Friday Five: The Five Things I'd Stop Wearing This Summer (And What I'd Wear Instead)
(And five recent Summer outfits I’ve worn)…
There are certain pieces that quietly date an outfit. They’re not necessarily “out” (I don’t love that word because style is personal), but they can make an outfit feel a little less intentional and a little more...2014 Pinterest board.
As someone who spent years dressing celebrities and now spends an embarrassing amount of time studying what chic women are actually wearing, I’ve noticed something: the women who always look polished aren’t necessarily wearing expensive clothes. They’re simply making smarter choices.
Often it’s the smallest swap that elevates an entire outfit.
So if your summer wardrobe could use a little refresh, here are the five pieces I’d retire—and exactly what I’d wear instead.
1. Instead of distressed cut-off shorts…wear a tailored Bermuda short.
I know. This one may ruffle a few feathers.
But those tiny denim cut-offs with the strings hanging down can instantly make an outfit feel less elevated, especially once you hit a certain age or simply want to look more polished.
This summer, the chicest women are reaching for longer, more tailored shorts that hit mid-thigh or just above the knee.
Think:
The extra fabric creates beautiful proportions and gives your outfit a sophistication that tiny cut-offs simply can’t.
Pair them with:
It’s the difference between “I threw something on” and “I have excellent taste.”
My favorite Bermuda shorts:
These, these, these, these, these and these
2. Instead of tight white jeans…go relaxed.
Can we all agree that white denim is hard enough without it also cutting off circulation?
A super-tight white jean tends to highlight every wrinkle and crease—and in the summer heat, it can feel a little too…eager.
A relaxed silhouette, on the other hand, feels modern and expensive.
Try:
A wide leg
Or simply size up.
I tell my styling clients this all the time: sometimes one size larger instantly makes an outfit look more intentional.
The best-dressed women rarely look squeezed into their clothes. They look comfortable, confident, and slightly undone in the best possible way.
My absolute favorite white denim:
These, these, these, these, these and these
3. Instead of cropped pants…choose full length.
This may be my most controversial opinion.
For years we were told cropped pants make you look taller.
I respectfully disagree.
A full-length trouser or jean creates one long uninterrupted line, which is actually far more elongating.
Even if you’re petite.
In fact, especially if you’re petite.
The trick is simple:
Hem them properly.
Let them skim the top of your shoe.
Wear a slightly higher rise.
The result is cleaner, sleeker, and infinitely more current.
Cropped pants can often visually cut the body in half, whereas full length creates that beautiful, effortless line we all want.
Full length trousers that make me happy:
These, these, these, these, these, these, these and These
4. Instead of asymmetrical hemlines…opt for cleaner lines.
Asymmetrical hems had a very long moment.
And while I will forever love a little bohemian energy (Stevie Nicks, if you’re reading this, you’re exempt from all rules), many asymmetrical dresses and skirts can now feel slightly dated.
This summer, cleaner lines are winning.
Look for:
Subtle details like lace trim, embroidery, or delicate scalloping
The elegance comes from simplicity.
A clean hemline gives the eye a place to rest, and the entire outfit feels more modern and refined.
My favorite skirts:
This, this, this, this, this, this, this, this, this and this
5. Instead of a cork wedge…try a sleeker shoe.
The cork wedge had a glorious run.
But if you’re trying to elevate your wardrobe, consider retiring it for something that feels a bit more current.
Try:
These styles instantly make an outfit feel lighter and more sophisticated.
And here’s the secret: modern style often comes down to subtraction.
Less platform.
Less hardware.
Less fuss.
The chicest outfits right now have a quiet confidence to them.
My favorite low heel sandals:
These, these, these, these, these, these, these and these
Now for 5 recent outfits I wore and loved:
Top, trousers, bag (alternative), sandals and sunnies (own and love this similar option too)
Tee, knit, trousers, sandals, bag (alternative) and sunnies
Trench (alternative), tee, trousers, bag, sunnies, sandals
Tee (love this, this and this too), trousers (alternative and here too), bag (love this too) and sandals (just ordered this leather version; obsessed!)
Friendly reminder….
You can still book a personal Styling Zoom session with me at the very reduced rate of $200. My normal rate is $350. You can book 2 sessions for $350, three sessions for $550 and four sessions for $750 and if you purchase four sessions, you will get a free copy of my new style e-book as well.
Email me at jenknowsbesblog@gmail.com! These slots are going quickly!
If you want to download my new style ebook, you can do that here:
The JKB Outfit Formula Handbook
You can also download my other ebooks here:
The Only Style Book You’ll Ever Need
Minimal Chic: The Art of Dressing for your body type and lifestyle
Also, join my “JKB Edit” broadcast channel I just started here on IG for daily favorites and you can ask me questions over there as well!
Follow me and join my circle on ShopMy as well! I update my shopping links there daily!
And I update this regularly: The Best Spring/Summer shopping guide!
I also curated THE BEST Zara shopping selects here that give expensive minus the sticker shock here! (I updated this today!)
You can find my capsule wardrobe favorites here by category as well!
Love you guys, xoxo Jen











oooh i adore that black dress with the sunnies!!
I’ve been looking for a white mule heel but I’m struggling because I have very narrow feet and they just slip through these heels. Are they any you can recommend that are under 3” and good for narrow feet? 🤩