How to Style Dressy Shorts #FashionFriday

how to wear dressy shorts

A friend and blog reader wrote in and asked for ideas for styling and accessorizing her new black shorts. She bought them for date nights as an alternative to a skirt or dress.

For the past two seasons, I have very cautiously dipped my big toe into the dressy shorts trend, and once I get over my initial feelings of self-consciousness, I find that I really enjoy wearing them! I have a white pair and a coral pair, and I hope to add a black pair this summer.

If you’re feeling unsure, my best advice is to try out the new look when you’re going somewhere that you don’t know anyone. I often try out a new look at blogging conferences or when on vacation. I figure, no one really knows me, who cares? Once I get comfortable with the idea, I don’t feel so strange wearing them in my normal life. That is definitely how I got used to wearing dressy shorts.

Here are my best tips for styling dressy shorts.

How to Style Dressy Shorts

1. Start with the shoes.

Decide what shoes you want to wear. Are you going to lunch with girlfriends or out at night with your honey? For a daytime lunch, a flat sandal can be very cute. For evening, a wedge sandal works beautifully. You can totally go for a stiletto if you are comfortable going there, but that is a bit much for my suburban life. I have a couple pairs of wedge sandals that are very comfortable, and it’s nice to have a few options.

2. Go with a simple top or blouse.

You can tuck or untuck, but you want to keep it fairly neat. This isn’t the time to look sloppy. You don’t want a top that is too long, or it will throw off the proportions. You don’t really want a voluminous top, but neither do you want it skin tight. Since the shorts are a bit of a statement in and of themselves, I tend to keep my tops subdued and modest.

3. Accessorize!

This is the time to break out a statement necklace or a pair of big, dangly earrings (but not both, pretty please!!) As you can see from the photos above, I tend to use this opportunity to bring out a statement necklace. And I love carrying a bold handbag as well. This is a great time to pimp my NEW BIZ. If you’ll indulge me in a bit of shameless self-promotion, I’m now an independent consultant for Stella & Dot! You can shop online at anytime through my online shop, and I hope you will “like” my Facebook page where I am sharing the latest promotions as well as fun styling tips and videos: Jo-Lynne Shane, Independent Consultant for Stella & Dot.

4. Shave and lotion, girls.

This should go without saying, but… you never can be too sure. Also, a little self-tanner never hurts either.

5. Pay attention to fit.

The length of your shorts depend largely on your figure type and your proportions. If you are petite, you can get away with a shorter short. I’m not that tall, but I know that I’m leggy, so I try not to go too-too short, but I also don’t care for Bermuda shorts on myself. They make me feel dumpy.

On the other hand, if you are self-conscious about your legs, try wearing shorts that come just above the knee. But make sure they’re not too baggy or too tight. In fact, that goes for EVERY length of short.

You don’t want the shorts to be too baggy, but you DEFINITELY do not want them to be too tight. Just as with pants, you want them to fall straight down from your hips. Shorts that flare can make you look wider than you are. You may have to try a few different brands and styles to find shorts that work well for your body type.

Here are a few outfits I put together on Polyvore. These are VERY old, so I don’t have links, but you can get the idea.

Shorts with a Blazer and Pumps

shorts with a blazer

Monochromatic Shorts Outfit with Flats

Monochromatic Shorts Outfit

Shorts with a Blouse and Wedge Sandals

Shorts with a blouse and heels

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14 Responses

  1. Love dressier shorts, but I struggle with that perfect length. I find if they are shorter ( like 3 inches) I size up to get them a bit looser so they don’t look like hot pants. A 5 inch length is perfect for me but not always easy to find.

  2. Great outfit ideas. The third one is my favorite, really cute picks.

  3. Dressy shorts outfits are my favorite for summer date nights! I really love all of these ideas but especially that last one. I have all of the pieces in my closet already! Hope you have a wonderful Mother’s Day!

  4. Dressy shorts are such a great alternative to wearing a skirt! I don’t wear them often enough. Love the looks you put together! My favorite is the mint and coral outfit! Hope you have a wonderful Mothers Day!


  5. So much great inspiration here. I’m a huge fan of shorts…for dressing up or dressing down. 🙂 I agree with Jane that finding the right inseam and cut is a huge part of getting the right look. When I find a pair I love, I tend to buy them in every color. And backups of black and white. 🙂
    Gina — On the Daily Express

  6. All great looks, but my favorite is the Shorts with a Blazer and Pumps. Although, I don’t have the best legs, I would totally rock that look.

  7. I love dressing up shorts but it requires toned legs for sure and knowing what length compliments your figure. I’ve found that I can’t go any higher than 5 inches. Hitting the gym as much as possible these days! You look adorable as always.

  8. Okay, not going to lie: I totally shy away from shorts. I love the looks you put together, but feel so self-conscious about my legs – much more so than when i’m wearing a skirt. But, you just may have inspired me to give them a go.

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