Dressing Vintage: Simple Tips to Avoid Looking Costumey

Hi there!

I was pondering last night, in retrospect of some sweet comments, what sort of things I do in order to avoid looking too costumey when wearing vintage or vintage inspired clothing.


Casey of Casey Maura

There’s a lot of misconception out there on vintage or retro style. Many people think they can’t pull it off.  Others are afraid they’ll look out of place, or draw too much attention to themselves.  And still others are unhappy with their total look because they feel too much like they’re in fancy dress or costume.

We all have those random days when things don’t come together quite as well as we had hoped, but here’s some simple tips from me on how to not look costumey when wearing vintage or vintage inspired clothing.

Disclaimer:  If you prefer to look costumey that’s totally FINE, too!  Dress how feels good to YOU!  I don’t judge someone for what they wear. The great thing about living NOW is that we get to chose what styles and fashions we most enjoy!

Here’s just a few things *I* do when I dress vintage.


Me wearing a vintage 1940’s suit

Decide if you want to do authentic vintage fashion (a head to toe period look) or vintage inspired fashion (adapting or mixing vintage with everyday clothing).  

For me, those are the top two ways I see vintage fashion worn.  There’s no right or wrong answer here- it’s all up to you and what you want to do with your look.  If you’re going for head to toe period- it’s time to dig into those original period sources.  If you’re going for a vintage inspired look, let overall aesthetic be your guide.


Katherine of The Fashionable Past, Ginger of Scene in the Past, and I at Costume College a few years ago. 

Dress for Your Personality, Not Because You Think It’s “Right”

In the way you’ve dressed previously, what have been your favorite looks?  Chances are, if your past style sense had a general “feel” to it, you can find an equivalent in vintage fashion.  Are you a tomboy?  A girly girl?  Avante Garde artist?  Sensible and practical?  A career woman?  Well, regardless of what your lifestyle is, chances are there’s a vintage equivalent to you.  1920’s girls didn’t all wear fringe, 1930s girls didn’t all wear bias cut gowns, and 1950’s girls didn’t all wear poodle skirts.  So go poke around online (I suggest pinterest), and if one look grabs you instantly as something you would wear in real life, add it to your pin board.  There’s no real “right” or “wrong” way to dress in an era, because there were so many different styles in every single decade.  In fact, old magazines suggested you dress by “type”, just like fashion magazines of today.


Me wearing 1930’s style last summer.

Chose Your Hosiery For Your Outfit

There should be a sort of overall aesthetic to your look, so chose your legwear (or not) accordingly.  Maybe you select nude seamed stockings, which gives a little extra dimensions.  Perhaps people won’t even realize you’re wearing seamed stockings if they’re nude on nude, but it will just look *interesting*.  Harmony, simplicity, and cohesion work well here.


Casey of Casey Maura– a woman of exceptional style.

Select a statement piece

What’s going to speak the most out of the outfit you’re wearing?  Is it your dress print?  Your crazy novelty pin?  Your bakelite bangles? Your crazy hat?  If you have a piece you really want to be noticed, plan your outfit around that specific piece.  If in doubt, keep it simple.  A solid background for a statement brooch always looks classy.  Sometimes red lipstick is enough of a statement in itself.


Me at a living history event in San Diego.  I’m wearing trousers, a comfy blouse, flat shoes, and sunglasses, because I knew I was going to be active that day.

5)  Make it Livable

How do you feel when you’re wearing your outfit?  Do you feel like yourself, or do you feel like you’re dressing as someone else?  Are you self conscious, or are you confident?  Our clothes can do amazing things for us.  But they can also make us feel out of sorts.  For example, I can’t wear high heels or I’ll trip over myself.  If you’re thinking about a single article of your clothing more than you are what you’re doing or enjoying the company you’re with, maybe it’s time to re-think that choice. Sometimes it’s as simple as adding insoles or heel grips to a shoe, or holding a hat in place with a hat pin, or finding a lipstick that doesn’t go all over the place when you eat (and how do we always get it either on our chin or on our teeth?  Ok, maybe it’s just me).  It sometimes takes time to find what works for you, and that’s ok.  Even if everyone else raves about a particular maker or style, it’s ok if you decide it’s not your thing.


