How to wear Jeans with a special top – the ultimate inspiration guide

by Sylvia

How to wear jeans with a special top |

Welcome to the first detailed exploration of casual style over 40 in the 40+Style Casual Challenge. This is week one and today we will discuss casual outfit formula #1: Jeans with a top.

As you can see that is exactly what I’m wearing although I have added a hat as well to make this look a bit more funky and finally join Judith for hat attack.


If you like to see all my suggested casual outfit formulas you can see them all there.

Casual outfit formula 1 - jeans with a special top |

Our first exploration of casual style begins with the good old jeans plus a special top. This can be blue jeans but can also be jeans in any other color. Bright colors are still popular as are white and colorful options.

What makes this outfit formula so great is that it’s very easy to wear, very comfortable and that with a bit of effort it looks effortlessly stylish.

You can easily make your outfit more or less casual by adding the right shoes and accessories.

The 40+ style stars of today have done exactly that and have turned this simple outfit formula into sassy casual chic outfits.

My outfit

The jeans I’m wearing today are the CORSET DENIM™ Marty Slim Bootcut jeans from IT collective which were sent to me for review. It’s a mild bootleg cut which is one of my preferred jeans styles. I like my jeans dark, so it is not too casual and these ones have a beautiful color.  Although some of you want your bootleg jeans really tight, I’m preferring mine a bit loser although I ordered my size according to the specifications on the site. These are size 29 and they are a comfortable fit. The length is perfect for flats for my height 5’7”). I love the fit and if you want to see a bit more on that, you can check some photos on my Facebook Page.

The jeans are paired with a new color blocked top from local label In Good Company. The designers of this new label used to be responsible for my beloved (now discontinued) brand Alldressedup and they are getting better with each collection. More of them coming up in later articles…

What I like about this outfit is that it is casual yet chic. Comfortable yet hip. All that the jeans needed is just a special top! I even kept the jewelry very minimal.

Corset jeans with a special top and hat |

Another of my go-to outfits is white jeans with a blouse. This is a combination I recently wore that I felt very happy in.

These jeans are from NYDJ (similar from NYDJ).

White NYDJ with a lila button down shirt |

Now, let’s have a look at your ideas!

boyfriend jeans with blue green striped top |

Alice (Happiness at Midlife) is looking great in boyfriend jeans. Notice how her accessories make this outfit really chic: the pointy shoes, the earrings, the handbag and watch!

Blue jeans with an animal print top from Covered Perfectly |

Lorraine is wearing her dark jeans with an animal print top from Covered Perfectly. She uses the same trick as Alice and adds more chic to her look with accessories. Below are four more great jeans + special top outfits from Lorraine.

Blue jeans with a printed t-shirt as worn by Lorraine | Blue jeans with a special top - Lorraine |

Paisley Top over distressed Jeans and Mary Janes - Daenel|

Looking bohemian chic with boyfriend jeans and printed tops - Daenel |

I’m loving the arty and colorful interpretations of Daenel (Living Outside the Stacks) whose looks exude a more arty and bohemian vibe. Great casual looks that are fun, playful and chic!

Blue jeans with blouse and sneakers - Laura |

Laura (Buckle Button Zip) is looking very chic in jeans with a shirt layered over a t-shirt. She opted instead to make her look more casual by rolling up her jeans and adding oxfords. Great for casual days!

Wearing jeans with special tops | Ana  | Looking casual chic in blue jeans with a special top - Ana |

Some women just look so good in jeans (or know how to wear them well) and Ana (Mrs American Made) is certainly one of those ladies. Four great looks from her!

Sporty in blue jeans on a bike |

The Wardrobe Mistress tells us all to do something active every day! She wears her go-to Mossimo Supply Co. jeans from Target, striped T-Shirt, bicycle print scarf from Charming Charlie’s, knock-off Tom’s from Rite-Aid, studded belt buckled at the side, and of course, a DK bicycle helmet. Looking very chic on her bike indeed!

 Looking very hip with blue skinnies and red pumps | Trina |

Trina (Teatime with Trina) is absolutely rocking her skinny jeans with these red pumps. So fun to pair these with her flowery blouse. It really increases the HIP factor!

Casual outfit formula 1 collages

Casual outfit formula 1: blue jeans with a special lace top |

Loving this elegant outfit from Sue (Polyvore profile) who combines jeans with a lace top.

jeans with sunflowers and fringe bag |

Finally Kay (Polyvore profile) adds a beautiful sunflower top to the jeans with a currently very hip fringed bag.

In short here is how you can make your simple jeans & special top outfit look stylish and hip!

  • Instead of a plain t-shirt, choose something with a print or a drape.
  • Jazz up your outfit with heels, pumps or a funky flat shoe.
  • Play with accessories to turn up the chic factor.
  • Roll up your jeans and add sneakers for a very laid-back casual look.
  • Play with accessories like a hat to make your outfit more funky.
  • Play with silhouette and see how different your outfit looks with different tops. Do you look better by tucking in your top, wearing it with a belt or losely draped over your jeans? Perhaps you can wear some tops different ways?
  • When tucking in your top consider adding a belt.

