The Art of Thrifting feat. Westley Dimagiba

November 13th, 2012

I’ve been thrift shopping since 2006 and it has become one of my favorite hobbies. I love the hunt, and it can be very rewarding. In fact, I’ve found most of my wardrobe at thrift, goodwill, and secondhand shops – all at ridiculously low prices.

The secret is patience and frequency. Not one day goes by that I don’t check the vintage store in my neighborhood. I’ve also become acquainted with the owners and employees there, who often call me when new duds arrive in my size. Sometimes, too, I’ll let them know about specific items I’m looking for, with the hope that they’ll think of me during their next buying trip.

The following are some of my favorite vintage finds, along with tips from the Articles of Style team on the art of thrifting.

1. Vintage Layers

Vintage store items are one in a million. So if you want it, buy it now! Chances are, if you leave it behind it will get scooped and you won’t come across the same piece again.

This Ralph Lauren lumberjack coat is one of my go-tos for Fall/Winter. To be honest, the sleeves are a touch short, but the body fits just right and I had been looking for a jacket like this for a while. When you’re getting a $300 jacket for $30, you might have to compromise a little.

Here are some things that can help you determine the quality of a vintage item:

1. Brand name. I hate to sound like a “label whore” but knowing who manufactured an item gives you an idea of the expected quality. Of course, this doesn’t necessarily mean that non-brand items are low quality. Personally, I have some amazing no-name pieces, like this corduroy waistcoat.

2. Fabric content. Look for organic fibers (like wool or cotton) and avoid blends with a large amount of synthetic fibers (like polyester and rayon).

3. Feel it. The “hand” of a cloth can tell you a lot. Generally, the softer and sturdier the fabric, the better it will wear.

4. Try it on. A well-cut garment can be slim and fitted without being overly restricting.

5. Check the hardware. If the item has zippers or snaps, give them a test run. Cheap clothes have cheap hardware that “sticks” are breaks.

Vintage head-to-toe is not easy, but it can be done (see our post on All Vintage Everything). Here everything is secondhand, with the exception of the pants.

These basket-weave lace-ups are not the highest quality, but I get compliments every time I wear them. Not bad for $30.

  • Spectaculars eyeglasses by Fabulous Fanny’s ·
  • Red plaid jacket Vintage by Polo Ralph Lauren ·
  • Beige corduroy vest Vintage ·
  • Blue denim shirt Vintage ·
  • Navy blue corduroy pants by JCrew ·
  • Brown basket weaved shoes Vintage

2. Bombs Away

Not every trip will be a successful one, but sometimes you hit the jackpot.

The moment I tried on this leather bomber, I was in love and didn’t want to take it off. If that feeling doesn’t hit you, skip it because something better will come along. Don’t settle in a vintage shop, they typically have a very high turnover.

As a friend of mine always says, “If you have to question it, then you don’t really want it.”

This is a great example of the one-of-a-kind pieces you can only find at vintage shops.

A shearling-lined leather motorcycle jacket with oversized lapels and a belted waist – it doesn’t get much more unique than that.

A statement vintage jacket is a great way to ad some personality and edge to a more typical prep-inspired look.

Don’t forget to keep an eye out for accessories too. I found these awesome leather gloves for like $10 or something like that.

  • Brown leather bomber jacket Vintage by Schott ·
  • Green/Navy rep tie by Rugby ·
  • Navy striped sweater by GANT Rugger ·
  • Burgundy corduroys by Levi’s ·
  • Brown unlined leather driving gloves by Cole Haan ·
  • Suede chukka boots by Scarpe di Bianco
  • · White club collar oxford Vintage

White USA Oxford Shirt

3. Grandpa Cardigan

Making a list before thrifting is a great way to stay organized and avoid aimlessly wandering the unorganized racks of clothing.

I keep an updated memo of “things to add to my wardrobe” on my phone. It took a few trips, but I was able to snag this chunky shawl cardigan and cross it off my list.

Don’t forget to properly inspect the items before purchasing, too. Look for stains, moth holes, loose threads, worn out spots, etc.

Let’s be honest, practically everything in a vintage store smells. After buying second-hand clothing, your first stop should be the dry cleaners, followed by the tailor (if necessary).

The beauty of vintage clothing is that “they don’t make them like they used to”.

Clothing used to be made to last. This sweater, for example, is a beast. Made from a heavy, sturdy wool that won’t stretch out and lose its shape over time.

I like to mix vintage pieces with more modern looking ones, like these awesome kilted boots designed by Ronnie Fieg (as featured here) in collaboration with Sebago.

  • Neutral wool cardigan Vintage ·
  • Red/navy flannel Vintage by Polo Ralph Lauren ·
  • White long sleeve henley Vintage ·
  • Slim olive cargos by Uniqlo ·
  • Olive/brown argyle socks Vintage ·
  • Brown leather delancy boot by Ronnie Fieg x Sebago

4. Fall Festive

When shopping for a vintage blazer or suit, keep in mind you’ll have to bring it to your tailor.

It’s not uncommon to spend more at the tailor than in the store. For example, I picked up this Harris Tweed blazer for $10 and spent $50 having it altered (sides taken-in, sleeves tapered, and sleeves shortened).

With that said, the jacket should be fairly close to fitting – especially in the shoulders and the length of the body. You’re tailor is not a magician and paying him to recut the entire jacket defeats the purpose of finding a good deal.

Even if the tag is not your size, try it on!

Sizing varies greatly, depending on the brand, the year it was made, the alterations made by the previous owner, etc.

Brand new shoes? I know, not vintage.

Clearance sticker on the box? I know, awesome.

  • Tweed jacket Vintage ·
  • White shirt by Club Monaco ·
  • Beige winter jacquard sweater by GANT Rugger ·
  • White linen pocket square Vintage ·
  • Faded blue 484 jeans by J.Crew ·
  • Blue marled socks Vintage ·
  • Brown/Blue saddle shoes by Florsheim

5. New Suit, Old Accessories

Every vintage store has some kind of specialty. I have one spot for outerwear and denim jackets, one for sweaters and knits, one for scarves and ties, etc.

Don’t forget the accessories! They’re a great way to add a touch of old school character to a sharp, clean look. Here, for example, the suit and shirt are brand new but the tie, pocket square, socks and shoes might be older than I am.

There are so many tassel loafers in secondhand shops (for $30-50) that I’m not sure why people buy them new. It’s one of those styles that really hasn’t change over the years and actually looks better with a little beat-up character.

I picked up these at Buffalo Exchange, a quick-turnaround consignment shop in the East Village.

Finding a pair that’s barely worn is a steal – you’ll probably find yourself wearing them more often than your expensive dress shoes.

  • Blue gingham shirt by Gant ·
  • Grey wool tie Vintage ·
  • Blue/beige plaid pocket square Vintage ·
  • Blue striped socks Vintage by Tommy Hilfiger ·
  • Black leather tassel loafers Vintage by Johnston & Murphy
  • · Navy blue suit

Essential Worsted Suit in Navy

Good luck hunting and remember, thrifting’s a marathon not a sprint.

And, while we’re on the topic, this will make you laugh.

Much love,



Photography by Alex Crawford