Part 1 of a Thriftista series: Thrift shopping & resale

Updated April 2025.

Years ago, I found thrift shops to be rather grotesque—just the thought of someone else’s clothes [or shudder to think, their shoes!] made me itchy. Still, I’ve friends who love them, so I paid attention. Forget some of the vintage stuff—that’s not for me. But look, here’s a Lululemon shirt in great condition, for $4! And over there, a Chanel bag that needed a little stitching for $7!

Move over, Michigan Ave.!

Plus, shopping secondhand means reducing landfill waste, lowering your carbon footprint, and opting out of fast fashion’s exploitative practices

As part of this series, I’m going to discuss:

• Thrift shopping dos and don’ts, local shops [that’s this one]
• Great Chicago and suburban shops
• Resale pointers

Look for labels

Generally, big brand and designer names hold up better and are better taken care of than Old Navy and H&M wares. It may be a deal at $2, but the cheapies don’t last too long in the wash.

Inspect before you buy

Look out for stains, loose seams, or missing buttons. If you’re handy with a needle or steamer, small flaws can be easy fixes. If not, figure a tailor’s cost into the item’s price. Most stores won’t make deals for damaged items, and not everyone does returns.

Touch is your superpower

Get in the habit of feeling for natural fibers—cotton, linen, wool, silk. They wear better and feel luxe.

Go often and stay flexible

Inventory changes daily. The magic happens when you’re not looking for something specific.

Always try things on

Sizing varies wildly—especially vintage. Don’t trust tags. Trust your fit.

Set a budget + bring cash

Helps curb impulse buys and some smaller stores offer cash discounts.

Plan to look for a while

If you find a great shop, plan to be there for a couple hours. And wear something you can easily toss something on over such as a tank top—if they don’t have a dressing room or the line is long, you’ll be done faster.

A smartphone is great for thrift stores [and flea markets]

If you’re unsure of a brand’s pedigree, you can look it up online (the Google app/Google Lens is your best friend!). I’ve found some obscure yet pricey Italian designer bags at SA in great condition. It takes a critical eye [or you simply fall in love with it anyway] but these items can be found for less and no one is the wiser [unless they read this post].

And probably most important, realize that all shops are not created equal

Some specialize in vintage [read: of a particular era], some only keep current seasons [and hence often a higher price tag], some are a mish-mash of everything. If one shop doesn’t appeal, don’t write them all off. I’ve found amazing deals at low-rent shops, and junk at some high-end shops. The key is to find what you like, at prices you can justify. Some shops also offer more services [esp. the boutique-y ones], like the shop manager who keeps your style and sizes in mind for future shops. This is just called great customer service!

If you don’t want clothing, many have shoes [including those unworn but discarded by fashionistas—I found Franco Sarto boots for $10 at Crossroads Trading Co. with the original tags still on and no wear], kitchen items, bedding and various sundries, toys, books, camera equipment… yeah, you name it!

And also, pay attention to your stores’ merchandise. Neighborhood does matter! The SA off of Clybourn is their hub and generally has the best of the lot, whereas I’ve not had as much luck in their suburban counterparts, unless it’s in a “good” suburb. SA also takes Target’s donations, so if it’s out-of-season, it may end up at one of their shops.

What tips do you have?

UPDATE: Goodwill shared this article when I first published it!