When a styling session takes an unexpected turn…

A few of my readers have asked about my process for putting outfits together. In this post, I’m sharing how I recently styled a new plaid blazer.

Whenever I buy a new piece (no matter how much I love it) I don’t remove the tags right away. First, I want to be sure that it will work cohesively with other pieces already in my wardrobe. And I want to be sure that it’s not too similar to something I already have.

My styling process isn’t always linear. In fact, it’s rarely linear, specially if I’m trying a new cut or silhouette. In this case, it’s a cropped blazer that I loved the minute I slipped it on in the dressing room. For the past several seasons, I’ve been trying to re-create the relaxed-plaid-blazer-with-jeans look I’ve been seeing everywhere on Instagram, Pinterest, etc. But oversized blazers just don’t work for me. So I thought maybe this more fitted, cropped version would be the “tweak” on the look that would make it come together.

Creating an outfit with a cropped plaid blazer starting with a flat lay.

Usually I start with an idea of the vibe I’m going for with an outfit, and play with a flat lay to see how the pieces I have in mind work together color and texture-wise. Here I was going for a neutral, slightly “tomboy” look with some feminine elements (bag & jewelry).

Outfit #1 – starting point

Susan B. wears a cropped plaid blazer, Saint Laurent LouLou puffer bag, a v-neck sweater vest, crop fray jeans and oxford shoes.
My sizes: blazer – Small, jeans – 28

It may have been “good on paper,” but on me I don’t think the overall effect stuck the landing. Not terrible, just “meh.” I could have added a colorful tee or more jewelry, but it would have been something different than the simple and neutral look I was going for.

Outfit #2 – heading in the right direction

I decided to switch things up with a wide leg jean and a more feminine shoe.

Susan B. wears a cropped plaid blazer, ribbed knit top, wide leg jeans, gold bangle & slingback shoes.
My sizes: blazer – Small, top – Medium, jeans – 28 (probably could’ve sized down to 27)

I like this better! The wide leg jeans feel more modern, and I like the clean lines of the shoes and bangle. The ribbed top adds some interest without being too focus-pulling or fighting visually with the blazer.

Outfit #3 – winner!

Then on a whim, I went in a very different direction…

Susan B. wears a cropped plaid blazer, v-neck silk tank, wide leg brown pants, gold sneakers.

And wouldn’t you know, I like this one the best! The relaxed trousers and sneakers deliver that whiff of insouciance I was going for. The metallic shoes add some texture/shine. (I forgot to put it back on for the photo, but the gold bangle from the second outfit works well here too.)

The wide leg trousers are linen from Eileen Fisher, and no longer available. Even though they’re a lighter fabric, the darker color gives them enough visual weight to work with the jacket. This trouser style from Madewell would probably work well too.

Now that I have a sense of the cuts and styles that work well with this plaid blazer, it will be much easier to create new outfits. Even if you rely on tried-and-true style formulas to make getting dressed easier, it’s good to experiment periodically with new combinations. Don’t be afraid to try something outside of your comfort zone or something that “shouldn’t” work. You may be surprised and find fabulous new ways to wear some of your favorite pieces.

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  1. Your blazer is a winner. The second outfit is my favorite, it’s crisp, versatile, and flattering on you. While oversized and cropped styles look nice on others they have never worked for me. I keep crossing my fingers for the resurgence of in the middle clothing. They did exist at one time.

  2. The third outfit looks fantastic, very stylish and up to date. The wider trouser leg with the cropped blazer looks balanced – but, I really like the tonal colours giving it a very chic air indeed.

  3. Susan; I too love the third look!!! The first two felt stiff/uncomfortable to me but the third look is perfect. As soon as I saw it my brain went “aahhhh.” Thank you for always sharing your inspirations with us.

  4. Thanks for the inspiration – I need to learn how to put my outfits together better. I also need to follow your example and not take tags off of clothes right away even if I think they’re a slam dunk (I am looking at the wide leg Rag and Bone jeans I bought that I am having a very hard time styling). All the best, Katie

  5. I like ALL the outfits, but I certainly see what you mean about the “wow” factor on the last option. (You’re much braver than me, trying new ways of styling.)

  6. Is the v-neck top in outfit #1 the same as the v-neck top in Outfit #3? I’m surprised that the v-neck seems to make a difference. The crew neck top seems a bit “stuffy”

  7. Thanks for walking through your process. I liked each outfit a little better too! Somehow I thought you just put things on and they always looked fantastic.

  8. Gorgeous! I like looks 2 and 3 and I love the cut of the blazer. I’m 5’ 4” and have always liked short jackets on me.

  9. Great post! Thank you for sharing the process and the options. Even though I’m taller at 5’6″ I struggle with the visual proportions of pairing a boxy jacket and wide leg pants. Seeing the different options shows why that look is more modern. Your creativity and style are an inspiration!

  10. Love #2 and #3 — the latter reminds me of wonderful Katherine Hepburn photos of her on a bike. I think wide-legged trousers were her signature style, and she was fabulous in them.

  11. Thank you for going through your process. I need a full size blazer but cropped looks good on you. I think the blouse in the final look nails it. If I could find it “not Cropped” I would buy it. I also think the darker colored pants really anchor the look. Dark navy jeans might also work.

  12. Susan, can you explain why you chose the top for look 3? I actually loved your look 2 top (my style is very classic ) so I’m interested why you changed it out (and why it does work better!) for look 3. Thanks.

