How to Start Wearing Vintage/Retro Every Day

Lauren here —

As historic costumers, we all obviously love clothing, but many of us feel the divide between “costume” and “clothing.” Most historic costumers do not wear historic pieces every day, although these modes of dress are our passions.

So what *do* we wear every day? What are our “normal” clothes?

Several weeks ago, we attended Rufflecon in Stamford, Connecticut. This event is an “alternative fashion conference” but focuses primarily on Lolita fashion and its offshoots. For those unfamiliar with Lolita, here are some examples:


In talking with many of these women, I found that a lot of them dress this way every day, despite the flack they get from muggles. This is their identity. This is what they are comfortable in and how they express themselves through dress. Their outfits (“coords”) are not costumes, but clothing.

This got me thinking about other modes of dress considered alternative. The one I connect with the most is vintage and retro fashion. I know plenty of men and women who dress in vintage or retro styles every day (Dandy Wellington, Terra, Rachel, Missi to name just a few), and I can finally include myself in this group, but only after….well, an effort.

An effort? Yes. I didn’t just suddenly start dressing this way one day and never looked back. It took a conscious effort because I consistently felt “in costume” when I wore these clothes, not like I was wearing my normal, everyday attire. Not comfortable. Not relaxed. This is not to say that I do not feel comfortable in full 18th century regalia. What I mean is that we often feel we are”on” when in costume, whereas when we are just dressed, we wish to feel ourselves rather than a character we are portraying. One state is not superior to the other; they are just different.

My almost-everyday look – Freddies jeans, a t-shirt, round sunglasses, and a B&T headscarf.

So how does one go about transitioning to a mode of vintage or retro fashion every day? Here are some tips, based on the experiences I had (and still have) in back-dating my wardrobe and changing my psychology:

1. Recognize that it is OK to be different and that you want to be different. This is not about fitting into a certain group or dressing how you think someone else will like you – this is about you, being comfortable in your own skin, and expressing your true self to the world.

2. Get rid of everything in your closet that doesn’t make you feel good. Try everything on, and donate or sell anything that doesn’t fit. Donate or sell anything that you don’t feel yourself in. Be brutal – don’t allow yourself to say “oh, but if I just lose 10 lbs I’ll fit into that.” No. Dress for who you are now. It’s amazing how good you feel, no matter your size or shape, when you wear clothes that fit you.

3. Now that you have a clean slate, purchase or make a few items you love. Really love. And that fit you well and make you feel great. Go for the types of clothing you like and wear the most – for example, I wear pants every day. I love dresses and skirts, but if I’m being really honest with myself, I only wear them when I’m “dressing up,” not for my day-to-day clothing.

Simple looks are the easiest to start with – trousers made by me, blouse is from a thrift shop, wool beret is from Amazon. The most “vintagey” single part of my outfit is my shoes, oxfords from Restricted, but the whole effect is bohemian without being accurate 1930s head-to-toe.

4. Mix it up. With these first few items, mix them in to your existing wardrobe. This is the transition – ease into it. The idea is to train your brain to feel that these new clothes are everyday, normal clothes, not a costume. Get used to and comfortable with how you look to yourself, the attention you may get from other people, how you feel in your clothes, etc.

5. Support your key pieces. Something I found when I started wearing high-waisted trousers was that most of the rest of my clothing just didn’t work with them. My sweaters were all too long, my t-shirts were all too tight, even my underwear wasn’t the right shape anymore. This called for action – I shortened all of my sweaters, culled my shirts, and bought new undies. The result? Now ALL of my clothing works together, and it’s easier than ever to choose a vintage look in the morning.

6. Realize that you may never go back and that’s OK. Once you change your mode of dress completely, and you get used to it, you may find that putting on your old, modern clothes becomes detestable. Even if I wanted to wear modern low-rise skinny jeans, the feel of them squeezing my lower half to death is too much for me to bear. I’ll never go back. And that’s OK.

It gets easier, then it becomes the norm. The real you comes out and you feel at your best. The day I wore this outfit, a gentleman said he liked my costume. I said, “this isn’t a costume! These are my clothes!”

At this point the journey is complete. The new “norm” is the vintage/retro and modern outfits no longer appeal. I now feel like a “poser” when I try to wear modern, “cool,” expected clothing. And even though my everyday style gets attention, I don’t feel like I’m wearing a costume. Instead I just feel myself. Mission accomplished.

The moral of the story is that you can and should dress any way you like, but it takes some getting used to. You don’t have to “dress up,” every day. You don’t have to wear what you think is expected. You don’t have to do a full, head-to-toe look every single day. Start small (a headscarf, for instance), ease into it, and find what’s right for you.
Favorite Shops for Vintage/Retro Clothing:
Unique Vintage
Emmy Design Sweden
Vecona Vintage
Freddies of Pinewood
Vivien of Holloway
Fab Gabs on Etsy


  • Cassidy

    November 1, 2016 at 9:42 PM

    That's very much how I feel! Although the two of us go for different decades. 😀

    (I am definitely going to try that sweater alteration one of these days.)

