How To Start Wearing Vintage Clothing

“How To Start Wearing Vintage Clothing”

I hope I find you well!

Hurdles at the Start of Wearing Your Vintage Clothing

Implementing your vintage personal style into your everyday garb can be daunting. Especially if how you feel and want to dress are dissimilar to how you currently dress. I know this from personal experience. I’d like to share what best helped me when I started wearing vintage clothing.

What I feel is best, is to first identify exactly what is making you feel uncomfortable.This discomfort can stem from not being accustomed to the way an outfit makes you feel.

I am grateful that generally, putting my vintage style on display and wearing vintage clothing comes easily to me. There aren’t too many accessories I enjoy utilizing that can make me feel uncomfortable. In fact I can only think of one combination and one accessory that does this. The lesser of the two being a heel, (particularly a stiletto), paired with a mini skirt. The sheer amount of leg exposed with the heel accentuating it can make me feel like a fish out of water.

Though most often, I’ve found that a lot of insecurity stems from the way you think people will perceive you.

The other item that causes discomfort, (a beast of its own, I must say): Hats. No, not baseball caps or sun hats at the beach. I’m talking wide brimmed fedoras, boaters and Edwardian inspired Cartwheels. I even have my eye on a particularly tempting hand blocked hat. That of which is inspired by the one that accompanies Audrey Hepburn in the opening scene of Breakfast at Tiffany’s.

I think these hats strike discomfort when sported because beautifully thought-out and crafted hats have become a thing of the past. They used to be as vital as a heavy coat on a winter’s day. One simply did not leave the house without a hat. (The history of hat wearing is actually quite interesting, but more on that another time perhaps.)

Essentially, the need and fashion for hats has since diminished. Thus making it a bit odd to wear hats, especially of the fancier manner. The only people you see regularly wearing hats now are Queen Elizabeth, and the Establishment; cowboys, hip trendsetters and those who have overcome the stigma of eccentricity that follows hat wearers.

For me, and I imagine many others, what makes wearing a hat so uncomfortable is the fact that it is at the top of the body. The hat is eye-level, and more than likely, is what will call attention to your person. People will notice your hat first, especially if it is of an unconventional style, (for your area and time period alike).

How to Start Wearing Your Vintage Clothing

So, while I deal with my own confidence-in-hat crisis, I have a few suggestions you might consider in order to make your transition into wearing vintage clothing smoother. 

“Ease” Into Wearing Vintage Clothing

When you first start wearing vintage clothing, what you need to do is ease into it.

Make a specified day of your week for a period of time where you wear an outfit of your vintage style, in full. Instead of having a “Casual Day”, have an “Embellished Day”. If comments from others is something you’re not quite ready to deal with, you can make your designated day on your weekend. I find that people who are regularly exposed to you are more likely to pass comment on your appearance; whereas the general public tend to speak up only to compliment you, and only if they’re outgoing. Once the nervousness of having eyes on you ceases to be an issue, you can then increase the amount of days you get to wear exactly what you want.

How to Start Wearing Vintage Clothing|Ardently Ana
I decided to start wearing vintage clothing two days out of the week, on a week day and on the weekend. This way, I can experiment with some styles and cuts that aren’t work appropriate. I’ve also decided that as the month goes by, I’d like to increase the amount of days I’m wearing my vintage and vintage replica clothing!

Accessorize and “Tread Lightly” When Starting to Wear Vintage Clothing

If the idea of a full outfit is intimidating, you could use a different approach. Instead of having a full outfit for the day, you could implement an accessory or singular article of clothing to your outfit. Wear a blouse that matches a pair of pants that you’re well acquainted with, or a pair of shoes with what others are accustomed to seeing you in, and that you feel comfortable in. Gradually implement new pieces into your usual and contemporary attire, until one day: Behold! Your vintage style is in full swing!

Start with Which You’re Comfortable In

If you’re not quite ready to sport the clothes that encompass your vintage style, one thing you could start doing is wearing the clothes in your current wardrobe that are most similar to your desired style. If you have a certain style of skirt you’re particularly wanting to wear, start wearing the skirts you do own.

How to Start Wearing Vintage Clothing|Ardently Ana
Start with which you’re comfortable in! I don’t find fancier, vintage-esque hats easy to wear quite yet, so I’m starting out with something contemporary.

The same goes with pants. If you want to start wearing wide legged pants, start wearing your pants, (or jeans), the few days before you wear the wide legged pants. Or say your goal is being comfortable in trousers, wear your most professional looking, long pant that you own. This will help you work yourself up to the trousers. The same would apply to tops. Say you want to wear a more structured top, or perhaps more frill, start wearing tops, (or even other articles of clothing), that have similar lines. Things that are perhaps a bit more boxy, structured, or frilly; so, when you work your way up to that piece you had in mind, it won’t seem such a drastic choice.

Now all that’s left is to…

Start Wearing Vintage Clothing!

            Another factor that can contribute to discomfort when wearing vintage clothing is when your style differs from your area’s general community, and/or when the community is not accustomed to diversity. A lot of the time, it happens to be both; and this is true for me. What has helped me pass this hurdle is having my identity in my clothing firmly grounded. Though this will be covered in a different post, (if it has not been already)! It also helps to think that your personal vintage style is part of what makes you, especially you. The real hurdle you have to get past is yourself. You are most likely holding yourself back with your worries and fears. The best advice I can give you: Start wearing your vintage clothing! You have to start sometime, and you can’t expect to break down your apprehension if you never make a start!

So, there you have it: My tips to help you start wearing your vintage clothing. I very much hope you found this helpful, and if you have any tips you’d like to tell me, please do so! I could always use some good advice.



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