Friday Five: The Hemline Edit
Not all dresses and skirts are created equal—here's how to find the shapes that flatter and function.
There are a lot of trends competing for your attention right now, but if there’s one thing I’ve learned after years of helping women build wardrobes they actually wear, it’s this: silhouette matters more than trends.
The right shape can make getting dressed easier, flatter your proportions, and instantly make your outfit feel intentional.
Today, I’m breaking down five dress and skirt silhouettes worth knowing—from timeless classics to one wildcard pick that deserves more attention.
Let’s get into it.
1. The A-Line Silhouette
If I could only recommend one universally flattering shape, the A-line would be at the top of the list.
Fitted through the waist and gently flaring away from the body, the A-line creates balance and movement without clinging. It’s feminine, timeless, and works in virtually every season.
Best For:
Pear-shaped bodies
Hourglass figures
Mid-size and curvy body types
Why It Works:
The flare skims over the hips while defining the waist, creating a balanced silhouette that feels effortless rather than restrictive.
Three Ways to Style It:
1. Casual Chic
Shoulder bag (borrow this one! Code JENANDREWS will get you your first month off free!)
Perfect for errands, brunch, or vacation sightseeing.
2. Elevated Everyday
An easy warm-weather uniform that always looks polished.
3. Date Night
The defined waist and movement of the skirt do all the work.
Favorite A Line skirts and dresses I love to shop:
This, this, this, this, this, this, this, this, this and this
2. The Column Silhouette
Minimalists, this one is for you.
A column silhouette follows the natural line of the body without excessive volume. Think sleek, elongated, and sophisticated.
Whether it’s a knit dress, slip dress, or straight skirt, this shape creates a clean vertical line that instantly feels modern.
Best For:
Rectangle body shapes
Tall frames
Athletic body types
Why It Works:
The uninterrupted vertical line creates length and elegance while allowing accessories and styling details to shine.
Three Ways to Style It:
1. Quiet Luxury
Simple and expensive-looking.
2. Layered Minimalist
Perfect for summer travel.
3. Evening Ready
Effortlessly sophisticated.
Column skirts/dresses I love to shop:
This, this, this, this, this, this, this and this
3. The Maxi Length
The maxi is having a major moment—and honestly, it never really left.
Flowing, comfortable, and surprisingly versatile, a great maxi dress or skirt can be styled for almost any occasion.
Best For:
Tall body types
Curvy figures
Plus-size women
Why It Works:
The longer line creates drama and elegance while offering comfort and coverage.
Three Ways to Style It:
1. Resort Ready
Vacation mode activated.
2. Weekend Casual
A practical outfit that still feels put together.
3. Elevated Evening
Perfect for summer dinners and events.
My favorite maxi skirts/dresses to shop:
This, this, this, this, this, this (JKB10), this, this, this, this, this and this
4. The Midi Length
The midi is the workhorse of the modern wardrobe.
Hitting somewhere between the knee and ankle, it offers polish, versatility, and endless styling possibilities.
Best For:
Petite women (when proportioned correctly)
Hourglass figures
Mid-size body types
Why It Works:
The midi creates elegance without feeling overly formal and transitions seamlessly from work to weekend.
Three Ways to Style It:
1. Office Appropriate
Professional without feeling stuffy.
2. Weekend Style
A formula that never fails.
3. Dinner Out
Simple, chic, and flattering.
Midi skirts/dresses I love to shop:
This, this, this, this, this, this, this and this
5. The Wildcard: The Slip Silhouette
If you’ve been avoiding slip dresses because they feel intimidating, hear me out.
The modern slip dress has evolved. Today’s versions come in satin, knit, bias-cut, and matte fabrics that are far more wearable than their 90s predecessors.
When styled correctly, they’re one of the most versatile pieces in your closet.
Best For:
Hourglass figures
Athletic builds
Petite frames
Why It Works:
The bias-cut fabric softly skims the body rather than squeezing it, creating an elegant and effortless shape.
Three Ways to Style It:
1. Everyday Cool
An easy entry point if slips feel intimidating.
2. Minimalist Chic
Simple and incredibly stylish.
3. Evening Glam
Proof that one dress can do it all.
Chic slip skirts/dresses I love to shop:
This, this, this, this, this, this, this and this
Final Thoughts
When shopping for dresses and skirts, focus less on what’s trending and more on which silhouettes make you feel your best.
A great silhouette works with your body—not against it.
The trendiest item in your closet won’t get worn if the shape isn’t right. But the right hemline? You’ll reach for it again and again.
Also, 5 new things I’m obsessed with this week:
1- Our new Ruggable rug: you guys if you don’t have a Ruggable rug, what are you even doing with your life? You can throw them in the wash, such great quality and the rug pad is attached! (We got the blue color way and I AM OBSESSED!) Love this one too!
2- My new one piece swimsuits: this and this one! It has sculpting technology and not too skimpy and so many color options! Love it! I also got this little wrap that also comes in a ton of colors for a little more coverage. I love this brand so much!
3- Skincare: I got another bottle of my “magic serum” that has the best consistency and have to have it year round. And then I got this cream and mask and have already used it so many times!
4- These sleep gummies have really helped with my sleep and don’t leave me feeling groggy like most do! My new go to! (Use my code JENNIFERANDREWS for 15% off!)
5- I’ve worn these or these jeans every day since I got them! Both soooo flattering!
Lastly….
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!
Love you guys, xoxo Jen
Some of the most wearable shapes of the season, styled right. So glad to be part of it, Jen!
Always love your recommendations, how detailed you are. Always great posts