
I know I always say that pants are hard, but lately, that applies to dresses too. Unless you want to wear one of these fun numbers.
Anyway, with so many dowdy dresses in stores right now, it can be hard to find a flattering style, but I’m going to demystify the process of dress shopping for you today. And we’ll start with a personal favorite of mine.
Anatomy of a Dress

This J. Crew Point Sur Collection dress, which I bought at Marshall’s for about $20, checks all the boxes for me! Besides being a flattering color, it is easy to care for (no wrinkles), light, breezy, and comfortable. Plus, it checks some key boxes for me:
- V-neckline
- Defined waist with blousey effect for tummy flattery
- Long but lightweight sleeves so I can wear them indoors and out
This dress was so perfect and such a rare find that I altered it from its slightly awkward midi length to my perfect Fashion Fit Formula length, and now it’s pretty much the perfect versatile dress.
And yes, it has pockets.
Let’s break down each of the five elements of a great dress: Neckline, Waistline, Length, Sleeves, and Details, one by one. (All of the dresses in this post/video are from Boden, and can be found in this catalog).
Using your current (or past) favorite dress, and a dress that you don’t love, analyze them for the following features:
The Neckline
The right neckline is key to flattery! A horizontal neckline can balance out a pear shaped body, while a vertical neckline can be very flattering on a proportional body, or a body type with broader shoulders.
Beyond that, the spot where your neckline hits (which you can get through Fashion Fit Formula) can be the key to lengthening your neck, balancing your body, and flattering you overall.
What’s your best neckline? Worst neckline?
Boat neck V-neck Scoop neck Square neck Crew neck
The Waistline
Another critical element, having the waistline at the right place can make you look slimmer, taller, and all the things. For example, on my proportional Style Dial Red body type, an empire style is super unflattering and makes me look pregnant, where it can be super flattering on a Style Dial Orange or Green (fuller hips and thighs) provided you don’t have a full bust.
Like I said, it’s important.
What’s your best waistline? Worst waistline?
Straight waist Empire waist (slight) Regular waist
Length
The right length is the one that makes you look longer and slimmer, and that’s where the Fashion Fit Formula can help. The other thing you need to think about is where the hem is hitting you on the leg. That hem is a detail that draws the eye, so make sure the dress ends at a flattering point on your leg.
What’s your best length? Worst length?
Knee Length Maxi Mini Midi
Sleeve Length
Sleeves can play a role in flattering a number of ways. Not only do they conceal/reveal an arm, depending on your preferences, but the end of a sleeve can also create a horizontal line that highlights/amplifies the bustline or a tummy area. Many women, after a certain age, prever an elbow length or three-quarter sleeve over the often challenging cap sleeve or short sleeve.
What’s your favorite sleeve length? Least favorite?
Sleeveless Short sleeve 3/4 sleeve Long sleeve
Details
Details can make or break an otherwise potentially flattering dresses. Ill-placed pockets, an oversized collar, a poorly positioned print, awkward ruffles… these all play a role in the flattery of a dress.
Which details have worked for you? And which have been dealbreakers?
Ruffles can be fun or unflattering Pockets can highlight problem areas An oversized collar may be unflattering to your face shape, or frame it beautifully Color is a key detail to pay attention to, and often the first thing we see Pattern, such as this horizontal stripe, can be a flattering detail, or not
3 Universally Flattering Dresses
Disclaimer: You might hate one of these dresses. Or find it super unflattering. But these 3 dress styles are the ones that I’ve found tend to flatter most women, most of the time. (All other details aside).
Shift dresses are generally easy to wear and flattering on many shapes Shirtdresses are flattering on many shapes. The fit and flare, especially one without a waist tie, works on many women.
Now I’d love to hear your thoughts! How do you feel about dresses, and which of these details will most help you choose the best style? Let me know in the comments!
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