Have you ever felt sure that you belong in another era (at least, in terms of fashion)? Have you ever seen someone rocking a massive circle skirt with pin curls and thought “ugh, teach me your ways”? Well good news, friends: I’m here to teach you the basics of dressing in my favorite manner: that is, how to dress dapper.

The timing of this article is no coincidence: if you live near Disneyland or Walt Disney World, you might be aware that the next two weekends are going to play host to my favorite holiday of the year, Dapper Day! 

Dapper Day began as a chance for Disney fans to dress in the styles people would have worn when Disneyland first opened. Since then, it has grown to include dressing in your dapper vintage best from any decade, or even taking it one step further and “Dapper Disneybounding” as your favorite character. (See our article on Disneybounding for more info on that.)

Whether you’re attending Dapper Day or would just like to get some beginner’s info on how to give your wardrobe a touch of retro glam, read on!

Table of Contents

The Basics

Products: Petticoat – ModCloth, Sunglasses – Unique Vintage, Black Heels – Unique Vintage, Pink Shoes – Pinup Girl Clothing, Earrings – Unique Vintage, Gloves – Unique Vintage

If you want to look like a vintage princess, here are the easiest accessories that will give your outfit a boost. 

Petticoats are lovely and elegant and give your skirt or dress a beautiful, full silhouette. (They’re also super fun to twirl around in.) Heels are a good idea, but for a vintage feel, opt for retro Mary Jane heels or pastel kitten heels instead of sky-high stilettos or wedges. 

Pearl accessories and sleek cat-eye sunglasses add elements of vintage glam, and gloves are my favorite finishing touch. There are even some gloves that come with pads on the fingers so you can still use your phone.