  • Arlene

    November 1, 2016 at 9:42 PM

    Excellent advice! Transitioning is the best way to go and in the end you will love your clothing pieces all the more as they were chosen over a period while you developed your retro fashion style.

  • Juliana

    November 1, 2016 at 11:28 PM

    This post is awesome. I started in vintage/retro very much the way you describe, and while I was into it for several years, I find myself moving to another aesthetic, but still can't manage modern clothing any longer. I find the transition periods are the hardest, because you are still trying to "find" yourself sartorially, and that is difficult.

    Your clothes are so fabulous!! I love the outfits you chose to share with this post–so chic and lovely and also uniquely you.

    • Lauren Stowell

      November 7, 2016 at 10:58 PM

      Thank you! Yes, that's an important point you make as well, that your fashion isn't fixed. It will change and you might drift away from vintage/retro to something else, but that's all OK. It's all self-expression and it reflects who you are at that time.

  • Jessica

    November 1, 2016 at 11:58 PM

    I think this is wonderful advice for anyone, whether or not you belong to a particular subculture that tends to dress a certain way. Clothes that fit! Clothes that feel like "you"! That's so important, and I feel like too many people neglect that.
    Zella Maybe

  • Esther

    November 2, 2016 at 12:34 AM

    Love this post!!!!! I agree with all of your points, and really, even after a couple of years of making the transition, you find more and more what you are truly comfortable with. For me, I like dresses and outfits that are comfortable, and don't require constant fiddling. The possibilities are still endless, it just helps me to truly love what I wear, rather than feeling uncomfortable (literally and figuratively), just as you say.
    Thanks for the post! I love that you are wearing vintage fashion every day now; isn't it fabulous?!! You look lovely in it!! 🙂

  • Unknown

    November 2, 2016 at 12:41 AM

    Hi Lauren,
    Long-time lurker here….I love the post on retro dressing every day, and totally agree!
    Thank you for sharing your tips & tricks.

    I too, deeply desire to dress in non-modern clothes.
    Do you have any advice for those us who want to dress from another era, but are challenged by an active/modern lifestyle?

    My story:
    At one point, I was doing well with a mid-60’s look: lots of pencil or full skirts w/ballet flats, and LOVED IT.
    However, due to weather and lifestyle (commuting from Oakland to SF without a car) my wardrobe eventually morphed into a more “active” look…it was an ugly, slippery slope…
    I started wearing Nikes instead of ballet flats for the aggressive running/walking to and from public transportation.
    Then, I started wearing leggings under my skirts for the same reasons. Legging were soon switched out to running tights, as I wore out the seams too fast :/
    At one point, I used to change shoes & things once I got to work and before I left for the day, but even this practice went away as my schedule (and weather) became more unpredictable and hectic.

    Then, I moved from the Bay Area to Portland OR, where I still commute without a car (via train, walking and now A LOT of biking)
    Next thing I knew, all my lovely “retro” garb was deep in a drawer, replaced by mini sundresses with running tights & shoes.
    This is now my primary wardrobe.
    And now, hoodies are a must because OMG so much rain and this just makes me sadder :/
    As the temp gets colder (my first time living in these things called ‘seasons’) I’m even further at a loss for how to dress with historical flare while fending of the cold, wind and OMG did I mention the rain?!?!
    I can’t even wear my beloved cat-eye make-up because it just gets rained on and ruined.

    I miss my retro style so much, and don’t really feel like 'me' anymore.

    Again, thank you for your post.
    Such good advice about “getting rid of everything in your closet that doesn’t feel good”….great place to start.
    Guess I’ll have to get creative and find my Retro Way once more 🙂

    You're Awesome. Thanks for reading this!

    • Myrthe

      November 2, 2016 at 9:26 AM

      The whole commuting story sounds very familiar :). I live in the Netherlands, but I also bike & take a train to work every day. Including rainy & windy days. I do, however, wear skirts nearly every day and in all weather. It can definitely be a challenge to find clothing which both fits your style and is practical/warm enough for daily life, but I do believe it can be done! Start with those pieces which work for commuting, I for instance always wear a cotton petticoat with my skirts instead of a tule one because that gets stuck in my bike wheel. I wear t-shirts and thermo shirts underneath blouses or sweaters to fend off the cold. I have one pair of vintage ('70s I think) low ankle boots which I love because they work with a skirt and rainy days. Little things like that can go a long way. I compromise with my rain coat, which is modern but definitely a necessity ;). And after all, I take it off once inside so it doesn't matter as much that it doesn't match. I'd say start by finding something practical you do like, and build from there, because it definitely can be done!