My friend, Katherine Brookes, always has impeccable vintage style.

Find Flattering Hairstyles

One you’ve got one you’ve found that works for you and your face shape, you’re good to go.  It’s ok to do it over and over, or variations on that hairstyle, if it works.  Like clothing, there’s no “right way” to do hair for any given time period.  Check out photos of real people if you’re intimidated by the super polished looks you see other bloggers, or movie stars, wear.  Not everyone needs to have perfectly polished victory rolls to have vintage style.  And if you’ve got a flat spot, just add a hair flower or hair ornament, or hat.  People will think it’s intentional.  Really.


My friend, Simone (of The Wardrobe Mistress on Etsy).  Photo by Gordon Ayres


Some people can pull off the super dramatic makeup or pin-up style. I can’t.  My old standby for makeup is red lips, nude eyes with medium brown crease, and maybe eyeliner if I’m feeling adventurous.  And if you aren’t comfortable with red lips, that’s totally ok!  There were a variety or reds, pink, and corals that were worn through many different vintage decade.  I often wear a lip stain instead of a lipstick, even when doing daily vintage inspired looks, and you know what?  It totally works.


Beth of V is for Vintage.  Always expertly fitted, always tasteful in accessories.

Select Clothing That Fits Well

This is probably not something that comes up too often on style tips for a reason.  If you see sets of wrinkles going across any part of your body, it’s probably too tight.  If it doesn’t hug your curves or if it droops, it’s probably too loose.  Find something in the middle and the fit is just right.  There’s not much we can do about too tight vintage, but you can do something about a piece that’s too roomy.  You can either take it in yourself, or go to a tailor and get it altered to fit you perfectly.  It is an extra step and sometimes an extra expense, but it’s SO worth it to have clothing that fits you just right.  If you’re not sure where to find a place that does alterations, ask a local dry cleaner or do a search for alterations in your area.  And if it’s vintage, make sure you tell them to not cut out the extra fabric that’s there after the seams or hems are taken in- there may be a time you want to let it out later!


Me, pretending to be fancy.

Embrace Your Good Points

We all have things we don’t like about our appearance or body type, but instead of festering about that, why not turn that around to something positive?  What’s something you LOVE about the way you look?  Do you have a tiny waist?  Emphasize it!  Great décolleté?  Wear more boat necks.  Long legs?  You can look tall and elegant in trousers and knee length skirts.  Pretty hair?  Add ornaments some pretty comb or flowers to your hair.  Love the color of your eyes?  Wear colors close to your face that bring out that color.  Underplay the points you don’t like, emphasize the ones you do like.  And if someone pays you a compliment, don’t tell them what you don’t like about yourself or your look- just kindly say “thank you!” and give them a big smile :)


Me at the Huntington Gardens

Be Confident!

Once you’ve selected your look for the day, embrace it.  Don’t fuss in every mirror.  Don’t wonder if people are looking at you.  If people compliment you, give them big smile, look them in the eye, and thank them.  If they ask you funny questions “Are you in a play?”, ask “What’s the occasion?”  or ask a question or make a comment on your style, just be kind back and tell them you just like to wear vintage styles.  Most people are just curious, and some may even want to take up the look themselves!  Don’t take every notice as something negative.  Feel good about your choice, and just keep on enjoying your life.  Confidence and happiness are contagious :)

(Revised 2022)

37 Comments on Dressing Vintage: Simple Tips to Avoid Looking Costumey

  1. Desiree
    September 9, 2014 at 1:07 pm (10 years ago)

    Whether you wear vintage or not, some of these tips are for everyone, especially picking your good points, focusing on just one feature on face, etc. Nice work :)

  2. Jill
    September 9, 2014 at 2:09 pm (10 years ago)

    Wonderful post!

