Dapper Day Part 2 – Decade Decision

Congrats! You’re going to Fall Dapper Day 2017 at Walt Disney World! Either your existing trip lined up with the dates, you live near the parks and are going to swing by for a day of vintage fun, or you’ve been inspired to travel down to dapper yourself up for the weekend. Regardless, it’s a win-win-win situation!

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So on to the next step: finding dapper inspiration. As easy as it sounds to “just find something retro to wear” is, I can assure you it is not easy. This is why we’re going to spend some time over the next few blogs helping you find that perfect dapper look.

As a 3 time Dapper Day veteran (impressive right?), here’s my process for deciding what to wear. I start with choosing a decade (actually, you should start by looking in your closet and seeing what you already have that could give you a dapper and vintage look. So, assuming your closet is full of FSU and Star Wars t-shirts like mine is, let’s get back to finding new dapper clothes).

Choosing a decade is a great place to start because it allows you to look across styles from the 20s to the 60s and see what works best with your budget, items you can use from your current wardrobe, the potential weather (no matter if it is fall or spring Dapper Day, spoiler alert: it will be hot or at least very warm), your personal style, etc. It also helps when searching for items because you know exactly what you’re looking for.

There are countless ways to find your Dapper Day doppelganger. For inspiration, you can check Google or Pinterest (the easy way), watch classic old movies such as Singing in the Rain or anything with Audrey Hepburn (the fun way), or by reading the section below with a brief overview of each decade (the TMSM way).

The 1920s

Ah, the Roaring 20s. Ladies, looks for this decade are mostly associated with flapper dresses, long pearl necklaces, fringy dresses, dropped waists, and Clothe hats. Fellas, recreate a 20s look with items such as tweed vests, newsboy caps, fedoras, or a pin striped suit.

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The 1930s

Dresses in the 30s left behind square or boxy shapes in the 20s Dresses were more flattering. Flowy sleeves and large collars are also a staple from this time. Cotton was not so popular as raylon crepe and silk were center stage. If you’re into wide cuff and high waisted pants, then guys, the 30s are for you! Fedoras and patterned ties also characterized the 30s.

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The 1940s

Ladies, think Peggy Carter. Dresses with shoulder pads, cinched at the waist above an A-line bottom. Basically, anything that will give you an hourglass shape. Floral patterns were common as were shirtwaist dresses. Got a pleated, A-line skirt? Pair it with a button down shirt and you’re good to go! Guys, think Captain America. Patterned button down shirts with high waisted khaki or brown pants. Sport coats and wide ties were in style too.

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The 1950s

Probably the easiest and most popular inspiration for Dapper Day, styles from the 50s can be spotted a mile away. Circle dresses, high waists, and sheath dresses are the best way to go. Also, check out rockabilly and pinup styles for a fun twist. When in doubt: if you saw it on I Love Lucy, you’re in the right place. Men can integrate the same high waisted pants from the 40s, but this time with a fun patterned twist. For a more casual look, bowling-style shirts were popular. When in doubt, if you saw Ricky wear it on I Love Lucy, you’re in the right place.Dapper Day Part 2 - Decade Decision 5

The 1960s

Things started to change in the 1960s. For the women, the early 60s were similar to the styles of the late 50s, the mid 60s brought that modern shift dress, Mad Men style, and the late 60s are the groovy flower child style. Each one is fun and dapper, but different. For the men, skinny ties, sweaters, and single button suits were all the rage.

For any decade, hats and gloves for the ladies were popular as well. In short, use this guide as a springboard to find the style that is perfect for you. You can’t go wrong!

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Latest posts by Susie Bryan (see all)

Susie Bryan

Susie Bryan has been a Disney fan since her family started going to Fort Wilderness on a regular basis when she was in third grade. Since then, her love for all things Disney has become a major part of her life. Susie has been a Main Streeter since 2015 when she worked for TMSM for her college internship. She currently works at a marketing agency and loves her job. She wants to live every day by her favorite Walt Disney quote, “All of our dreams will come true, if we have the courage to pursue them,” and her favorite Star Wars quote from R2-D2, “Beep, beep, boop, bop beep.”

Susie Bryan has 24 posts and counting. See all posts by Susie Bryan

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