Regressing with Vintage Sweatshirts, Hoodies, & Sweatpants


Up until college, I wore hoodies and sweatshirts all the time. Suddenly, I cast them away, finding them lazy and illfitting for a gentleman in tailoring.

Then after years of breaking that cringey mindset, I find myself wearing them again, this time with a new mentality and method that would have melted 2013 Ethan’s Gatbsy-loving brain.


Most of the menswear guys I know have been tailored guys through and through, even through their youth. They’re mostly preps or vintage-enthusisats and they knew that they were going to look sharp for most of their life. Others were ex (or closet) punks who still looked cool and had great style, despite not wearing a tie and soft tailored jacket until much later in their evolution.  I was neither of those things.

I dressed like a  very stereotypical nerd for most of my life.  Yes, I started to get into vintage style (not done well, mind you) when I watched The Great Gatsby and Gangster Squad, but that didn’t happen until 2013 (my freshman year of college).  So until that happened, I was in graphic tee shirts, baggy jeans (or the dreaded plaid shorts), and hoodies.

I wish I had more pictures of me in high school wearing hoodies, but this is what I got.

Hoodies and sweatshirts were my jacket of choice for the late 1990s and most 2000s. It was a time before H&M, when most clothes  weren’t made with design  (or general coolness) in mind.  I even had that mindset of “I’d rather spend my time focusing on school (or video games) rather than think about fashion”.  To me, “cool clothing” came when you were an adult, so I was okay with looking very schlubby all the time. Very cringy, but hey that’s who I was.

To me, the hoodie (and by extension the sweatshirt) seemed to be the ultimate piece of utilitarian wear. It keeps you warm, can protect you from the elements, and can literally be thrown on with anything. It also wasn’t as dressy as wearing a sportcoat or as heavy as a peacoat; I had no way to get a leather jacket back then and hadn’t even conceived the notion of what a chore coat was.   All of my hoodies and sweatshirts were related to something external, like high school merch or something from a family vacation, making them quite like a graphic tee shirt in that regard.

Plus, it seemed everyone wore one, form the nerds to the cool guys.  Sure, most were big on my frame (I’m kind of a small guy), but who cares! It was literally the outerwear of choice for everyone. You can blame countless young adult culture protagonists who rocked the hoodie and shown that you can still have a great life, get the girl, win the competition, etc.  Who needed to dress up?

Then I got into vintage and (classic menswear) and my entire world changed. I saw that it was great to use clothing to express your style.  That suits could be comfortable.  That there was more options to casual wear than just sporting a tee and hoodie that were just as natural and easy to wear! I cast out (nearly) all the hoodies and sweatshirts that I wore in high school and early college and never looked back. Until I met Doug.

Doug should be familar to you, especially if you’ve payed attention to the blogs over the past year.  He’s lived near me was actually a reader of my blog, which is how we soon became good friends.  While he’s not exactly a tailored type of guy, Doug appreciates good suits and classic style.  However, his main focus in the form of Americana: selvedge denim, rugged milsurp jackets, and you guessed it, vintage sweatshirts and hoodies.

I always thought he rocked the look and while I did adopt certain elements (Spencer took to it right off the bat), there was something holding me back. Maybe it was because I distanced myself so much from the old hoodie wearing teenager!  Maybe it’s because for a long time, a hoodie = lazy in my mind.

But the more I hung out with Doug, saw how he wore them, and learned the details he sought after, I started to see those pieces in different light. The way he wore sweatshirts and hoodies was so different from anything I had seen before; it was also probably the first time I really saw the garments worn in general (outside of regular people on the street) since I had been engrossed in tailoring for a long time.

So now here we are.

Vintage Sweatshirts

The reason I like vintage sweatshirts (or ones made in a vintage style) is because they follow what I love from vintage sweaters: they fit close to the body, have great details like wide ribbing, and (perhaps most importantly) they were cut for high waisted trousers.  Hoods were meant to fit close to the body and not make you look like a Sith Eternal cultist when worn up or to hang haphazardly on your back.  Also, these sweatshirts were almost always made from cotton (with a few polys thrown in in later decades) making for something sturdy, yet soft when broken in naturally. The more I saw and learned, the more began to notice the familiar comparisons to the knitwear I already enjoyed wearing!

