Good morning everyone, today’s post is on styling a pair of tailored shorts for the cooler months. I adore wearing shorts even when the temperature drops. So with that in mind I thought I would show you I how I like to style a pair of tailored shorts for autumn/winter. Take a scroll down to see what items of clothing I have used to style my shorts. These are all items I already own and that were in my closet the only new purchase here is my bag!


/ SHORTS Similar / JUMPER Similar / BOOTS Similar / BAG / BELT / SUNGLASSES Similar


So I shall start off with my Reiss tailored shorts which are from last year. They come in this Ecru colour and I adore them as they always make my outfits look polished. Now as I love them so much I wanted to be able to wear them during the autumn winter months too. Of course I won’t have a problem wearing it all year round here in sunny Dubai. I wanted show you all that the shorts can be worn where the climate is much cooler. Just think of the shorts being like a mini skirt, but even better as I tend to find a pair of shorts to be much more practical than a mini skirt. What do you think?



The oversized jumper is one piece of clothing that is great to style with the tailored shorts. My jumper is from Zara and it gives me all the warmth I need, a bit too much for me at this moment. However I do know that for some of you this still might not be warm enough. So why not throw on a coat in either white or black and that should do the trick.



As for the shoes a pair of knee high boots is definitely the way to go. They will for sure cover up most of your legs leaving a tiny gap between the shorts and the boots. By all means you could also add some tights if you wanted some more added warmth. The boots that I am wearing are from Kurt Geiger and are a few years old now. I adore them so much that I have two pairs of them. I am very picky about my boots as most of them are too wide for me up top so when I do find that right pair, you know I am going to by a second one!



Next to give my outfit some shape and pull it together I added a belt. This is what makes the outfit look pulled together by cinching in my waist and giving it some shape. This tan waist belt is from H&M, at such an affordable price it sure does the job here. Finally finishing my look I opted for my The Attico leopard print bag and my white cat-eye sunglasses from Illesteva.


How would you style a pair of tailored shorts for autumn winter? Do let me know by leaving a comment below.

AD *This post includes affiliate links*


Shorts: REISS Similar

Jumper: ZARA Similar

Boots: KURT GEIGER Similar


Sunglasses: ILLESTEVA Similar

Belt: H&M




  1. November 11, 2020 / 10:42 am

    I absolutely love this outfit. I’d never think to put those shorts with boots like that but it looks great!

  2. November 11, 2020 / 8:05 pm

    Great outfit! Those style of shorts are dressy and paired with boots really make a statement.

  3. November 11, 2020 / 9:07 pm

    I love how you styled these white tailored shorts for colder weather. They look great paired with a jumper and boots.

  4. November 11, 2020 / 9:43 pm

    Accessories really make this look totally fierce and dope while it still seems so cosy! Totally my kind of style


  5. November 12, 2020 / 3:09 pm

    I love this styling, it looks incredible. I’m always freezing so I don’t think I could pull this off in winter but I’m definitely saving the inspiration for slightly warmer climates x


  6. November 12, 2020 / 3:27 pm

    I love how you’re wearing theses tailored shorts.
    Such a great idea.
    I especially love how you waisted this oversize sweater with the belt over you shorts. It looks amazing.

  7. November 12, 2020 / 6:32 pm

    Wow, you look absolutely amazing in your tailored shorts paired with those tall boots! I’m also loving the leopard purse! I’m sure I would need to wear tights underneath to combat the colder than Dubai temperatures during a Belgian Winter 🙂 xxx

  8. November 12, 2020 / 7:12 pm

    It;s so fun to style clothing items together that typically don’t go together like you did here – shorts with a long sleeved top or a dress with combat boots. This outfit is fabulous, Lovely!


  9. November 12, 2020 / 7:53 pm

    This shoes are beautiful 😊

  10. November 12, 2020 / 8:16 pm

    Such terrific styling ideas! I love pairing tailored shorts with tights and knee high boots.

  11. November 12, 2020 / 9:43 pm

    Oh yes I totally agree–shorts are so much more practical then a mini skirt. When I wear short skirts I wore cycling shorts or cut off tights underneath lol. I loved how you styled yours here with the belted over-sized sweater and knee high boots. Super chic as usual!

    Allie of

  12. November 12, 2020 / 11:24 pm

    I love the belted sweater with this look – it’s so chic. I would love to copy it, but I find that too bulky on me most of the time. The leopard bag is such a great pop of pattern, Lovely!

  13. November 13, 2020 / 5:50 am

    The shorts really do pair well with the boots. I never would have thought that would be a good look, but it totally works!

  14. November 14, 2020 / 6:05 pm

    Tailored shorts just look so smart and classic, don’t they? Love how you have styled your outfit. You look fabulous!

    Aimsy xoxo

  15. November 17, 2020 / 9:40 pm

    You look so chic, Lovely! I also like wearing tailored shorts in cooler months. 🙂 Your animal print bag really completes the look!

Leave a Reply

Your email address will not be published. Required fields are marked *

%d bloggers like this: