How to thrift skirts, as a man

How to thrift skirts, as a man

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So, you’re thinking about bringing skirts into your repertoire. BUT–but you’re a man! Or parts of your body are on the ‘male’ side. 

Maybe you’re struggling with the idea of sauntering into the women’s section. Maybe sizing and outfit coordination mystify you. Or maybe you’re looking at a pile of gasoline soaked pants in this very moment, match in hand… cold, ready.

Here’s everything you need to know to navigate this process – preparing for the store, finding the best options, and choosing the skirt ensemble that will make you wonder why you didn’t do this sooner.

But wait, why thrift stores?

Money savings

New skirts can be pricey, especially those marketed towards men. And once you get into skirts, you may find yourself wanting one or two dozen of them. The price point also makes it easier to take risks.

Planet savings

A huge number of garments are out there and still being produced. Fast fashion doesn’t exactly have a good rep for respecting the environment.


You’ll find a treasure trove of skirts that can't be found anywhere else. Don’t worry about trends – we’re in the ‘anything can be trendy’ era. Fashion cycles and revivals now come at a frenetic pace – it’s everything, everywhere, all at once.


They don’t make ‘em like they used to. Older clothes that are still around were often built to last, with higher quality fabrics and hems.

How to prepare

Work up the nerve

If you’ve never dipped into the women’s section of a store, there is that initial ‘oh my’. Most women don’t seem to notice or care – any reaction is often just a smile. And if it helps, many thrifters are looking for costumes across all aisles, so you’ll at least blend in with this crowd.

Inventory & inspiration

Take mental images of your closet’s inventory. Or snap some photos.

Get an idea of the types of skirts you’d consider trying – check our Lookbook for inspiration.

What to wear

It’s all about getting in and out of skirts swiftly. Changerooms can be tedious, when they’re even available. Try to wear slip-on shoes, and clothes with a snug fit. Leggings or tights will let you skip the changeroom altogether, and they pair with skirts like plaid pairs with kilts.

A fitted top that’s a bit shorter, or thin enough to be tucked in, will let most skirts shine. 

You’ll also want to opt for neutral colours that go with everything, like black.

Make a plan

List nearby thrift stores to pop into, and make a trip out of it. 

Bring a friend or partner – ideally, one who wears fem clothing, has a good fashion sense, and is keen on thrifting. It’s more fun with a mate, and they’ll be happy to give you their opinions.

Eat beforehand. Good finds require patience, which can’t compete with a hangry stomach.

In the store

Find the skirts

Make a beeline to the women’s aisles. Or pretend you just “stumbled upon” them while looking at t-shirts. Don’t worry – men’s and women’s sections often aren’t as divided compared to department stores.


Enjoy the selection! There can be a lot, so practice scanning for colours or styles that interest you. Pay special attention to quality fabrics, like wool, cotton, or linen.

Skirt #1?

If this is your first skirt, consider something on the masculine side. For starters, a skirt that could be mistaken for a kilt: knee-length; thick, ruffled, or pleated fabric; a dark colour like black, brown, or green.


Knowing your size equivalent, based on your waist, will save a lot of time:

Women's size to Waist size conversion chart. Sizes, numbers, inches, and cm, with 'Sizes will vary by brand' at bottom.

Caveat: Sizes can have a big range due to things like ‘vanity sizing’. So venture outside your typical size.

Stretchy fabric is forgiving, but comfort is key and you will be disappointed with all the fun skirts that are simply too small.

Women’s shirts are a whole other topic. They pair nicely with skirts, but with our anatomies and cultures, key measurements are often smaller. Make sure the arms are long enough, the shoulders/armpits allow free movement, and that your head can fit through (important).

Reassess your style

If you’ve been wearing skirts for a little while, think out of your box! You’re here anyway – might as well try on some edgy pieces. Something short. Something with a good twirl. Maybe throw in a nice blouse.

Try & decide

Remember that skirts usually sit higher than the waistline – sometimes covering the entire belly. Play around with what feels good, and looks natural. Walk and spin around. Pretend you’re climbing stairs. Dance it out.

Start with a yes pile, and a maybe pile. Think back to your wardrobe… what shapes, colours, or textures could these skirts compliment? How do you feel in them? Could they bring you closer to a look you’re going for? Eventually the yeses become clear.


What if the cashier asks, “Who are these for?” This probably won’t happen but if it does, look them in the eye and say, “They’re for me”. Chances are their head will not explode. If you’re easing into this, or you like to mess with people, tell them you work for a local theater production.

When you get home, have a little fashion show in your room. Mix your new and old garb to see what works. Realize you need more skirts, tights, and tops. Repeat.

For a more nuanced satirical look at this process, read The young man’s guide to wearing and shopping for women’s clothes for the first time

More options

Clothing swaps

This can be as simple as making a pile of garments in someone’s living room, with 5-10 friends who have clothes they’re willing to part with. But the more people, the better. Read How To Host A Clothing Swap Party: Step-By-Step Guide for tips. Don’t be shy to call out in advance that you want to grow your skirt collection (or have some pants to offer). 

Vintage shops

Odds are someone near you is curating some dapper used apparel. Search with keywords like vintage / used / retro / consignment / secondhand / upcycled + clothing / fashion.

Online thrift stores

If you’re not finding much in person, there are plenty of used clothing stores online. Look for those that have a presence in your country or region, to minimize shipping.

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