In addition to being different in terms of silhouette and ribbing, they also simply were designed differently and featured some other great details. Two tone coloring is a big one (since common sweaters were white or grey) but what I latched onto were the deviations from pocket details, like patch pockets or handwarmers.   Even half zips looked markedly different than the ones WASP dads wear!

These fun details (as well as the silhouette) remained customary across different sweatshirts until the late 80s when oversized became en mode. No longer did we have wide ribbing, a close fit, short length, and cool details.  That’s why guys like Doug are heavily into vintage ones and when they wear it, it doesn’t look like a typical hoodie.

Perfect tailored proportions on these sweatshirts and sweatpants!

Seeing old photographs and illustrations of vintage sweatshirts also helped reconcile it in my mind.  The guys wearing it didn’t appear to be ultra-grunge, super hype, or even come off slightly athleisure.  To me, vintage athletic wear literally looked like an extension of tailoring.  The sweatshirts all end right around the waist, similar to a normal sweater or a short jacket; even the sweatpants were cut high in the waist and straight in the leg, without breaking too far over the shoe making them very similar to a classic pair of chinos or denims.

The overall style is very Americana, with hints of ivy and workwear mixed in. Some sweatshirts were plain/colorblocked while others have emblems and stamps to show where they were from, differentiating them from more dressy sweaters. Even though the guys in the photographs wear it without care, they still look more put together than a regular dude off the street. It doesn’t come off as too slouchy or too over-the-top, which was my original attitude to sweatshirts and hoodies. Maybe, just maybe, I could wear it too and make it a intuitive addendum to my wardrobe, worn to things like Flea Markets or Quarantine at Home.

Vintage ones can range in price from $30-100+ contingent on where you’re shopping and the details while reproduction ones (like LVC or other vintage-inspired brands) are usually $200+, justified since these style of sweatshirts are not really popular anymore.  So it really depends what you’re looking for!  I will say that I’ve only found them at flea markets and dedicated vintage sellers and have never come across them at regular thrift store.

Polyester blends are fine, but beware the ones with heavy fleece on the inside or the ones that utilize a mesh-lining. To me, they’re uncomfortable and wear too warm for Los Angeles.

Smaller head opening and hood make for a “snug” appearance. This is also why you find vintage ones with tears in the neck placket-area for this reason: people eventually tore it the more they wore it!

Great ribbing, coloring, and pocket details.

Handwarmer pockets on the right! Insane.

Two tone is epic.

Patch pockets.

Love the ribbing and wide collar. Evokes great tailored knitwear in that regard.

Raglan sleeves are a nice touch, whether it’s on an overcoat or a simple grey hoodie.

Looks ivy right here.

Obviously, hoodies, sweatshirts, and sweatpants never left the lexicon of men’s fashion, but they became something shunned   It was almost shameful (like to menswear youtubers) to be seen wearing it! However, some places of fashion kept it alive and stylish.  Streetwear is an obvious one, but as I kept exploring my tastes and meeting new people, I began to see how it was worn by Americana-ivy enthusiasts, particularly the Japanese. Nothing against, the athletes of old, but it’s nice to get some new forms of inspiration.

Their use with tailoring or “smart-casual” can be a bit dissonant for conservative dressers, but to me it seems cool as hell; as the kids say, it started hittin’ different.  It’s not quite as “smooth” as athleisure but certainly not as louche as say Italian Riveria (loops collars and jackets) looks.  There’s a sense of utiliarianism that is also subversive, similar to why I like wearing berets. Overall, this mixture of classic clothing with unconventional pairings fits within the way I approach my style! To be clear, I wouldn’t wear this stuff exactly how it’s being presented, but it definitely got me thinking.

Anyway, just had to say big ups to the books and magazine I bought during my Japan trip, since they offered up the best inspiration!  Again, who would’ve thought that hoodies and sweatpants had a place out side of a lazy sunday or the gym?

And yes, I am clear that Simon Crompton has written about hoodies before (here and here), but I felt that I wanted something that wasn’t as “refined”, despite my want to make the sweatshirts (and related accoutrements) work within my love of ivy.  

Kinda skate style but also kinda ivy.

Definitely more skate, but cool!

Fun LVC reproduction, but oversized.

Tweed raglan overcoat and hoodie? Fine for me.

This seems very new york to me. Also, the hoodie + coat is a very women style thing, but can be applied to menswear.

