How to Wear Weird Wacky Vintage

so it doesn't feel like you're going to a costume party

Jul 11, 2025

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Though I consider myself a lifelong lover of all things old, kooky, strange, and unique, I didn’t actually start collecting and investing in true “collector” vintage pieces for my wardrobe until about seven-ish years ago. While there was always an occasional one-off piece I would fall truly madly-deeply-can’t-live-without-it in love, I found that every time I tried to wear something bold, something recognizable, something that predominantly defined an era, I immediately felt like I was wearing a costume. The debate of what shoe to wear, whether or not bold lipstick worked, the back and forth of how many accessories were too many accessories exhausted my self confidence enough to scare me away from wasting my precious dollars on things that would simply be shoved to the back of my closet.

Discovering how to make vintage clothes work for you, your personal style, your lifestyle and your modern wardrobe is an ever evolving journey that requires only one step: starting.

Committing to shopping mostly secondhand and vintage has helped tenfold in getting over my fear of looking like I’m always dressed for a Halloween party (though, the older I get I’m not sure I have a real problem with that...) In the last seven years I’ve tried on hundreds upon hundreds of different eras, fabrics, and silhouettes of clothing that have helped me determine what fits into the aesthetics of my heart (and my closet.) I now know I’m not a gal who is going to rock a 1950’s fit and flare dress but that I am someone who will collect every velvet opera coat that comes my way.

By far the most common feedback and requests I receive are from peeps wondering how I would style something I’ve included in a round-up or sharing their intimidation in pulling the trigger on that expensive vintage designer statement piece. Hopefully this dispatch will encourage you to start incorporating more one-of-a-kind pieces into your wardrobe — which I stand by as being the absolute best thing you can do to develop style that is deeply personal to you!!!

Before I dive in, I want to restate for the millionth bajillionth time that I personally find fashion rules to be dumb and arbitrary and believe they exist only to make you buy things or hate yourself (“cool girls buy this blah blah blah”). Everything I’m about to say are tips and tricks I have found work for me and might work for you if we have similar brains that think the same silly thoughts. It’s really not that serious, and if you feel beautiful and wonderful and fabulous in wearing the boldest of outfits with the boldest of makeup with the most voluminous hair — hell to the motherfuckin’ yeah!

Where to Find Inspiration

If you don’t know where to begin in figuring out what kind of vintage makes your heart pitter pat, consider using these tips before anxiously adding to cart. We’ve reached a point in the timeline where just about everything is a reference to a reference to a reference — use this to your advantage.

Browse runway collections
This is a wonderful starting point to determine what you’re drawn to repetitively — maybe it’s big, bold statement jewelry from an 80s collection, a funky pant silhouette from an early 90s collection, or an iconic couture collection filled with velvet and brocade. I personally always look to modern designers like Alessandro Michele, who is a master at mixing vintage inspired pieces with modern silhouettes in a way that feels rebellious yet harmonious. Screenshot these finds and save them to a folder you can reference and find similarities that you can use as search terms when browsing eBay or Etsy.
Find a vintage fashion muse
If you’re a Seasoned Trash Head, you know I’m not one for directly referencing people’s (influencers) exact outfits (it dulls the senses and more often than not, feeds the insatiable overconsumption gremlin). But!! when it comes to discovering your vintage taste, I do believe this is a good starting point in seeing how other humans combine new with old, accessorize, and style themselves in a way that feels congruent. Everyone has a slightly different take which is really the magic of it all. 🚨Hot tip alert🚨 a good way to find said fashion muse is to go to your favorite vintage store’s IG (don’t have a favorite vintage store? start here and search their vendor list) and lurk their tagged photos — so many folks tag where pieces of their outfits are from. I’ve found many a cool person this way!
Watch TV period shows and old films
People often ask why I am the way I am (read: an old person in a young person’s body) and the answer is that I was raised by my grandmother and our favorite weekend activity was watching Fred, Ginger (watch this one), Bogie, Bacall (watch this one), Lucy, and Desi (if you don’t know, now you know.) Being exposed to film and TV from other eras has undoubtedly shaped my style and there’s a reason I find myself consistently drawn to certain silhouettes and outfit formulas that reference certain moments in time. I’ve rewatched Peaky Blinders more times than I can count, having screenshotted just about every interior shot filled with lush velvets, fringe lamps, Chinese Art Deco furniture and delicately embroidered textiles. I know it’s something that is undoubtedly *Glenn*.

