What to Wear to Flea Markets, Yard Sales and Estate Sales

How to Dress for Treasure Hunting Success

It doesn't matter what you wear when you go secondhand shopping, right? Wrong. Nobody expects a full face of makeup at a 7 a.m. yard sale or an expression of style in an estate sale line, but you do need to be clean, comfortable, functional, respectable, and inoffensive. Here's what to wear to flea markets, yard sales, estate sales, and more:

  • 01 of 04

    Dress Respectable and Inoffensive

    Mother and Daughter Shopping at Yard Sale
    Caiaimage/Paul Bradbury/OJO+/Getty Images

    Dressing to look respectable and dressing to avoid offense are two very different things. The necessity of the former is mostly fair. Mostly. The latter usually isn't.

    However, failing to do either can cost you cash when it's time to haggle — and can even reduce your access to the best merchandise.

    It's for Sale, but Not to You

    How does that happen? And why? Reduced access to the merchandise is more likely with amateur sellers. You'll find them at yard sales, private estate sales (meaning not organized by an estate sale pro), and charity-based thrift stores staffed by volunteers.

    If you don't look respectable, those sellers may worry that you'll steal or spoil the merchandise. If something about you offends, an emotionally attached seller might even feel like you don't deserve her stuff.

    Consider the following situations:

    • You see an antique wing chair covered in gorgeous silk damask. But, just as you're about to sit, the seller rushes over and tells you it's already sold.
    • You're about to try on a pair of vintage Ferragamo pumps you've spotted at the thrift store. Before you can slip them on, the clerk grabs them and tells you they were donated by mistake.
    • You've waited in an estate sale line for an hour, and you're number 10. Just as you're about to step over the threshold, the seller sticks his arm out and tells you they're limiting entry to only nine people at a time.

    Every single one of those situations could be legitimate. But, they could also be examples of sellers blocking you from the merchandise.

    It can also happen without you ever having a clue.

    Perhaps you're at a yard sale and looking for something specific. You don't see it on display, so you ask the seller.

    If you don't look like someone she'd have in her home, she's not going to invite you inside — even if she has what you want. And, she's not going to leave you outside with the rest of her sale stuff while she goes in to look. 

    The Haggling Handicap

    When it's time to haggle, amateur sellers aren't the only ones who may penalize you because they don't like your look. Pros have just as many prejudices. 

    It makes no sense since they want to sell that stuff. But, some sellers will punish you by not giving you the price you want — even when they'd readily give it to someone more like themselves.

    Dressing to Look Respectable 

    Dressing to look respectable is easy. You don't have to dress like you're going to work. Just make sure your clothing, body, and hair are clean and neat. Wash off last night's smeared eyeliner and change shirts if the baby spits up on you.

    Also, avoid showing more skin than is appropriate for daytime in public according to the general public. In other words, don't wear your clubbing clothes. 

    Dressing Down to Haggle

    Good haggling advice frequently includes tips on dressing down as a haggling strategy. The idea is to avoid the appearance of wealth. But, avoiding the appearance of wealth isn't the same as looking like a bum, so people give you low prices as a charity.

    Don't Be Offended by Looking Inoffensive

    Don't be. It's for you, but it's not about you. It's about avoiding any prejudices (conscious or subconscious) the seller has.

    People want to do business with people they like. And, even though it's unfair, lots of people dislike people who don't agree with them, including some sellers.

    Since secondhand shopping means doing business with lots of strangers, your goal is to be as inoffensive as possible to as many of them as possible.

    So how do you do it?

    Avoid wearing things that reveal any opinions and positions that other people could find controversial or provocative. Skip clothing and accessories that advertise your positions on politics and religion. Don't wear things that overtly reference sex, even jokes. 

    Summarizing What Not to Wear

    Bearing all these things in mind, here are some things you should avoid wearing while you shop:

    • T-shirts with political, religious, or sexual slogans and images
    • Dirty, stained, stretched out, or torn clothing
    • Pajamas (not even just the pants) and house slippers
    • Stuff that shows too much cleavage or any exposed rear end
    • Clothing so sheer or tight that airport security lets you skip the line
  • 02 of 04

    Comfort Is Key

    Young Woman Shopping for Books at Flea Market
    Mika/Corbis/Getty Images

    Treasure hunting is a very physical activity. You're going to be walking, digging, bending over, lifting, hauling, and nearly turning yourself upside down.