OCBD and sweatpants.

If Simon can do it, certainly I can too?

On Friends

Before we get into how I wear them, let’s look at Doug, who has spent a lot of his time collecting vintage sweatshirts (among other vintage grail pieces). He would sing their praises to me each time went picking and note to me all the details to look out for. Things like labels, the horizontal stitch on the pockets, and of course the ribbing, became new details I would look out for when hunting.   Of course, he would look for other things, like specific colorways, stamps, and distressing (fades/tears).

Sweatshirts are really his base layer of choice, as he’s worn all varieties (crewnecks and quarter zips) each time I’ve seen him. He doesn’t just resort to looking like a 1950’s athlete, instead combining these pieces with different military chinos and denim jackets to create a wholly Americana rugged-casual look that isn’t sloppy or dressed up (resorting to ivy).  With all the big fits, layering, and proportions, it wasn’t hard to see its similarities to some aspects of modern streetwear, just with some pieces swapped out. Does that approach sound familiar?

Faded salmon is a color that everyone lusts after.

Quarterzip with a point collar and dropped shoulder seam.  A bit analagous to modern oversized sweaters and certainly much cooler than the zips your dad wears.

An example of a rare army stamp sweater. Look at the cropped body and wide ribbing!

Ripped neck area (among other things).

A couple of Doug’s favs.

Brian Davis of Wooden Sleepers also dresses similarly.

College sweatshirts are common and incorporate that true school ivy charm without resorting to the varsity letter wool sweaters you typically see.

Keith is also a big seller of great sweatshirts.



Quarterzip looks less “dad” with a Lee westerner and silverbelly fedora.

My other main source of friend inspiration comes from John Robinson, yet another reader of the blog turned compatriot in the Facebook group. Like Chase and Dick Carroll, I think John is one of the best guys out there for his true (yet individualized) approach to classic ivy style.  With the sack jackets and flat front (plain hem) chinos with white socks/loafers, his posts always get me amped to go ivy.

His overall style deserves its own blog post, but I’m including him here for his use of sweatshirts/pants with ivy tailoring.  It’s just so insanely good and cohesive, despite being incongruous to all rules of formality.  To me, it looks exactly if a university student in 1961 dressed up today, wanting to look sharp but also utilitarianly casual.  There are probably some aspects of Japanese-Americana influence here as well. And it doesn’t look too “try hard”, at least to me.

It’s also important to note that his sweatshirts and hoodies aren’t vintage, and as a result, lack the close fit and short length of my vintage pieces, but that’s okay. He tucks them into high rise trousers, and appearance is much cleaner! The fact that he always wears a layer over the sweatshirts also help to hide the baggy fit.  It’s worth exploring if you aren’t able to source vintage ones! Just makes sure your jackets aren’t too snug; this is why he prefers the slightly boxier cut of a classic sack-jacket.

After Doug provided the rugged workwear/milsurp inspo, I needed to see Doug’s refined method without just being worn with an overcoat, as most people tend to do.

Modern sweatshirt (hence the tuck) but looks so good here with a camel sack jacket.


I don’t think I’ve seen a hoodie look so good with a blazer. Note the tuck.

Even the use of sweatpants is next level.  If only college kids did this! 

My Pieces

After all this (especially vintage picking with Doug), I decided to get some for myself and incorporate them into my wardrobe.  Honestly, at first, I only used these sweatshirts to work out in, as I didn’t really see it fit into my casual style very well.  But like most things, it just took time for me to get inspired and bring it in gradually in a way that made sense naturally.

Ultimately, I just had to make an outfit that I was proud of an felt authentic in order to remove the “lazy” connotations that most menswear people have toward sweatshirts, hoodies, and sweatpants. And despite a sad time being stuck at home lately for quarantine, I actually like how it’s offered me the opportunity to experiment and find my own interpretation, especially after considering all the inspiration I’ve laid out for you above.


The first vintage sweatshirt I had was the quintessential grey one, sold to me by Doug for about $60. I’m not sure exactly of the age, but it seems to be at least from the sixties, as it follows all the details that I looked for: wide ribbing, dropped shoulder seam, extended horizontal pocket stitch, and a small head opening/hood. It’s a feels a bit on the tough side (especially after a wash), but it loosens up after repeated wears.