Are you ready for mini challenge number 2?

Casual outfit formula 2 is jeans + top + jacket or cardigan. Check here for more details.

There are a 2 ways you can join in:

  1. Photograph yourself in a look that follows formula 2 and send the photo(s) to me at sylvia [at] Make sure your photo is of good quality. You can send as many photos as you like, but they all need to follow the casual outfit formula 2, so this time you are adding a jacket into the mix. Feel free to use any kind of jeans (white, blue jeans, colored, prints) and / or
  2. Create a collage just like Sue and Kay did above in Polyvore. It’s free to sign up and create collages and you can post the link to your collage in the comments of this article or send it to me through email.

Please make sure your entry is in by Saturday 10 May.

I hope many of you will join in this fun dressing challenge and exercize your creative muscles with your dressing!

By the way, I have decided to add a contest element to the casual style challenge as well: the 40+ Casual Style Challenge Contest! All you need to do to enter is start pinning your favorite casual outfits that you spot on this site or around the net. Check this article for more details and to sign up!

For more 40+style inspiration you can also visit visible Monday.

I hope you enjoyed all this glorious casual inspiration? Do you wear this casual outfit formula often? Which of the above is your favorite outfit?


1 kay kerns

Casual Outfit Formula 2 Jeans, top, and a jacket or cardigan

2 Sylvia

Thanks for your submission Kay!

3 Patti

GREAT outfits here, Sylvia. Jeans with a special top is one of my favorite looks. Thanks for sharing with Visible Monday!

4 kay kerns
5 Belen de bellepoque
6 Alyssa W.

I think your hat makes it so “you”! I am the queen of jeans and a special top…working at Gap makes me well versed in denim, and my addiction to printed tops seals the deal! Lol


7 Sylvia

I hope you join the next mini challenge Alyssa!

8 It's Robyn

Jeans and a blouse (aka “special top”) and a mid heel wedge is my go to everyday outfit. My lifestyle is casual but I like to feel dressed up too. This outfit fills both needs. Robyn

9 Sylvia

Yes that is what I prefer to. And these are certainly easy to throw on outfits!

10 Trina

Sylvia, your color block tee (blouse) is to die for. This cute little tee took your jeans to a whole new level, and the panama hat was the perfect accessory. I know I already commented on your white jeans on Facebook, but you look fabulous in this outfit.
Thank you for including me in your challenge, so fun to see all the different ways to dress up some jeans.

11 Sylvia

Thanks so much for joining in Trina. Your outfit was fabulous too!

12 Alice - Happiness at Mid Life

Love how the hat form you first outfit really makes the outfit. And those jeans look so relaxed on you. Thank you for hosting this challenge.


13 Sylvia

Yes, they are comfortable AND look good. That is all I want from jeans.

14 Aileen

Great ideas and lovely photos of all the fabulous ladies. Thanks Sylvia, and Lorraine you are looking amazing.

15 Lorraine

You are very kind Aileen but I’m wondering whether to ditch the stripy top? I’m also going to sack the photographer who wouldn’t read Denton’s tips and made me squint in the bright sun!

16 Aileen Wrennall

It might just be the angle of the photo of the stripy top you don’t like, or the black/dark blue & white contrast which isn’t the best for us blondes. I am constantly wearing colours I shouldn’t, being fair skinned and light haired and when I see you in your beautiful turquoises, blues and pinks it reminds me I should be choosing those colours too.
I don’t know about you, but black and white is the worst combination ever on me and there are loads of b & w dresses in the shops right now.
By the way, your hair is to die for; I love it.

17 Lorraine

Aileen, I know, but I have loved navy and white/cream since I was a child and I am always drawn to it (see my Pinterest board!). I know high contrast isn’t so good but every year they trot out the nautical look and I get sucked in!
However, it’s not that but the cowl neck I am not sure about. I don’t need extra fabric near my bust! PS Just bought some bright pink jeans and was very tempted by some floral trousers!

18 Aileen Wrennall

The floral trousers would be great for you Lorraine, go on treat yourself.

19 Sylvia

Why ditch that top? It looks good and will be a great layering top as well…. At least you have a willing photographer Lorraine…

20 Lorraine

You are right Sylvia. I will try it with some other things. As for the willing photographer, he is in Saudi at the moment but I have printed out Denton’s advice and left it on his pillow! LOL!

21 Sylvia

haha, your husband is a keen photographer. I’m sure he will learn!

22 Lorraine

Yes, he is keen, but he doesn’t like to read instructions (of any kind!)…

23 Greetje

No man will ever read instructions….

24 Lorraine

Ah! I’m strangely comforted by that fact!

25 Beata

Great photos:) beautiful ladies:) Sylwia you look absolutely beautiful 🙂 I relly like the first outfit 🙂
Have a lovely Monday hugs Beata

26 Sylvia

Thanks Beata!

27 Lana

What a fun challenge – all of the outfits look great! Since I work from home, this formula is my uniform most days. I think my favorite was Laura from Buckle Button Zip – I love blue. Can’t wait to see more!

