6 Tips for Buying Vintage Clothing and Accessories You’ll Actually Wear

Shopping for vintage clothing and accessories can be a great way to score some unique pieces and learn more about the history behind the clothes that your favorite brands make today. But everything about shopping vintage — from figuring out where to look to determining what’s worth buying — can be confusing for guys who haven’t acquired many vintage pieces before.

Luckily, the principles are relatively simple. Read on for some simple guidelines on how to make the most of an excursion to the local vintage shop. With a little bit of luck, and a healthy measure of patience, you’ll find some classic clothes and accessories that integrate well with the other pieces in your wardrobe.

1. Do your research to find the best spots

vintage clothes

Do your research to make sure you are buying quality vintage clothing. | Caroline McCredie/Getty Images

If you have a friend or an acquaintance in your city who’s always dressed in the coolest vintage pieces, take advantage of the opportunity to ask him about the best shops in your area. If you don’t know anyone with inside knowledge of the best vintage shops, then some online research can likely point you in the right direction. Sometimes, the best shops carry clothes and accessories from a wide range of decades, and other times, they’re very specific, often thanks to the owners’ own interests. Additionally, estate sales can be a great way to find some awesome pieces, since clothes sold at them have often been stored for years. Flea markets and auctions can be promising sources.

2. Remember to prioritize fit

Photo by Matthew Lloyd/Getty Images

If you only need minor alterations, go for it. | Matthew Lloyd/Getty Images

When you find an amazing Harris Tweed blazer or military peacoat at an amazing price in your local vintage shop, it can be tempting to make the purchase, even if you know it’s not quite the right size. If an entire garment will need to be reconstructed for you to actually wear it, then it’s better to be realistic and pass on the purchase. On the other hand, if a garment would only need minor alterations to become a piece that you’d love, then it may be worth the cost.

3. Buy classic pieces

classic vintage apparel

Always go classic, what other point is there to buy vintage? | Matt Cardy/Getty Images

A vintage shop may be fun a place to marvel at novelty blazers and outrageously-printed shirts, but it’s always a good idea to choose classic pieces. Look for silhouettes that are timeless and fabrics that fit in well with the clothing that you already wear. Additionally, it’s good to keep in mind which garments and accessories are classics for you. You may love 1960s repp ties that would be too loud for a man with different taste, or you might love plaid Pendleton shirts that would look like a costume on another guy. Always keep in mind what you already like and wear regularly to avoid buying pieces that you like in the store but won’t actually wear in real life.

4. Decide what’s worth fixing

button and eyelet of a pinstriped jacket

Simply replacing buttons is totally worth it for something truly original. | iStock.com/ ClaudioVentrella

When a piece of clothing or an accessory is several decades old, even if it’s in great condition, it’s quite possible that it will have a minor flaw or two. If you look hard enough — as you should, when inspecting a piece before purchase — you may find a seam that’s beginning to come undone, or a button that’s cracked or gone. In either case, the piece is likely worth fixing if it’s something you’ll enjoy wearing regularly. On the other hand, the same rules you use to determine whether a garment is worth altering for fit issues still apply if major repairs need to be made.

5. Pay attention to styling

vintage hats

Make sure the cut goes with your regular style of clothing so it’s easy to pair. | Odd Andersen/AFP/Getty Images

When you’re standing in a vintage shop, debating whether the piece you’re looking at is something that you can pull off, remember to consider how you’ll style the item. If a piece fits well and is made in a relatively timeless silhouette, you can likely figure out a way to wear it with other pieces in your wardrobe, without making it obvious that the piece is decades-old. A winning strategy is to wear one vintage piece with an outfit comprised primarily of your usual uniform.

6. Know what you’re looking for

Man wearing a dress watch

If you’re new to the vintage game, start with accessories. | iStock.com

If you’re new to vintage shopping, figuring out where to start may seem like an impossible task. So when you’re first beginning, choose a piece of clothing or an accessory that’s known for being easy to buy vintage, or better to buy used than new (Think classic wool outerwear, cashmere sweaters, cufflinks, and watches). If you’re looking for something specific, do your research ahead of time so that you can determine whether what you’re looking at is authentic and high-quality. If you want to avoid paying top-dollar for the most well-known brands, do your research on lesser-known brands that offer similarly high quality. And make sure that you’re familiar with a company’s sub-brands and diffusion lines so that you’re sure to know what you’re getting.

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