The condition isn’t the best, containing just a few stains at worst, but because it literally is a piece of athletic wear, I’m surprised it isn’t as ratty as the others we featured in this article.  I do like the use of a frog patch on the pocket to cover up the hole, which only adds to the fun of the garment since it’s just the typical heather grey.

Because it’s the classic color, it really goes with everything that a classic grey crewneck sweater would go with (which is everything); it just has a hood!  I already knew it looked fine on its own with jeans and sweatpants, but I liked the challenge of making it a bit more “tailored”.  I wasn’t about to wear it with pleated flannels and a hopsack sportcoat, but the hoodie seemed to be just fine with low-key stuff like paint splattered chinos and a chore coat (which are my alternatives anyway).




Gotta get the most wear out of your stuff!


Navy blazer and HBT work pants. Definitely pulling together Doug and John here.

After wearing that grey one for a few months, I since have obtained two more hoodies: one in a bright light blue from a flea market seller and another in a faded purple (but not quite lavender) from a random used clothing store (not a Goodwill) in DTLA, for about $30 each! The details are largely the same, with a few changes here and there (one has raglan sleeves, the other lacks the horizontal pocket stitch), but they get the vibe across.  Though I will say, these other ones are much lighterweight and softer than the grey hoodie, making them more easily worn here in Los Angeles. Provided that I could work around the bold coloring.

It’s been fun to wear them and create different casual looks that brings everything I love in ivy and workwear-milsurp together. My only rule with them is that I try to use them like Doug and John: a base layer. That means I don’t wear it on it’s own, opting to pair them with some sort of jacket to make it more interesting.  I also try to wear them with non-jeans for that same reason.

I think it works well and looks good due of the silhouette. It doesn’t look like the ones I wore when I was a kid! Could be the close fit, but it could also be because it’s cropped shorter, so it works with a classic high rise trouser.


Raglan sleeve!


Hoodies are perfect to layer with chore coats and chinos of all kinds!

A bit of fun with a navy DB jacket and sweatpants. More on the latter later.



The vibrant blue is hard to match, but fine with solids.

Layering with a down vest is one of my go-tos other than just a chore coat.



Spencer in a 1950s white hoodie, layered with a bomber.


While hoodies are fun to throw on, I felt that I was missing the ease of a full-zip model.  Don’t get me wrong, I like the hoodie, but it always felt a bit too athletic for me; the fact that it literally covers up any thing you’re wearing underneath was also bugging me.  I guess I likened the hoodie crewneck and the full-zip to a sportcoat.  YMMV.

Luckily, I didn’t have to look very far for one, as a seller at Inspiration LA had a box of sweatshirts for $10.  They weren’t as cool or rare as the others I’ve seen before, but I was able to find the lone plain navy zip hoodie (without the scratchy poly mesh lining)that fit me decently! With it’s soft feel, semi-wide ribbing, and cropped length, it really was the perfect one I was looking for.  It reminded me of the ones I wore in high school (since navy was our color), but in a way that actually fits me.



You can see in the pictures above that the fit is largely similar to the hoodies I’ve worn before: a bit slim through the arm and straight through the body. To some (like my dad) it looks like I bought a size too small, but trust me when I say that I think it’s perfectly fit and proportioned for what I was looking for.  I mean, as long as it isn’t too tight and ends at my natural waist it’s good for me.

I actually haven’t worn it too much apart from throwing it once I’m home, but I have worn it a few times with an OCBD and tie.  The fact that I can zip it half-way or simply leave it undone to show off what I’m wearing underneath puts it in a different class of sweatshirt than the regular hoodies. Whenever I wear it, it definitely looks a bit like a “cool teacher” or 500 Days Of Summer, and I love it.  Undoubtedly strange, but it provides that youth-ivy look that I enjoy.  Easy going (especially with smarter pieces) without leaning too far into streetwear or that milsurp/workwear look.

Kind of a skater look.

After buying a few vintage sweatshirts, I was suddenly inspired to raid my family closets. I knew that the ones I’d find wouldn’t be in the same details or proportions as the ones I had picked (my family moved to LA in the late 80s), but finding ones from my childhood would be fun! It would literally have that same charm as those college/military stamps that Doug and his compatriots would love so much, except it would give me a personal connection.

