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*2025* What to wear with mary janes? 18 refreshing ideas!

*2025* What to wear with mary janes? 18 refreshing ideas!

Fashion comes and goes, but Mary Janes is here to stay. It’s such a classic and timeless piece.

The most underrated thing about Mary Jane is – it’s truly versatile!

WHAT TO wear mary janes
Source: Pinterest

From a modern high street look to retro vibes, this statement piece got you all covered.

So, ladies, it’s time to wear your Mary Jane to create a wide range of styles! Here are the 18 inspirations if you wonder what to wear with Mary Janes!

Enjoy!

1. WEAR A PLEATED DRESS WITH MARY JANE

Let’s start with the classic combination first – the Mary Janes and the pleated dress.

WHAT TO WEAR WITH MARY JANES?
Source: Fahsiongum.com ,2,3

Can we all agree they just look so perfect together?

If you want a youthful schoolgirl look, all you need to do is add a pair of plain round-toe Mary Jane flats with the checked pleated skirt.

Of course, you can wear a ruffle of white socks to make the shoes pop up!

pleated skirt mary janes outfit
Source: Whowhatwear

As for me, 25 years old, I prefer a more sophisticated look so I will always look for the knee-length satin pleated dress and pointed Mary Janes heels.

With a cowl neck or turtleneck top, this is how to look expensive without wearing any designer brands!

It’s always flattering to see the pleats dance in the breeze, and I will always pair a belt with this look for instant glamour!

Mary Jane Charles & Keith
Studded Crossover-Strap Mary Jane Flats – Charles & Keith

I hope I’ve convinced you that wearing a pleated dress is not only for teenage girls.

With your own pairing, you can definitely give your skirt your own character!

Trust me, there’s definitely NOT ENOUGH content for vintage fashion these days

If you are the retro girlies or Mary Jane lovers, there’s one thing for sure – you have impeccable taste.

If you find this recommendation useful – please kindly share and pin some of the shoes so more vintage girls like you can enjoy the info!

2. WEAR MARY JANES FOR A FORMAL LOOK

Another way to wear Mary Jane is to style it with workwear.

WHAT TO WEAR WITH MARY JANES?
Source: Glamradar.com

In the past, I always wore high heels for work but let’s be honest, it’s not the comfiest shoes during the weekdays.

Ever since I incorporated the pointed-toe Mary Jane pumps and heels into formal dressing, I just realized these types of shoes can add a dash of elegance and balance the formalness of the outfit.

Mary Janes formal outfit
Source: Pinterest

So now, whenever I wear something “aggressive” (in my own definition) like a full suit, I will always wear Mary Jane to make the outfit look more approachable!

3. DRESS DOWN YOUR MARY JANES WITH JEANS

If you want to dress down your Mary Janes, denim and a T-shirt are a no-brainer.

WHAT TO WEAR WITH MARY JANES?
Source: 1,2,3

Also, you can always opt for kitten heels, chunky heels, and flats for casual days.

If you are a petite girl like me and you wonder how to wear flats without looking short, embrace nude-colored flats.

By that, your legs and shoes are integrated visually and that makes the legs elongate more.

Plus, I will always opt for skinny jeans when I wear flats, showing the curves, just makes me feel more put together.

jeans Mary Janes outfit
Source: Pinterest

As for the flared jeans, they are truly flattering but always remember to show the ankle area as that can contour your body proportion visually!

But seriously, pairing Mary Jane flats with a T-shirt and denim is such a refreshing style, that just naturally makes you stand out from the sneaker crowd!

4. EMBRACE MARY JANES IN AN ELEGANT STYLE

When it comes to outerwear like the trench coat, pea coat, and polish cape coat, they all serve as a great pair with the lovely Mary Janes.

WHAT TO WEAR WITH MARY JANES?
Source: 1,2

With fabric like velvet and faux leather, Mary Jane is perfect for autumn and winter outfits.

With a lovely beret, you can effortlessly complete an British elegant look.