    • luckyratfoot

      November 2, 2016 at 8:42 PM

      I kind of feel like you do. I don't have to use transit but my lifestyle is kind of weird and hard on clothes. Way back when I was in high school I wore lots of fancy clothes because I mostly walked around and sat at desks. But now I work at a public library. I still sit at a desk a lot, but I'm carrying stacks of dirty books and getting on my knees a lot. I also just finished school (for now, going to go back in a year) and ended up getting a second job as a production potter. So no fancy clothes there! Style-wise I don't feel like "me" anymore either. The past few years I have noticed a couple places in my life that vintage would work. A couple times a year I need to wear a nice dress, and the past two summers I have gone on beach vacations and had nothing to wear. Perfect opportunities for capsule wardrobes! I have made one dress so far for my slightly goth-1950s goin' out wardrobe. Not sure about the beach things yet though.

    • Anonymous

      November 2, 2016 at 10:52 PM

      I can sympathize over the grit and grim of working in a public library…believe me. I find vintage to be less an issue than any wearing of white since inevitably that's when I have to change the copier toner or deal with filthy,spider ridden books. As long as you have a decent range of movement,ie the shoulders aren't too tight and you can bend over, vintage should work as well as modern dresses. I prefer the fuller vintage and/or repro skirts since you can crouch down and still have coverage. Also since a lot of vintage stuff is natural fibers, it breathes better than much modern clothing. Good luck.
      Heidi in Los Angeles

    • Lauren Stowell

      November 7, 2016 at 10:54 PM

      Hi Kathleen – I totally agree with the previous comments. Great stuff! To add my two cents, I would start with studying up on what women in the vintage decades wore for the same reasons. Original, complete catalogs are great places to research this. They contain so much more than just dresses – gaiter boots, overcoats, long underwear, etc. I actually have an entire mini-catalog from the 1920s JUST for long underwear (for the whole family! lol).

      The second thing that comes to mind is that it sounds like you're forgoing the retro look because you're associating it only with dresses and heels. Instead, think of trousers and tennis shoes (Converse All-Stars have been around in pretty much their original form since the early 20th century). None of your clothes have to fit tight – for instance, I actually have way more range of motion in my Freddies of Pinewood high-waisted jeans than I have in modern skinny jeans, and combined with simple Converse tennis shoes, there's nothing active I can't do.

      Rain got your makeup and hair all wacky? For the makeup, if cat eye is your thing, make sure the ink/gel/pen/pencil is waterproof, and that goes for the mascara too. World of difference. For the hair, embrace the power of the hat or head scarf. A cloche hat is probably the best ever head covering for a wet day, because it completely covers the hair, but a newboy cap or a wool beret are also fantastic. I understand that a lot of workplaces don't allow hats, so if this is the case, I'd probably brush out my pincurls, then *roll them back up loosely*, tuck under a hat, scarf, or one of those cute vintage style rain hoods making a comeback, and then let the curls down again with a quick brush once I got to work.

      Just some ideas. The fun part of this is researching how women dealt with the weather and activity in the past, and find the methods that will work for you.

  • kashurst

    November 2, 2016 at 6:29 AM

    I dress in vintage and retro frequently. 40s, 50s, 60s- it's all fun and I always feel like me! But I can also rock a modern style with skinny jeans and all. Heck, I even frequently wear an Indian salwar kameez. Like you say, I just want to feel like "me." I don't want to have to stick to one style and that is perfectly acceptable. The minute you start wearing clothes because you feel like you have to in order to be acceptable (because of size, or style), you lose yourself.

  • Amoris

    November 2, 2016 at 1:36 PM

    I love that you used Lolita fashion as an example of "costume" as "normal" clothing. That has such a personal connection for me! I started delving into alternative fashions when I was ~18 and fell in love with the Lolita look. I wore it on a daily basis to college, and I quickly learned the difference between a "dressed up" outfit and a practical, daily one. But even my daily outfit always had a blouse, a petticoat, nice shoes etc. I loved it, but it attracted a lot of attention. Mostly positive, luckily, but that did make me almost immune to stares & whispers. I moved on from Lolita to more vintage styles, and when I wear vintage/retro clothing now, even with a petticoat and all that, it doesn't attract nearly as much attention as Lolita used to do. I don't even really notice it anymore.
    So that's also a way to go at it: start as extreme as you can imagine, then everything after that will be easier 😉

    • Lauren Stowell

      November 7, 2016 at 11:02 PM

      Yes, absolutely! You're "braver" than most – it takes a lot to dress very different from the "norm," but as you say, starting there and coming back from it will be a snap.