The first I unearthed was a green hoodie from Astrocamp, a science excursion my 6th grade class attended for a week. This is unquestionably a mid 2000s sweater, since it’s a a bit baggy (marked a size 38, I don’t know what my little boy brain was thinking) and has heavier feel.  I love the color, but it really isn’t the best for the vibe I’ve gone for with my other sweatshirts.

It’s since been relegated to be homewear (washed a few times since I don’t know when it was worn last) but it’s fun to wear out for low key (read lazy) hangs with friends. I especially like it with my down vest, since it’s much too large to fit under a chorecoat.

Fall color palette!


Astrocamp hoodies and a bad movie.




Raglan sleeves!

The other sweatshirt I found was my dad’s old University of British Columbia sweatshirt, from the early 80s. Unlike the Astrocamp one, this one is incredibly soft, marking it very similar in texture and touch to the vintage hoodies.  My dad is larger than me, so this one is also big, but it looks good tucked in! I’ve always wanted to find a vintage college sweatshirt and I’m glad this one fulfills that, as well as providing that fun personal connection.


This brings us to crewneck sweatshirts. I actually don’t have many vintage ones, not just because they’re rare/expensive, but because I’d rather just wear a crewneck sweater with most of my outfits rather than a sweatshirt since they’re dressier.  However, that didn’t stop me from looking for them (vintage or contemporary) as I’ve journeyed around.

The first real one I got was from Ebbets Field, purchased during my trip to Seattle with my ex-girlfriend two years ago. It’s got the prized wide ribbing and front triangle cross stitch that many pickers look for, which results in a fun vintage look, especially with the Fuji Athletic Club logo. The sweatshirt was on sale, so I bought it!

Wearing black within classic menswear is something I love, but I admittedly don’t wear this sweatshirt very often. It’s soft but heavy in weight, due to it’s looped terry cloth fabric. It take it that it’s meant to be worn on it’s own (bare skin) instead of layered with other pieces, which makes it a bit hard to wear. Nevertheless, it’s nice to whip it out on occasion.



Faded salmon J. Crew hoodie I got in my early years of college. Nothing really to write about other than it’s my version of the expensive ones that Doug and other Vintage Pickers like to wear.



Cutoff sleeve sweatshirt made as a JFK health initiative before his assination.


Of course, one of my grails was the quintessential grey crewneck sweatshirt, and boy was I glad to finally get one.

Purchased from a vendor at Zebulon Bazaar, this sweatshirt is a 60s 50/50 one that hits all the right notes: super soft/lightweight (more so than the purple/blue hoodies), cropped length, and wide ribbing. I didn’t care that it lacked the traditional triangle stitch at the collar.

There doesn’t appear to be much distressing (only the ribbing has some holes) so it actually works well for super-casual fits as well as slightly dressed up ones (aka ivy).  It’s probably the most perfect sweatshirt I own since it’s so incredibly versatile. Before this, I had a couple of modern ones from GAP or J. Crew that were too long for high rise trousers, not the right shade of grey, or just too heavy to worn much.

Older vintage ones tend to be much more expensive, distressed, or both, so I’m very happy I got one for only $40! Definitely going to be wearing this until it literally falls apart.




Grey crewneck sweatshrit and military chinos are a GOAT combo.



Spencer’s taller frame works for modern sweatshirts, and he wears his grey one a lot.



I would be remiss if I didn’t talk about the quarter zip sweatshirt. Like I’ve alluded to earlier in the article, I always recoiled at these since they looked like legitimate dad wear (and  I don’t mean dad-core).  It could possibly be due to the fact that most quarter zip sweaters featured a standing collar, which I definitely have an aversion to; it’s the reason I don’t like Valstarinos, Baracuta G9’s, or M-65 field jackets.

However, as you saw on Doug, vintage quarter zip sweatshirts had point collars, which appear to be like a sportcollar.  That was all the information I needed to reconcile it in my head, so when I found one for $45 from a Rose Bowl vendor, I didn’t hesitate.  I love the off white color as I consider it more versatile for my style than the blue one that Doug has. Most ones I’ve seen tend to have some sort of stamp or logo, so I’m lucky that mine is plain!

