Sneaker + Skirt = Sneakirt

When: On the last day of Spring, with lots of places to be around town, such as pilates class and shopping.

So I have to ask the question, would you wear sneakers with a skirt, or do you think it's just horrifying to even consider the thought?  I have seen the 1980's sneaker/skirt (Sneakirt) combo and it wasn't pretty then, however now I believe there may be some room for this trend if done correctly.

Number one: No socks please, we don't all need flashbacks from the 1980's & Working Girl.
Number two: The level of shoe detail should match the level of the outfit.  See above.
Number three: Color, color, color & pattern.  Use them to your advantage with your outfit.
Number four: High tops are not great for elongating the legs, a shorter skirt level is necessary.
Number five: Look for almond toe or semi pointed for an elongation of the leg.

This said, try things out.  Wear what you feel comfortable in.  My sister wore her Dr. Martens with EVERYTHING and you to can make it work if you own it.  It's the attitude that counts.

Sneakers: Converse by Jack Percell Helen Sequin Ox, similar via Nordstrom Rack $55/$125
Leather Skirt: Hinge Leather Panel Peplum Skirt via NR, $54/$150 expensive, reasonable
Top: J. Crew V-Neck Shell $25/$40 on sale now with an extra 40% off
Cardigan: Nic & Zoe via NR $20/$144
Handbag: Milly Victoria via NR $135/$435
Tote: Kate Spade via Ebay, $60