    1. Hi Michelle, I think you’ve hit the nail on the head. #2 is a more classic look, and my style personality is Natural Gamine, so I need some playfulness in the mix. I think #2 is a great casual Classic look, though!

  13. I LOVE the first look on you!! Isn’t that funny, but you have to do what you like best of course. But I love that first look !!

  14. What a great post! I often go through this process of picking out an outfit and then adjusting it several times before I leave the house. I used to think of that as “frustrating,” but now I will think of it as “styling.” Thanks!

    1. Thanks, Susan! I try to work out some outfit ideas when I have time to experiment, then take photos for reference so I’m not scrambling on those days I need to get out the door early.

  15. How does someone tall (5’10”) pull off a cropped blazer outfit look without it just looking like the blazer is too short on me? Also any ideas on shorter but too short blazers for us tall ladies?!

    1. Hi Tamara, if you’re taller or long-waisted, I’d suggest a nice high-waisted pant (maybe even a pleated style?) and tucked top. Maybe even add a fun belt.

  16. I love the blazer. This is an excellent look on you. I’m about your height and usually can’t shop with Madewell because they carry very few petite sizes. May I ask if you hade to have the sleeve length tailored for you?

    1. Thanks, Laurie. I haven’t had the sleeves adjusted on this one, and will probably opt to just roll/cuff them as I have here. When there is a button cuff, a tailor will usually want to shorten a blazer from the shoulder, and that would make the plaid unmatched.

  17. Is it possible that finally, there is a style that looks better on us short people? I have seen the cropped blazers on tall models and my brain says “where is the rest of the blazer”? Seeing you in one just looks right! I guess it’s a matter of proportion.

    Are you planning on trying a boxy, cropped blouse? I see that they have become popular.

    1. Yes, it’s all about proportion, which can be tricky for all of us to get right, especially when trying a new silhouette. I’ve been wanting to try the cropped blouses, but haven’t yet seen one in a good color for me. Stay tuned…

  18. This is a great post and lesson in how to style something so it will work in your wardrobe. I like both looks 2 and 3. Thanks also for the tip to leave the tags on and do some trying on and imaging before adding it to the team (of clothes). You always look so put together, Susan.

  19. Amazing how much further down on your hips it sits compared to the tall models and how well it suits you as a result. Love #3 and also could see cord pants working too.

    1. Yes, I’m not only short (5’1″) but short waisted too, so I always have to take that into account when looking at images online, usually styled on a model who’s probably 5’9″ or so.

  20. Susan,
    Yesterday you commented that there is a red for every seasonal palette. I am a summer who can also wear more hot (aka “winter”) pinks. What color of cool red would suit my mostly summer palette? I love red and would like to add some to my wardrobe.
    I so appreciate your presentation of colors with seasonal palette labels. It really helps educate us about colors (like reds) that aren’t always in our list of preferred colors.

    1. Hi Julie, Summers usually do best with soft, pink-y reds. Think cherry red, strawberry, but not too bright and saturated.

  21. I live in Montana. It’s an understatement to say that the style here is EXTREMELY casual, so much so that it would be easy to garner a bit of resentment for having gone over the top with my wardrobe selections. That’s why I was so excited to stumble on your posts, Susan. They offer guidance on achieving just the right type of casual chic for this area and lifestyle.

    Like you, I am not fond of the oversized, slouchy style of blazer. Do you have any thoughts on what body types would be complimented by cropped blazers? Thank you in advance for any advice you may have.

    1. Hi Tammy, I hear you about not wanting to “overdress” for one’s region. I’ve seen women of all heights wear a cropped blazer. As far as body types go, it really depends on the cut of the blazer, the proportions of the whole outfit, and your own style personality and preferences. When we do a style analysis, we typically look at proportions (long-waisted, short-waisted, etc.) to get a sense of which jacket lengths will work best.

  22. It’s nice to see the way you try different options. Absolutely agree that the first outfit is fine, just nothing particularly exciting. I think that second looks is lovely; crisp and polished, without being stuffy or ‘trying too much’. The third one is fun; I could definitely see it for a weekend out and about, antiquing, lunching with friends, etc..

  23. I applaud you. You styled this perfect jacket really well. Love the last outfit you created. Very modern and laidback. I like the outfit with the wide jeans too and I agree on your “meh” on the first outfit. I have gone through a similar styling session with wide trousers as a starting point. It took quite some thinking before I got it right. The usual ways weren’t the right ones anymore. And when I tried a fitted jacket with normal, slightly fitted trousers, it looked dated. I think I am finally over skinny jeans. But, they served me well for at least 10 years.

  24. Thank you for this advice. I’m glad I am not the only petite woman who feels overwhelmed by the oversized blazer trend! Just this week I finally found a beautiful wool blazer, proportioned for my frame, at J Crew.

  25. Susan-
    I love those washable silk tanks from Quince (your top in #3), so affordable and I wear my fall colors in that line so often. Also love hearing/seeing your process and where you landed.

  26. Susan, you have certainly got me thinking about the plaid blazer I have had for quite some time. Longer style ( I’m 5’3”) but a nice shape that isn’t boxy. Not quite cool enough here but ready to style. I purchased the Everlane cashmere wool vest you highlighted a few months back ( gold) and I know that’s going to be a great way to to wear the blazer .
    I smiled seeing your rolling rack. I have one due to you. It comes in very handy when selecting clothes for my travels. It is still in the bedroom though, because I am slow putting washed and pressed clothes away from my recent trip to Milan and Venice. Then I will get going choosing clothes for a fall consignment drop off. It really must be returned to the garage then. Not in a convenient corner like yours!