This sweatshirt follows the grey hoodie and black Fuji A.C theme of being a bit on the heavier side with rougher internal fleece, so it’s not worn as liberally as the purple/blue hoodies or the grey crewneck; it’s also a bit hard to layer with due to this fact. However, I am in love with the collar and the sillohuette, as it comes across like a fall/winter polo shirt rather than a true sweatshirt.






Spencer in a reproduction quarter zip. Look at the wide ribbing! His is softer and “looser” (since it’s contemporary), allowing it to be used as a layering piece much easier than mine.




I’m going to finish off by talking briefly about my sweatpants.  The pictures I included in the beginning of this essay wasn’t just for fun, they were for legit style inspiration.  The use of sweatpants today leans toward streetwear or athleisure, but pairing them with classic menswear brings back that more rugged-Americana chic, leaning away from the “cool” vibes and pushing toward a “I don’t give a fuck, but I’m kinda ivy” mindset. It’s certainly onerous not to look too contrived with it, but hey, if you like it why not wear it?

It helps that my sweatpants look a bit preppy! Despite being from Abercrombie & Fitch (bought before I moved into my college dorm), they have no visible branding. The faded black color is plain and doesn’t look like regular athletic wear, while the stripes on the cuff give it a sporty feel.

To me, reconciling the move just means flipping the hoodie look; instead of an athletic top block, it’s now become a bottom block!   If you’ve followed me religiously on Instagram (don’t worry, I won’t mind), you’ll know that I’ve worn sweatpants in the past only a few times, mainly with a sweatshirt, casual blazer or down vest on top, and beat up loafers. I think that’s how it works best. I’m not going to wear it with an OCBD tie and try to pass them off as a trouser alternative to chinos. That would be silly.  I’m not Ronald Reagan.

Now a rugby shirt or polo? That’s fine, because they’re fullbodied like a regular button-up shirt, but infinitely more casual and knit. The lack of buttons on the front, tucked into the waistband of sweats isn’t too silly. This helps everything lean into a more casual aesthetic, marking the way for sweatpants to finish it off.  Plus, rugby shirts were originally athletic wear, so the combination isn’t totally random!

Polishing it off with a corduroy sack-jacket and knit cap completes the look that has that preppy RL, lazy ivy student look that has been the thesis (at least a little bit) of this blog post.  I could add onto this post with more outfits, but I feel like they’re all going to follow the same “uniform” of the one above: sporting fabric jacket (tweed or cord), some form of casual top (polo, rugby, or sweatshirt), the sweatpants, and loafers.


One of the themes of this blog is that regression is your menswear journey is imminent and ever present.  Many times when we get into classic menswear, we tend to jump in headfirst and cast out things that we either did in the past or just don’t feel “right”. Soon, you realize that it’s okay to experiment and be your own thing. That’s why I’ve worn black again and brought back fedoras.  And, in the case of this blog post, I’m wearing sweatshirts, hoodies, and sweatpants again, after years and years of casting them aside.

It always comes down to finding the right source of inspiration and picking the pieces that make sense to you.  I can thank Doug, John, and my diversely dressed friends for providing me the looks and information I needed to make the moves myself.  Now I have hoodies that fit my high rise, straight leg wardrobe and I can even wear them in a way that is authentic to what I like, mixing ivy with milsurp/workwear. It’s also been great to break out my old stuff from high school and college, this time with affection rather than disdain.

So take it from me, don’t sleep on sweatshirts, hoodies, and sweatpants. Vintage ones definitely help, being overall analogous to other vintage sweaters with their cropped length, close fit, and wide ribbing. Or break out your faves from the past and wear them with renewed style knowledge and vigor.

Don’t think you’re being lazy if you wear one! Think of creating an intentional look that goes after those vintage photographs of athletes of the more fashion-forward Japanese-Americana ivy-esque boys. You should always be proud of everything you wear, so you should take the steps necessary to make that happen. That’s what I did, and now I love wearing them.

Always a pleasure,




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  8. vogueorgy · November 15, 2020

    Vintage style is always trending.

    Buy quality T-Shirts, Hoodies, Sweatshirt


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  15. Joe Hermanson · June 24, 2021

    sweatshirts, hoodies, and sweatpants these are forever outfits


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  31. Throwback Vault · January 3

    Such a very nice blog post on “Regressing with Vintage Sweatshirts, Hoodies, & Sweatpants”. This blog is very helpful for readers and fashion lovers. Keep it up good work


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