28 Sylvia

Next week there is another mini dressing challenge (see details in this article). I hope you join!

29 The Style Crone

Sylvia, I was so excited to see you and your hat pop up on Hat Attack. Casual and hip are the perfect words to describe your outfit. Your wear your hat with great confidence and I enjoyed viewing the bloggers who contributed to your challenge. Thank you for sharing with Hat Attack!

30 Sylvia

Haha I finally made it even though it’s my old trusty hat. Question: what do you do when your husband does not like hats and will always make a point of saying something about that?

31 Lorraine

If you are getting positive comments from other sources then don’t worry about your husband! And tell him to keep his comments to himself!

32 Sylvia

Yes but displeasing your husband a lot stylewise (I really want to wear MORE hats)… I’m not sure if that is a good idea…

33 Lorraine

To be honest, I just tried on some floral pants that fit me beautifully but I could see Nick wrinkling his nose up in my mind so I put them back – so don’t take advice from me!

34 The Style Crone

That’s a hard one Sylvia. Does he dislike all hats? Would he be willing to try wearing a hat?

35 Sylvia

Yes! And no he would not. You know what Judith? I think we still need to make that trip down to Colorado one day so he can actually see how glorious you look wearing hats! I mentioned that I want to wear more hats as I get older (also because my hair is not getting any better and I love how hats cover up a bad hair day!) He did not like the idea. On the other hand my hairdresser DID like my hat today (wore it again with another outfit). Yay!

36 The Style Crone

Yes Sylvia. Would love for you to visit Colorado. We could tour the hat room!

37 Lorraine

I think you have to ask him WHY he doesn’t like you wearing hats. Is it because:
* people look at you
* he doesn’t think they suit you
* he wouldn’t wear one himself?
Alternatively you just have to wear them when he’s not around!

38 Sylvia

He does not think they suit me (and many others for that matter). Don’t worry Lorraine. I will keep wearing them although I’m still looking out for better ones. They are not easy to find here as I need summer hats and don’t want (too many) beach hats!

39 Ana from Mrs. American Made

These are such fun, Sylvia. I always look forward to your challenges, not only considering what to submit, but to see the many lovely interpretations by everyone else. Thank you for hosting and for sharing your great outfits, of course. That color block top is so perfect – casual yet dressy. : )

40 Sylvia

Thanks Ana. Yes casual yet dressy. Just the way I like it! Thank you so much for taking part. Looking great as usual!

41 Lorraine

Thanks for including me, Sylvia, but I have just realised that I am the only one to be featured who doesn’t have their own style blog.
I am just an ordinary woman trying to learn about style so I feel at a disadvantage here!
I WILL carry on with the challenge but I really want to be featured with women who are like me.

42 Sylvia

Yes you are Lorraine and you should be PROUD. Believe me there a lot of non-bloggers reading these articles and getting inspiration from it. You inspire them just as much (or even more) than us bloggers.

I try hard to involve the non-blogging readers but most of them prefer to sit back and enjoy the articles and photos. To that end I also setup the Casual Style Challenge contest to get more women involved. That is easier as it just involves pinning. Not sure I will succeed though. Why not invite your friends? I will continue to invite everyone to join in too.

43 Lorraine

When you put it like that…….it’s just that I can’t compete with Mrs America and her long legs!

44 Sylvia

Her legs look proportionally tall. She is actually not very tall at all.

45 Greetje

Oh goodie goodie, all my favourites joined.
Sylvia: love your new top and jeans. Love the hat with it. Wear it when your husband is not around.
Alice already knows I totallt love this outfit of her.
Lorraine, what a pleasant surprise to see you in so many good casual outfits. Did you change every time into something new? As the sun and the leaves in four pictures seem to be the same. If that is so, be thankful to Nick.. the patient man.
Daenel is a new kid on the block for me. Love how she loves colour and especially love her kimono. I always love kimonos.
Laura is cool in these blues. Looking very good. Is it coincidence or art that she has this blue painting behind her?
Ana always looks great. Haven’t seen her making any faux pas yet. And these combinations are all beautiful. I especially like the top with the red stripes (something I will never try) and the cream sleeveless top.
The wardrobe mistress is wearing the colours of the Dutch flag. Yeah. Simple but effective.
And Trina did it again: looking so good. Trina I am a fan of this combination: love the skinnies, the shoes, the top, the necklace. Great job.
I am sure to join in the next challenge with a jacket.

46 Lorraine

Thanks Greetje. Yes, I have to make the most of him when I have his attention! It will be good to see you in the challenge, even if you are also a style blogger!

47 Jan Graham-McMillen

What a great group of women you’ve chosen to represent! We all live in our jeans and special tops … I’m always looking for ways to wear them, and they are underrepresented on my blog, in spite of the fact that I wear them so often. It’s that time of year here where pretty summery tops can take center stage, so I ought to take advantage of the inspiration here! Thanks, Sylvia.

48 julie @bohomumma

I love your top – it looks amazing – really stylish with the jeans. Fabulous collection of lovely ladies looking stylish

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