  3. Fiona Timantti
    September 9, 2014 at 2:19 pm (10 years ago)

    Some good points here. But if ‘crazy’ is your style, i say go for it. Not everyone is that toned down and still look gorgeous and not too ‘costumey’. Quality and fit of your clothes are the most important thing in my opinion. And i have few pairs of wonderful ff vintage nylons with dark brown seem, i love them! :)
    p.s.Your blog is marvelous!

  4. Perdita
    September 9, 2014 at 2:37 pm (10 years ago)

    I couldn’t agree more, especially number 1 and 2!!

    My tip would be: surprisingly few ‘real’ women in the 40s had victory rolls every day, in the 50s had full Marilyn make up, in the 60s had a Sassoon bob and Twiggy eyes. There seems to be an obsession with massive hair and loads of red lipstick when in fact that would be like (in 50 years time) someone in ‘vintage’ day clothes doing full Kardashian-at-an-awards-ceremony face and hair.
    As you say, many many women had simple hair and more subtle lips/eyes. In fact it was usual.
    Every time I see a tutorial which insists everyone had foot high hair and glossy red lips I roll my eyes.

  5. Tegan
    September 9, 2014 at 2:40 pm (10 years ago)

    I’d also add in to be aware of your setting. If you’re going to an informal coffee date and you wear a ballgown, the fact that it’s vintage or modern isn’t what is going to make it feel like a costume! Fashion plates mostly talk about evening wear, so look to ads, old photos, and other vintage-lovers to get a better sense of day-to-day wear. I know when I think 1930s, I think slinky bias-cut gown. But 95% of the time women wore something other than that. And it can be easy to forget when the pretties are SO PRETTY. :-P

  6. Green Martha
    September 9, 2014 at 2:59 pm (10 years ago)

    So many good points ! I don’t do vintage, but I feel your points could be translated for earlier periods as well.

  7. Stephanie
    September 9, 2014 at 4:24 pm (10 years ago)

    This is a great post! :D I particularly like your points about makeup. I have a very basic look that I do almost everyday- a nude eye with a small winged eyeliner, a soft peach or coral blush, BB cream and a pink or coral lipstick. I’ve pretty much sworn off reds except on special occasions because they are so high maintenance! Nothing screams over the top costume-y to me like crazy over the top, way heavy make-up (except maybe wearing a ball gown to the grocery store.)

  8. Miss Kittu
    September 9, 2014 at 4:34 pm (10 years ago)

    I loved it! Great photos- very fun to read,

  9. Susan Robertson
    September 9, 2014 at 4:57 pm (10 years ago)

    Love this blog…first time I’ve seen it. I love 20’s fashion and get inspiration from “Miss Fishers’ Murder Mysteries” on TV here in Australia. I think you can see it in the US. Phryney Fisher has such effortless style……watch it if you’re a fan of that era.

  10. Alexis
    September 9, 2014 at 5:20 pm (10 years ago)

    Thank you for the wonderful post. I wore my first vintage dress to a couple of weddings a few weeks ago and it was great! I was comfy and confident. I do agree that wearing something that fits and you don’t have to keep checking is the best. Took notes when reading this too and will be buying more vintage garb for my wardrobe!!!

  11. Annette Baker
    September 9, 2014 at 6:13 pm (10 years ago)

    Well done! I bet you hear this too. ” I love your style, but I could never pull it off”. You have now given me an answer to that excuse. I have been wearing, selling, up cycling and sewing vintage for 40 years. What a classy guideline for the joy of vintage dressing.

  12. Charlotte
    September 9, 2014 at 6:15 pm (10 years ago)

    Thank you! Lovely post, and all such lovely women!! XOXO

  13. Cindy kitchell
    September 9, 2014 at 8:42 pm (10 years ago)

    My goal is to wear vintage every day. I mix and match new and vintage. I have been collecting and wearing for over 40 years. Love you blog. My suggestion is to find a good dry cleaner and tailor that respects vintage and have your stuff taken care of properly. I am one of those dry cleaners. If you need any questions answered shoot me an email. Keep doing what your doing its great work.