Where to Shop

This is one of the few times I will recommend starting with Etsy over eBay, despite their search function being absolute garbage with a forever shifting algorithm. Many well respected, highly coveted vintage sellers still sell on the platform and generally, it’s an easier place to find pristine, curated “statement” vintage. Always make sure to put “vintage” in the search bar before your keywords and be aware of listings that look scammy — I only shop from Etsy stores with reviews from real people. Many of the finds linked below are from some of my favorite Etsy shops! Save them to your favorites! eBay is still a fantastic option, though it is more likely you will have to commit to bidding or digging through a lot of pages (my favorite 😈)
Attend a vintage show! Find one in your local community (I go to Twin Cities True Vintage), or plan a trip around some of the iconic traveling shows like A Current Affair. Not only is the people watching incredibly inspiring, but most vintage sellers and dealers are small business owners that want to connect with their client. Ask questions! Tell them what you’re on the hunt for! Ask for styling advice! Introduce yourself! I’m a super-colossal-shy-girl and just finding my footing with this, but I promise you, it makes all the difference. I’ve had sellers pull out boxes just for me to dig around in, tell me stories of how they came to find certain things, and even been offered special deals all from striking up a conversation. I’ve learned so much about certain textiles, eras of stitching, and literal world history through connecting with dealers at shows.
Use the Gem app — it will do so much of the work for you! Gem combs multiple secondhand, vintage, and resale shops, including the occasional one-off online vintage store I never would have found otherwise. You can save searches if you’re on the hunt for something specific and it’s incredibly helpful for finding the best price on certain coveted vintage things like silk pajamas, fur coats, etc etc. I spend a lot of time on Gem just searching by era (“1930s pajamas”, “1960s mini dress”)

What to look for

Fabric composition is extra important, especially if you’re like me and have a boatload of sensory issues. Find the cutest Pucci blouse for your Palm Springs trip? Better make sure it’s not thick polyester or heavy nylon because you *will* wilt in that hot summer desert sun…
Flaws, stains, fragile textiles, and visible mending. Rarely is vintage pristine, even if it’s been impeccably stored, barely worn, or handcrafted designer couture. The price you are paying is often a reflection of its rarity and condition, but also the work the seller has done in making the garment buyer ready. Some antique clothing can disintegrate or begin breaking down, which is important to consider before investing thousands on something that should probably live in a museum (like lace, fine beading, netting, silk, etc)
Know your measurements. Before you invest in that iconic vintage 1972 Oscar de la Renta you’ve fallen in love with, determine if it will actually fit your 2025 body. Measure parts of your body you don’t often consider (wrist and neck circumference, arm pit to top of shoulder, etc) and message sellers for specifics. Many vintage pieces were custom made and have unique measurements.

Other things to consider:

Imagine what the item “could be” — an easy way to make something feel more akin to your modern wardrobe while honoring its vintage charm is tailoring. This could mean hemming a maxi dress to be a midi length, taking a knee length skirt suit and hemming it into a mini, taking the sleeves off something, etc etc
Avoid wearing head to toe vintage and a vintage hairstyle and a full face of glam if you don’t want to feel like you’re about to go trick-or-treating or attending a Dita Von Teese lookalike contest. Play around with finding a balance that works for you! I tend to lean modern, easy going hair and play around with either a bold eye or a bold lip, but rarely opt for both.
Pair the crazy wacky vintage statement thing with something funky but modern. It will feel like you’re paying homage without looking like you’ve jumped out of a history book. This is where I feel building a designer core wardrobe (shoes, jackets, bags, sunglasses) can be a worthy investment — a chunky Gucci platform, groovy Dries Van Noten heel, or sleek block-shaped Khaite flat to pair with your 60s couture feels elevated and artsy fartsy (in a good way) and less like you bought everything available at the local antique mall.
If you’re intimidated, start with something simple as a gateway piece. A vintage tee with your every day favorite jeans but add a funky vintage statement necklace. A vintage dress with a simple pattern, paired with your favorite sandals and every day purse. You don’t have to immediately step out in the gold lurex ball gown with puff sleeves even if that’s your dream! Baby steps.

Now for the fun part, all my finds. I focused on more summery pieces, but I just might do this again as we approach cooler temperatures (especially if you tell me this was helpful in the comments, hint hint hint)

Let’s get into it.

If you make a purchase through a link, I may earn a small commission, which I appreciate as it helps fund this space ✨ This round-up contains links to new items, a rarity in this space. I wanted to illustrate how vintage items pair well with things you might already be considering for your modern wardrobe. I shop for clients in my life outside of this corner of the internet and most of the items linked are from websites, brands and designers I regularly touch, feel, and interact with.

