Ask HOPE ROBERTSON | How to Wear Shorts
Hope,
I need to find some stylish shorts for this summer. Can you tell me some lengths and styles that would work for someone 5′ 5″ or shorter? Thanks for your help!
Blame it on my alabaster complexion, but I’ve always sworn by bermuda shorts when warmer weather starts. This 
summer, though, I’m so loving the wide variety of shorter shorts that I think I’m going to raise the hemline, even if it’s just by a few inches.
Wearing shorter shorts isn’t as daunting a task as you may think. While having a fear of showing off less-than-glorious gams is totally understandable, especially if your name’s not Gisele; wearing shorts with an inseam of 5 inches or shorter is actually quite simple.
My advice is this: If the shortest shorts you’ve ever worn are actually capris, then stick with bermuda shorts. If you love wearing bermudas but you want to wake up your wardrobe this summer, try a 5 inch inseam. And if your confidence 
permits, style shorts with a 3 inch inseam. (I find that a 2 inch inseam looks ill-fitted, even on someone with legs like a supermodel.)
I love the selection of shorts at J.Crew. These 5 inch shorts would look fabulous paired with a menswear-inspired button down and some colourful ballet flats. The inseam actually works to create the illusion of lengthier legs, and the fit is completely flattering.
Also flattering, — and spot-on for this summer! — are Lotta Stensson’s black linen sailor-cuffed shorts. Less about the 3 inch inseam, and more about the sweet sailor styling, these shorts would make a serious statement paired even with a simple white tank and gladiator sandals. I’m especially loving the gold-tone anchor buttons on the front! (And luxurious linen is a must-have to beat summer heat.)
If you’re looking for a bargain, prices can’t compare with Old Navy. I found these cuffed twill shorts, with a 3 1/2 inch inseam, on clearance for less than twenty dollars! Available in black, brown, or white — and still in every size — these shorts are the epitome of casual chic. The tonal topstitching and rolled cuff give them a real safari-like feel.
Let me know if you see anything you like!
J.Crew 5″ short heritage chino, $39.50, JCrew.com
Lotta Stensson black linen sailor cuffed shorts, $75, Bluefly.com
Old Navy low-rise cuffed twill shorts, $15, OldNavy.com
I bought the Old Navy cuffed shorts in chocolate and white w/ black pinstripes this weekend. They’re super comfortable and flattering, and they were on sale for only $10 each!
Oooh, nice! I love it when the store price beats the online price. How long is the inseam in those shorts?
Whatever your “report” said–they’re the same shorts.