  • Ms. Rebecca

    November 2, 2016 at 2:05 PM

    I love vintage fashions from the 20's and 40's, but my heart truly lies in the Victorian and Edwardian eras… I don't know that I could go whole hog the way women such as Sarah Chrisman has. Wearing a full hooped skirt on a daily basis may be a daunting task. I fight with myself constantly about it. I finally gave up the fight and am now designing a handmade wardrobe with fashioned inspired by these times. I can use the styles and design elements to create a style all my own.

    • Lauren Stowell

      November 7, 2016 at 11:03 PM

      I think that's awesome! Working the Victorian elements into a more modern (well, more modern than Victorian, haha) silhouette is really cool, and also very vintage. There's all kinds of vintage historicism in 1920s, 30s, and 40s. Blending the silhouettes and details is super fun. I can't wait to see your designs!

    • Anonymous

      June 16, 2017 at 2:16 AM

      My winter work clothes are almost exclusively Edwardian-inspired. Long wool gored skirts with coordinated tweed jackets and lace-up boots. I do wear turtlenecks instead of blouses, because even a tweed jacket is not enough to keep me warm in the Midwest in winter. Admittedly, I work in a library, so there's no rigid dress code, but no one acts like I'm weird, either. (New hires do tend to double-take when the weather gets warm and I switch to 30's-inspired skirts and short-sleeved sweaters–visible limbs!) But anyway, what I mean is: go for it!

  • MrsC (Maryanne)

    November 3, 2016 at 8:24 AM

    Bless and good on you. I don't really dress retro-vintage but i have no time for fashion, as it has no time for me. My wardrobe is decreasing in quantity and increasing in quality, and nothing in it will ever be seen in a shop. But that's why we sew yeah? 🙂

  • Rowenna

    November 3, 2016 at 3:41 PM

    World's lamest problem: I keep inching toward wearing more vintage in my everyday life (I prefer skirts and dresses) and then backing out because I'm cold. All the time. Silly, right? So…vintage with fleece-lined leggings, perhaps? 😛 Right now it's more touches of vintage–block heels, a big brooch, hats, overcoats…and it's something to look forward to summer for! I love this advice, especially just owning it and getting comfortable both mentally and physically.

    • Sue

      November 6, 2016 at 5:29 PM

      Hi Rowenna, you need to make yourself a long, brushed cotton, (organic if possible) full petticoat. The reason why vintage often looks 'wrong', particularly in drama series, is because the underwear isn't right. It is only relatively recently that people began to travel in heated cars. Riding on a motorbike or horse in the Winter can still give the modern traveller an appreciation of what dressing for the outdoors is all about. Study up on undergarments and think layers, also capes and gloves and scarves and shawls. I have about 6 layers on when I go out this time of year. All the very best from chilly Normandie, Sue

  • Cate

    November 3, 2016 at 5:17 PM

    Fantastic post and brilliant for anyone who's nervous about taking the leap. As someone who wears vintage every day, I feel incredibly odd putting on 'normal' clothes. Most of it irritates the hell out of me, the cut is never right, the fabrics are horrid and things often look cheap because they lack the lovely detailing of vintage clothing. I still struggle with the attention it brings, but I tend to adapt my outfit to the situation, so rarely go full on, top-to-toe when I'm just popping to the supermarket! xx

  • albinomonkeyc

    November 4, 2016 at 5:04 AM

    Having been a long time wearer of Lolita (not as often as I should but reasons!!) I find that it gives one a certain confidence to wear just about anything out in public. The transition from cupcake poufy skirt to pillow around your bum skirt becomes as natural as sleeping. Here the real bits though: you will get stared at, you will have people ask you about it, you may have douches take pictures of you w/o your permission. That is the reality. Just be comfortable in your clothes and nobody can say anything.

  • Nicole

    November 6, 2016 at 8:31 PM

    I totally get you on the feeling like a "poser" when you are wearing modern clothes. 🙂 I wear some modern clothes, but I style them in a vintage way most of the time, and when I don't, I feel strange- like "what am I doing in these foreign garments?" You have some really great advice in this post- I love it!
    The Artyologist

  • Rebecca

    November 7, 2016 at 4:52 AM

    Loved this post! I'm rediscovering my sartorial self and desperately trying to break free from that "new mom" style rut. (My daughter's three now so I'm long overdue!) Comfort and quality are priorities these days, but that joy of dressing for self-expression is what I really miss. Thanks for giving me that push in the right direction so I can ease into a new stylish and *functional* wardrobe for every day.

  • Lauriana

    November 7, 2016 at 3:06 PM

    I gradually eased into wearing mostly 1950's inspired clothes a few years ago and I don't think I would ever go back to wearing low-rise trousers (those were never comfortable for me anyway) but recent changes to in my life (a new job and much more sport) have put my chosen style in a state of flux once again.

  • Unknown

    April 10, 2018 at 3:52 AM

    I am wanting to ease into Victorian clothing but I feel so nervous. I am going to get a few statement pieces and try and wear it out in public.


Leave a Reply