One of the best compliments I can get when I’m wearing a fun outfit is, “Wait… that’s thrifted?” Not because secondhand should be embarrassing (it shouldn’t!), but because it means my outfit is doing what it’s supposed to do: looking intentional, and current — and not like a costume.
When I thrift clothing, I am almost always looking for pieces that don’t look vintage, necessarily, but look like they could have come from Net-a-Porter or Moda Operandi. In other words: even if I’m spending $5, I want the piece I purchased to look like it was expensive.
I find that I often buy first, think-about-styling later — grabbing pieces that resonate with me in the moment (and promising myself I’ll figure it out once I actually put the thing on).
But I realize I may be alone on an island in that mentality. Most of us probably want to know how something can be worn or prove useful before we actually fork over our hard-earned money for it.
So with that in mind, I’ve developed a somewhat sprawling guide full of outfit ideas for pieces you will likely come across at the thrift store (or at an antique mall, estate sale, etc.)
Below are a ton of outfit ideas I turn to when I’m trying to make thrifted pieces read as “elevated,” “designer,” or at the very least: not thrift-store-y.
The Item: A Funky Blazer
First off, let me say that thrift stores are full of patterned/strong-shouldered/well-structured jackets and blazers, because we simply do not wear power suits anymore! I always check the ladies suits at the thrift, and have found so many designer pieces here, from Ungaro to Dior. I never wear suit sets together, choosing instead to style the blazer on its own and wear the skirt with a thrifted tee, or hiked up as a tube top.
Blazers actually have endless styling possibilities, making them really fun to style.
Easy outfit formula:
thrifted patterned blazer + button-up blouse + well-fitting jeans + sneakers (think Adidas Sambas or Gazelles, not New Balance or workout sneakers)
How to fake a tailoring job:
cinch the waist with a belt or scarf
push the sleeves to your elbows and use a hair elastic to keep them in place
Easy outfit formula:
blazer sans shirt (but with a big brooch, like a flower) + straight-leg jeans + masculine boots (think cowboy or workwear boots, to juxtapose the fancy jacket)
Some options:
Ungaro zebra blazer, 1980s Dior blazer, wool Adolfo blazer
The Item: A Vintage Tee
Easy outfit formula:
thrifted novelty tee (with the sleeves cuffed, to make it appear more fitted, and tucked in) + leather pencil skirt + pumps + structured bag
How to fake a tailoring job:
tuck it in
cuff the sleeves
Other t-shirt scarf styling ideas:
loosely, with similarly loose (but patterned or at least silk) trousers, tucked in to trousers and worn with a suit (along with heels or sneakers)
Some options:
1970s thrashed tiger tee, 1980s dirt track racing tee, vintage Playboy ringer tee
TIP: If you want a thrifted tee to smell new, use a high-quality deodorizing detergent. This one is free and clear of fragrances and toxins and was named among the best by Wirecutter. I recently started using it, and it’s great.
The Item: A Long-Sleeved Button-Up-Top
Easy outfit formula:
thrifted button-up (worn un-tucked) + wide- or straight-leg trousers or denim blazer + heels or boots + a scarf tied around the waist
How to fake a tailoring job:
cinch the waist with a belt or scarf
push the sleeves to your elbows and use a hair elastic to keep them in place
play with the buttons (try buttoning only the bottom half of them, or even just the one in the middle, and wearing it either sans shirt or with a plain fitted tee beneath)
Easy outfit formula:
thrifted button-up (worn un-tucked) + wide-leg trousers + a bustier or corset or harness on top (something cropped that would be considered sexy without the shirt underneath)
Some options:
pink Ralph Lauren button-up, Italian rayon button-up (under $35!), Tommy Hilfiger corduroy button-up
The Item: A Dramatic Bolero
Not to be confused with the aforementioned blazer, a bolero is a little bit different, because it’s cropped (and often comes with an evening dress if you care to check the “fancy dresses” section of the thrift store). Anything cropped can be hard to style, IMO.
Easy outfit formula:
cropped bolero sans shirt + high-waisted skirt + big earrings
Easy outfit formula:
bolero + simple tank or camisole + cuffed jeans + sandals
Some options:
Ungaro silk striped bolero, 1980s velvet and beaded bolero, multi-colored spiral bolero (under $30!)
If you’re a paid subscriber, the rest of this post gets very specific:
Styling ideas for: vintage scarves, brooches, and Hawaiian shirts
My go-to sites for styling inspiration
The fabrics I always look for at the thrift store
When to get something tailored