  14. Lynne Connolly
    September 10, 2014 at 2:43 am (10 years ago)

    Just had a vintage hair style & any little dress completes the look… It’s fun to do that every now & again ****
    Great blog X

  15. isabel
    September 10, 2014 at 3:15 am (10 years ago)

    Well done this is the best blog and advuce i,ve seen about wearing vintage i have difficulty finding original pueces to fit my over curvy shape so i tend to wear Retro vwith vintage accessorues . I do wear red lipstick mainly to events and dances but not everyday . Mught have a look at lipstain thank you

  16. Kim
    September 10, 2014 at 4:57 am (10 years ago)

    Great tips! I have another tip: when wearing original vintage: always take a small sewing-kit with you in your purse. It doesn’t take up much room but it can definitely be a lifesaver! I mostly wear reproduction dresses now, and I go for either rockabilly or sweet fifties girl and both styles make me feel amazing. You don’t have to limit yourself to one, just experiment with what you feel comfortable in and what looks good on you :)

  17. retromumma
    September 10, 2014 at 5:43 am (10 years ago)

    I live in and love vintage.
    I am 50 and I find that it is really tricky for me to look good in an ‘era I have lived and dressed up in’ already.. What I mean is that I love the 30s, 40s, 50s and I can still look good in a 60s Mod outfit – but when I put on a 70s maxi or a tied front poly dress or a drop waisted, big shoulder pads 80s number – I look old and dated….. just like I have had it in my wardrobe for 35+ years….
    So, I usually ‘wear vintage’ but with a couple of contemporary accessories or pieces – so that my look is more ‘retro eclectic’ rather than dated.

    • lollie
      September 10, 2014 at 10:12 am (10 years ago)

      My grandmother says “if you wore it the first time, don’t wear it when it comes back around.” I didn’t get it at 13 but at 33 & w the 80s in full effect I understand!

  18. Coralie
    September 10, 2014 at 6:19 am (10 years ago)

    What a great post :)
    Btw, I have also lipstick on my chin after eating ;)

  19. Sara Lawrence
    September 10, 2014 at 8:04 am (10 years ago)

    I am a disabled wheelchair user, I don’t dress vintage,but before I got I’ll my personal style was simple, smart, feminine, classy,I read this article, just out of interest and feel that I would like to congratulate you on a brilliant article, As I read on I could imagine myself following these tips closely and how it would look, I would loved to have seen some photos of how great you vintage dressers must look) Also your tips are so good and practical they could be used by anybody, no matter how they dress, I only had one firm rule, which I also passed on to my daughters, on aflirty night out, boobs or legs on show, not both

  20. Sara Lawrence
    September 10, 2014 at 8:07 am (10 years ago)

    Just to clarify, As there are photos, I mean of specific items like the flesh seamed stockings

  21. Patricia Lynn
    September 10, 2014 at 9:11 am (10 years ago)

    Wonderful and helpful post. I know I adjust my vintage look dependent upon the occasion. If I am at Art Deco Fest, I am in head to toe, all the “right” accessories, ’30s, because that is the theme of the event and other vintage aficionados can appreciate it. If I’m running errands on the weekend, I’ll do a ’40s or ’50s simple cotton dress or a vintage skirt with modern top and ballet flats. It allows me variety, practicality, comfort, and saves my treasured and more fragile ’30s items for occasions when they can shine as they were meant to. Anyway, who can afford $30 fully-fashioned seamed stockings every day? I can’t, even taking very good care of them. I think it is finding a balance.

    I also can’t agree more that if you are not comfortable in something, if it is poking you, slipping off your shoulder, so tight you’re afraid you’ll pop a seam, or in any way the focus of your attention, you won’t look elegant. You’ll look frazzled, stressed and fidgety.

    Wonderful advice, Lauren!

