How To Dress Vintage (Without Looking Like You’re In A Costume)

Toronto’s Maddie Dolegowski knows that buying vintage is good for your wardrobe, your wallet, and the environment. 

As the owner of Toronto’s Dear Hazel May, Maddie has proven that vintage clothing/jewellery isn’t boring, but stylish, well made and definitely affordable. She carries classic pieces from the 1940s to the 1960s that are high quality and always in style; she also features a large collection of jewellery spanning the 1920s to the 1970s.

SDTC: How do we wear vintage without looking like we’re in costume?

MD: Stay true to your own personal style. Know your era – wear what suits your body type. Don’t go overboard with all the extras – mix eras, add modern shoes and a modern purse. Wear your hair the way you would with anything else. Keep it simple!

How do YOU shop vintage?

Shopping for vintage is an adventure that can’t be planned. When I’m shopping for myself, I try to keep an open mind and not have too many expectations. You just never know what you’re going to find. I’m a true 50s girl, so I wear fit and flare dresses most of the time, with a few wiggle dresses mixed in depending on the occasion. If I love the fabric, and it’s a quality piece, but I don’t like the sleeves, I remove them. If something is too long for me, I shorten it. It’s not blasphemy to alter a vintage piece, as long as it’s done well.

My summer vintage uniform is very different from my cold weather vintage uniform, and I think the most important thing about shopping vintage for your everyday wear is paying attention to your lifestyle. Do you spend five days a week in an office? A well-tailored 1960s wiggle dress with a vintage cashmere cardigan works year round then, especially if your office blasts the A/C all day. Are you running around after your kids/dog all day? Try a fit and flare style dress; it takes less time and effort to throw on than a pair of shorts and a T-shirt, and looks so much more polished, plus the full skirt gives you more room to move. Look for vintage because it’s better quality, not because it’s a passing trend.

Where should we begin?

To dip your toe into the vintage world, start with whatever it is that you love most – jewellery, shoes, purses. It’s a familiar arena and you probably already have a style you go for. Get the original of that and bask in the superior quality.

Wardrobe staples:
Start building a base of quality pieces, be it a classic little black dress or a cashmere sweater in your most used hue. The cost per wear in the end will always make it worth it.

Treat yourself:
Buy that fabulous fill-in-the-blank that you cant stop thinking about. Even if you don’t have the occasion for it now, one day you will. And there is nothing better than knowing you have the perfect dress for that last-minute event.

What do you love most about wearing vintage?

I love that no one else will ever be wearing the same thing as me. I love the quality. I love the natural fabrics (less sweating!). But mostly, I love that it has a story, a history behind it and a past life.

Maddie’s amazing collection of vintage clothing, accents and jewellery will be featured at this year’s Toronto Vintage Clothing Show in the Queen Elizabeth Building at Toronto’s Exhibition Place, September 30th and October 1st. Wanna go? Tweet Hey @shedoesthecity! Hook me up with @416VintageShow tix for a fashion rewind!”

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