SOCKS MARY JANES OUTFIT
Source: Pinterest

My all-time favorite is wearing the elegant cape coat with the sheer black stocking and a pair of dark red velvet Mary Janes – simple yet classic!

5. WEAR SOCKS WITH HEELS

So here’s the all-time debate: Wear socks with Mary Janes or not?

WHAT TO WEAR WITH MARY JANES?
Source: 1,2,3

My answer is … why not?

I know it can feel a bit overwhelming when you first try it, but please don’t limit yourselves!

what to wear Mary Janes white thighs
Source: Closs fashion

Sock pairing is really fun to do and you can even save yourself some good money!

Why? Because with the same pair of shoes, you can literally get 5 different looks when you wear different styles of socks!

Despite the vintage look, you can also try sheer socks and fishnet tights for an edgy stylish look.

If you are interested in how to wear socks with Mary Janes without looking awkward, make sure you read these 7 tips!

I am sure you will find the last tip practical!

6. STYLE CHUNKY MARY JANE WITH BAGGY CLOTHING

If you prefer dressing oversized, wearing baggy outfits with the Mary Jane is the no-fail way.

WHAT TO WEAR WITH MARY JANES?
Source: 1,2

These days, the Dr. Martin Mary Jane is such a hit and I just can’t help but buy one too.

But here’s the question: How do I style it?

Mary Jane baggy outfit
Source: Pinterest

As Dr. Martin Mary Jane is quite chunky with the round toe, if styling something too light for the upper body, that can look slightly imbalanced.

So, I do think wearing something slightly oversized can be a nice option here as it can complement the voluminous shoes.

CHUNKY MARY JANE SWEATER DRESS
Source: Pinterest

To keep it simple, I will wear tone-on-tone outfits so my body won’t look dragged down by the shoes.

I may also wear a high bun instead of letting all my hair down for a more put-together look.

7. OPT FOR POINTED-TOE MARY JANE FOR A MORE POLISHED LOOK

Some ladies avoid wearing Mary Jane shoes as they don’t think the round-toe design fits them.

WHAT TO WEAR WITH MARY JANES?
Source: 1,2,3

Indeed, if you don’t have long and slim legs, a round toe can make your legs look visually thicker.

However, Mary Jane nowadays presents in more casual forms like the pointed toe and even the stylish square-toe block heels!

These designs can all elongate our legs and incorporate well with our outfits.

Mary Jane pointy heels
Source: Pinterest

It mildly annoys me that wearing Mary Jane will make you look like a Grandma. I mean, seriously? We all know that is not true.

Try out different types of Mary Janes and I am sure you will be surprised by how chic and sleek it is!

HERE ARE SOME TRENDY PICKS:

mary jane shoes

Shop River Island!


If you are reading till this point, I’m sure you are the fashion girlies. If yes, check out my newly set-up (Like literally this June) insta @hannahnfashion for more <3 See you there pretty ladies!

And guess what, if a guy ever asks you “what you bring to the table”, show him this reel lol

FINAL THOUGHTS:

So ladies, here are the 18 ways when you wonder what to wear with Mary Janes! Let’s have a recap first.

  • Wear the pleated dress with Mary Janes
  • Wear Mary Janes for a formal look
  • Dress down your Mary Janes with jeans
  • Embrace Mary Janes in an elegant style
  • Wear socks with heels for a wide range of looks
  • Style chunky Mary Janes with baggy clothing
  • Opt for pointed-toe Mary Jane for a more polished look

See! Mary Jane is not that hard to style at all!

Pairing with different tops and bottoms can easily be dressed up or down your outfits and the combination can basically be endless!

I used to think Mary Janes were for the school girls only but these days, I realize they can look truly feminine and classy as well!

With a ribbon silk blouse and pencil skirt, a pointed velvet red Mary Janes just elevated my whole look in such an effortlessly chic way.

So please ladies, get creative with your Mary Janes and create your own signature look!

If you are looking for more Mary Jane styling tips, feel free to check out the articles below. See you there loves!

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