Beachy, summery, functional yet funky — I styled this to the ultimate level of wacky weirdness, but you can easily pair this vintage knit dress down to feel more casual and modern just by playing with accessories.

maryam keyhani tan souffle hat (€420,00, ships from Berlin) - i need all of her hats, STAT
kenneth jay lane hammered gold coin necklace ($249, purchase on eBay)
plaid knit dress (available in fem small and large, $148)
dorateymur brown sunglasses (very good condition, $115)
vintage bakelite bangle set (set of 4, $34.99, purchase on eBay)
woven leather patchwork purse ($110)
loeffler randall boat shoes ($325)

Perfect for a desert vacation or a summer day running errands. A psychedelic print can feel very costumey but paired with more casual items (a larger bag and chunky clog) brings it to this current decade.

sterling silver round drop earrings ($88.18, purchase on eBay)
1960s psychedelic romper (see measurements, $78)
black loewe round sunglasses (very good condition, $204)
khaite raffia hobo purse (good condition, $1025)
alaïa laser cut leather clogs (fem 6, very good condition, $195.50) - i forever love a clog and it’s one of the few laser cut things from alaïa i think is super cute

Most pieces from the 90s might not feel all that costume-y, but I still think bold prints and colors generally intimidate. Brown is an underutilized neutral that can make something feel dressy without feeling stuffy and boring and formal.

by malene birger satin cape (fits fem xs-l, $280)
moschino jeans watercolor dress (vintage fem 8, $270, purchase on eBay)
justine menard blown glass earrings (€175.00, ships from spain) - i dream of these earrings — all of her work is stunning and absolutely collectible works of art
bottega veneta metallic clutch (very good condition, $940)
dries van noten brown patent leather heels (fem 39.5, $477 on sale)

I’ve included a few dresses in a similar silhouette before and think it is a particularly good one for playing around with statement vintage. It would also work with a flat sandal, chunky wedge, or strappy stiletto, which means you can rewear it for multiple events.

anne klein lucite drop earrings ($369)
1970s miss elliette floral maxi dress (see measurements, $135)
cult gaia shell camilla clutch ($298, on pre-order) - okay this bag is insane!!!
sterling silver topaz cocktail ring (size 7-7.5, $55.99, purchase on eBay)
gianvito rossi gold stone detail sandal heels (fem 11, very good condition, $745)

I personally collect vintage outerwear because it is easy to pair with most modern evening wear (and even looks cool over a vintage tee and jeans)

christian dior faux pearl earrings (good condition, $292)
1950s olive green silk opera coat (one size fits most, $155)
la doublej floral feather trim dress (fem m, excellent condition, $374.50)
timmy woods black roman column purse ($139, purchase on eBay)
alexander mcqueen black satin ankle strap heels (fem 6, pristine condition, $425)

Can you tell I’m dreaming of the desert? This feels like you could be plucked right out of the late 60s in Palm Springs, but has enough modern elements and shapes (weird sunglasses, a more modern feeling stripe) that pull it out of the costume category.

kenneth jay lane rhinestone starfish earrings ($80, purchase on eBay)
1960s psychedelic crop top (vintage fem m, see measurements, $99, purchase on eBay) (similar here and here)
simon miller striped poplin pants (fem 0-14, $245) — comes in multiple colors (all of which are fun)
loewe round yellow sunglasses (very good condition, $228)
koret woven wicker rattan purse ($65, purchase on eBay)
loeffler randall gold slingback shoes ($295)

This is simple but I promise you will be the best dressed at the event. I’d wear my hair up, but in something loose that feels a little lived in and stick with very simple make up, perhaps a matte rosy lip.

pearl cluster earrings ($45)
issey miyake striped tent dress (fem l, $568)
simone rocha pearl clutch (pristine condition, $625.50)
balenciaga pink knife mules (fem 6, very good condition, $410)

It’s giving “the coldest winter I ever spent was a summer in San Francisco” vibes, but is also an example of how having a more casual style can still mean occasionally dabbling in a statement piece.

red suede fringe jacket (vintage fem l, $199.99, purchase on eBay) - i consider a vintage suede fringe jacket to be a “must have” wardrobe staple for everyone and this one is a fabulous color
1970s single stitch soft tee (vintage s, $65, purchase on eBay)
versace jeans couture cherry jeans (vintage fem 29, $398)
chloe blue leather purse (fair condition, $410)
lizzie fortunato pearl charm necklace (very good condition, $295)
jeffrey campbell jelly sandals (various color ways and sizes, $65) - i’m not usually one for a dupe, but i can’t help but think these are weird in the best way and there’s no way paying $500+ makes any sense

This is my ode to Carrie but also something I would totally wear to a night-out-on-the-town (read: a happy hour martini, steak dinner, and being in bed by 9). This look leans on “the weirder and more unique the better” philosophy, which comes from ample time playing dress up in your closet.