    Your goal is to make sure your clothes are up for all of that activity — and that you'll be comfortable while you do it.

    You also have to be able to move quickly. 

    When you and that dreaded dealer both spot a box of Bakelite kitchen utensils selling for 25 cents a pop, there's going to be a race. If you're hobbled because your heels are giving you blisters, it's a race you won't win.

    Avoid Irritating, High-Maintenance Clothes

    Truly comfortable treasure hunting clothes are comfortable all the time, not just when you stand still — and you don't have to adjust them constantly. 

    If you have to pull, tuck, tug, and twist what you're wearing to keep it in place, next time you need to wear something else.

    That loose flowing blouse with the big scoop neck might feel fine when you're meeting a few friends for lunch. But, if it flaps open when you bend over to dig through a box, you'll be more worried about flashing than shopping.

    The same goes for pants that slide down. Get a belt or opt for something else. You can't grab your pants to prevent an incident when you've got both hands full of your fabulous flea market or yard sale finds.

  • 03 of 04

    Function Is Always Important

    Woman Buying a Dress at a Flea Market

    Hans Alm/Folio/Getty Images

    If it goes on your body, it's functional, right?

    Clothing that's functional as clothing is different than wearing something practical while you shop at flea markets, yard sales, and other secondhand sources.

    Trying on Clothes

    Perhaps you're shopping for clothes, whether vintage, indie, and original or newish and gently used.

    Some thrift stores have dressing rooms, but not all. And you'll probably never find a fitting room at a flea market, estate sale, or yard sale. That means you have two choices:

    1. You can buy it anyway and hope it fits.
    2. You can try it on in public.

    If you go with option two, you need clothing that's functional for that purpose.

    Look at the woman in the photo. She's wearing a close-fitting sleeveless top and a thin skirt that's neither overly full nor super tight.

    She can slip that sweater she's holding on over her top. She can try on most dresses over her existing outfit as well. She can also put on pants and pencil skirts under her skirt.

    If you can't imagine wearing a skirt to a flea market or yard sale, opt for a close-fitting tank and leggings instead. Then, wear a longer, looser open shirt or jacket over it for more coverage when you're not trying things on. Light layers always work.

    Coping With Changing Weather

    Light layers are also functional when the weather is prone to change. If it's chilly early in the morning and scorching once the sun is high, wearing two or more light layers lets you add and subtract as needed.

    Staying Hands-Free While Carrying All That Stuff

    It's not all about turning a public place into a fitting room. You also need a practical way to carry your treasure hunting toolkit, which includes your measuring tape, wish list, flashlight, etc. 

    The exact things and the amounts you carry depend on where you shop and what you're hoping to find. If your load it light, make sure your pants have pockets, and you can probably slip all of your stuff inside.

    If you carry quite a bit in your kit, consider some bag that lets you keep your hands free to shop.

    A cross-body bag that hits somewhere on your hip (below tabletop height) works well. A belt bag (today's updated, more stylish version of the dreaded fanny pack) is also a good option. And, if you don't want to deal with a bag at all, consider a fisherman's vest with lots and lots of pockets for stashing your stuff.

  • 04 of 04

    So I Can't Just Be Myself?

    Stylish Man Shopping for Jeans at a Thrift Store
    Ryan McVay/Photodisc/Getty Images

    Of course, you can be yourself. You don't have to let your appearance reveal every single thing about you to total strangers.

    This is for your benefit. It's to keep the sellers' prejudices from working against you when you're trying to snag fantastic stuff and get it for a killer price.

    This is about being smart, not fake.

    It's no different than concealing your excitement for haggling purposes when you spot the find of your dreams. You're hiding something about yourself, specifically your desire for that particular item. Does that make you a fake? No, it makes you a smart shopper.

    Does any of this mean you can't dress to suit your personality? Assuming you can even think of that during the wee hours when successful treasure hunters head out, absolutely not.

    Take a look at the sharp gentleman browsing thrift store jeans in the photo. 

    He's not revealing anything about his politics, religion, etc., but he is showing some of his personality. You can tell puts thought into his appearance, he likes clothes, and even that he leans a little bit retro.

    He's extremely stylish, but his choices follow all of the rules (note the strap to his cross-body bag for function).

    If this shopper heads to a private estate sale next, how will the seller feel when he starts browsing her deceased dad's vintage wardrobe?

    If she's sane, she'll give him a great deal on those sentimental items because she can tell he'll give them a good home.