  22. Jackie Thayer
    September 10, 2014 at 11:21 am (10 years ago)

    Loved the article! If the clothes make your heart smile your whole body shines! I normally wear one or two pieces. .. but I don’t have a problem wearing a full on suit with jewelry to match. I agree it’s about fit, confidence and a splash of full on fun! Vintage style is fun…If it’s work…to me it starts to look forced :)

  23. Izora Zee Burns
    September 10, 2014 at 12:15 pm (10 years ago)

    For the homely (they think) girls: dressing in vintage makes you look So cute! There is a Swing Dance Group that comes up for our Jazz Fest & I thought that about several girls. In ordinary clothes, they just wouldn’t have that pizazz. Adding vintage glasses, especially Cat Eyes & red lipstick really polishes it off.

  24. Kathryn
    September 10, 2014 at 2:10 pm (10 years ago)

    While my “vintage” is 13th Century French, the majority of your points ring true. Thank you for posting this :)

  25. Maria DeBlassie
    September 10, 2014 at 3:47 pm (10 years ago)

    Absolutely wonderful advice! I love wearing vintage but have found that I have to wear it in a way that fits my natural style–especially with hair (too thick for victory rolls) and makeup (needs to be simple, no red lips for me!). Thanks for sharing this!

  26. Karen ~ Wall Flower Studio
    September 10, 2014 at 5:00 pm (10 years ago)

    Great blog & photos! Discovered your site through a friend who shared this post on Facebook. I’m a sucker for vintage clothes. : )

  27. Blake Canham-Bennett
    September 10, 2014 at 6:05 pm (10 years ago)

    Neat little article, even if only so many of these tips are appropriate for either gender (I would so very much love a similar article focused on men).
    Would certainly recommend this to women interested in vintage style though. Good luck with your Kickstarter, too!

    • Lauren
      September 10, 2014 at 6:54 pm (10 years ago)

      Great idea! I think I have someone in mind to write it :)
      Thanks very much!

      • Blake Canham-Bennett
        September 11, 2014 at 7:09 am (10 years ago)

        Ooh, I’m glad I decided to check back on this article, because I haven’t otherwise been notified of your reply (I would’ve figured that was the point of providing my email when leaving a reply, but perhaps not)!
        Is there a way in particular I can follow your blog (in so much as being notified of new posts) so that I can see such an article if it comes to fruition? I’ll be sure to check back for your reply!

        • Lauren
          September 11, 2014 at 10:14 am (10 years ago)

          Thanks! Yes, if you go to the upper left hand corner, there’s ways to subscribe- RSS for a blog reader if you use one, Facebook, Twitter, etc :)

          • Blake Canham-Bennett
            September 12, 2014 at 8:54 am (10 years ago)

            Thank you! Liked on Facebook and followed on Twitter. Plus now I’ve noticed when commenting that there’s an option to tick ‘notify me of new comments/posts via email’, so that helps too. So hopefully I’ll see any potential new posts regarding men’s vintage styles!

  28. AJ
    September 11, 2014 at 2:50 pm (10 years ago)

    Adore vintage! Thank you for the lovely article. And all the suggestions/feedback. Sadly for me, vintage clothes all to often don’t work as well with my bust. So, vintage look, style and patterns give me the looks I prefer. As I collect, refurbish, rescue and even sell vintage jewelry and other accessories & decor, I find myself getting deeper & deeper into vintage everything. Dishes to shoes, jewelry to furniture. Thank you again!

  29. Kate-Em
    September 12, 2014 at 8:54 am (10 years ago)

    This is a great post, you have covered all these points really well and I enjoyed the photos too.

  30. Natalie @ Quirky Vintage Blog
    November 3, 2014 at 1:42 am (10 years ago)

    Hi I’m new here. I found your blog (and this post) via Chronically Vintage’s Vintage Link Love post for October. Such a great post! I totally agree about the make-up. While I am a bit of a make-up addict and will often do a full face of make-up, I find that I usually only need a little bit of lippy to look “done”.

  31. Leigh Ray
    November 4, 2014 at 8:26 pm (10 years ago)

    I just love this post and your blog!! I’m finally embracing my love of all things vintage and incorporating it into my personal style and home. I’m looking to gradually make my life vintage. Do you have any advice on how I can slowly introduce vintage into my personal style and home? Thanks!!

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