is inspired by a person I once saw while grocery shopping — they were wearing a striped hoodie under an olive canvas jacket and it just ~worked~
A look like this is really easy to throw together as long as you have the basics — that is, the olive and stripes. Once again the white crewneck tee is a perfect pallet to begin the look. Adding a string of beads creates textural interest between layers. I actually made this necklace myself at a beading workshop in Portland (so much fun, hey @caravanbeads!) and it’s the perfect strand for a subdued ensemble like this one.
The outerwear is an extremely vintage military jacket that I got ages ago in Portland. I’ve always held onto it because details like the classic snap enclosures, front facing pockets, and quilted seaming are not so easy to come by. Here’s a cool vintage military jacket — different overall design but would give a similar effect. The inner layer is a double knit cotton sweatshirt from LL Bean. It’s got an essential boxy shape that I love, and the navy/cream stripes are the ideal androgynous pattern. Some cool ones out there right now: 100% cotton French terry, oldschool Gap in another classic colorway, and one that looks good for layering.
A couple of other accessory recommendations: a warm neckscarf (love the way a short bandana scarf can be prominently knotted, here is the cashmere version I'm wearing), plus clean & simple sunnies (I don’t remember where these sunglasses came from, but I-SEA is my favorite spot for affordable and stylish frames. Here is a great black option). Also the ever utilitarian fanny pack (mine is flowfold, closest thing they have now is something like this).
BANDANA / BIG SWEATER / DAD HAT
This last ensemble actually produces 2 different looks — both embodying that masculine (or perhaps just not overtly feminine) energy. It’s another example of a really simple formula that, when crafted intentionally, works again and again.
This white tee won’t quit! Here she is again as the base layer, styled under a fitted sweater vest, with silver chain layered under a divinely aged bandana. Plus a mens wool sweater (vintage abercrombie & fitch from my fall essentials edit) tied at the waist.
V2 of this is to actually don the sweater, paired with the now-ubiquitous dad hat. I think I’ve mentioned before, but about 5 years ago I lost my only pair of sunglasses, and in a bout of laziness I didn’t replace them for the entire summer. Instead, I wore a brimmed hat every single day. After that I simply can’t be in the sun without a brimmed hat. My head gets hot, the sun beams down the top of my glasses, my scalp gets burnt…I just can’t! And while I started out wearing the classic brimmed summer hat, I eventually turned to dad hats and have now amassed quite a little collection. I can’t say enough about how easy and comfortable this outfit is, while giving off an effortless cool.
Well, that sums up my headspace for the week! It was so energizing to chase this rabbit and feel the thrill of getting dressed differently. Many of these pieces are ones I have had for years, or ones that I’ve worn on repeat in some other ensemble, but to breath new life into them via a shifted perspective was so much fun.
Here’s to finding your own rabbit — in whatever facet of life — and enjoying the thrill of the chase.
xo, Georgia
Soooo gooood G! I don’t know anyone who can make those look as chic as you. Menswear is some of the only good thrifting left out there imo!