bode black crochet cap ($390) - we all know how i feel about bode, but i cannot lie, this is really fun and decently hard to find and even though i should just learn to knit, i will continue to be tempted by this
1970s vintage miss dior by oscar de la renta striped blouse (see measurements, $225, purchase on eBay)
junya watanabe x comme des garcon sequin mini shorts (fem xs, excellent condition, $90) - calling all petite friends!
vintage playgirl magazine clutch ($150, purchase on eBay) - this price is GOOD, magazine clutches are becoming (and not all of them have cool graphics like this)
bottega veneta slingback heels (fem 8.5, very good condition, $261.25) - an underrated color combo, if you ask me

A vintage statement maxi that works for everything from a wedding guest look to a vacation dinner look. (This is where you want to make sure you’re checking the fabric composition so you’re not miserable!)

louis vuitton leather studded earrings (very good condition, $395.50)
1970s malcom starr caftan dress (vintage m, $459, purchase on eBay)(similar and very cool alt options here, here, and here)
vintage brutalist bronze cuff bracelet ($54.44, purchase on eBay)
timmy woods wood carved handle purse ($199.97, purchase on eBay) - ngl, sad i didn’t snatch up all the timmy woods before the substack girlies discovered him so plz buy this because they are becoming more rare, this price is decent, and this bag is killer!!!
a. emery black leather sandals (various sizes, $200) - there’s a reason everyone is obsessed with these and i feel they work well even for very dressy occasions

Another option for someone intimidated on where to start when it comes to vintage — this outfit feels modern and a little flashy but can easily feel more casual with a shoe or bag switched out. The jacket will come with compliments, I promise you.

alexis bittar gemstone dangle earrings (excellent condition, $180)
vintage beaded jacket (vintage fem m, $350)
madewell longline straight jeans (various sizes, $148) - i worked at madewell for almost five years and while i think they’ve generally lost the plot (lol) i really like this fit and wash, especially in petite sizing as a five foot one gal
givenchy green satin heels (fem 9, pristine condition, $260 on sale)
vintage metal butterfly purse ($79, purchase on eBay)

I think 80s silhouettes can feel costume-y because of the exaggerated shoulders and pairing with thoughtful modern pieces can make the look feel more purposefully sculptural/artful.

wayne clark black chiffon dress (vintage fem 6, $149.49, purchase on eBay) (similar and fun option here)
silver tone cabochon adjustable belt ($76, purchase on eBay)
chaan luu sterling silver lily drop earrings ($325) - these are pricy but i like the length of the drop, which feels very whimsical (more affordable vintage options here and here)
sterling silver modernist cuff bracelet ($299.99, purchase on eBay)
dries van noten snake skin heels (various sizes, $537 on sale) - i’ve been coveting these forever and waited too long and my size is sold out so let me live vicariously through you!
mansur gavriel green baci clutch ($995) - yes, the price is ridiculous but it’s giving golf turf and i’m very into it and extra bonus points for the item description specifically mentioning that it “fits all sizes of phones”

The hat is *the* moment, but doesn’t feel too Dr.Suess-y when paired with every day casual accessories like a big worn-in bag and your favorite low profile sneakers.

1960s blue straw summer hat ($125, purchase on eBay)
1980s blue silk wave dress (vintage fem l, $198)
gold tone articulated fish necklace ($125, purchase on eBay) - the chain being fish scales is !!!
green and yellow glass bead necklace ($29.99, purchase on eBay) - collecting eclectic vintage jewelry is great for playing around with old and new/pairs well with fine jewelry
bucherer round face watch (good condition, $500)
vintage louis vuitton vernis bag (fair condition, $260) - i am a firm believer in a beat up beat up beat up bag for errand running, travel, etc — i love something that feels lived in
novesta cap toe sneakers (various sizes, $100) - i love a gummy sneaker that feels simple, classic, slim profile, not too heavy and think they can be a key player in the vintage yet modern balance (i also like the ralph lauren version and jack purcells)

This one may feel a little advanced (lol) — I personally like to feel really eclectic and play around with textures and colors and mixing “fancy” things (like the metallic bag) with really casual things (like the sandal)

loewe cat eye double sunglasses (pristine condition, $422.75)
vintage hand painted caftan (see measurements, $75, purchase on eBay) (other fun option here) — hand painted!!!
lucite bangle set ($48, purchase on eBay)
paco rabanne metallic coin purse (excellent condition, $600)
veronica beard carmina paracord sandals (various colors and sizes, $275) - paracord is very trendy right now but i’m picky about sandals and think these feel interesting without being too much

Well, there ya have it! As always, let me know if something isn’t linked correctly since that’s the part that makes my brain explode a little.

Tell me your thoughts in the comments! Hopefully this was helpful and not the ramblings of a lunatic!!!

Please ignore all my typos this took me forever and I’ve read it too many times lol

Until next time,
xo,
G