Ask Allie: Day to Play Styling of a Dress

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Allie, can you help me with some “Day to Play” looks? You do this effortlessly, but I am clueless on how to make a dress work for the office and then for a date or after-work event. Help!

Can you suggest some work to play looks on your blog? Thinking how to dress for the office and do a change for a night out.

I'm back on the dating scene after eight years in a monogamous relationship. Most dates end up being drinks, coffee, or dinner right after work and I have NO CLUE how to dress for the office and also to impress a man. Do I just toss a pair of heels in my commuter bag? Will they understand if I show up in work clothes or will they think I am an old fuddy duddy? HELP!

For a dress to really work as day to play, and not a dressy dress trying to look office-appropriate or a work dress trying to glam it up with new shoes, it’s best to go with a solid color and a substantial fabric. While matte jersey may be one of my favorite fabrics on the planet and I love me a drapey fabric, unless it’s a traditional corporate silhouette (collared wrap dress, shirtdress) such material can look too dressy for the office. While there is many the print cocktail dress on the market, printed fabrics that are appropriate for the office are rarely also appropriate for the night club (and vice versa). I have had the best success with a solid dress with short to bracelet length sleeves, and of a heavyweight knit or a versatile seasonless fabric like gabardine or crepe.

Below are some dresses from Nordstrom (all under $150) that I think fit the bill for being great for day to play – dresses that can look fabulous in the boardroom, but also quite sassy on the dancefloor. A quick change of accessories is all you need for your complete transformation – here are some suggestions on how to make these dresses day to play appropriate.

Maggy London Belted Ponte Knit Dress

I love dresses like this because they are so versatile. While it is sleeveless, it’s a fabric that works year-round so you can layer with a blazer or cardigan for the office, and remove for your night out.

The first look would be great for work, but also be a wonderful choice for happy hour or a casual get together.  The cardigan will keep you comfortable as the temperature drops but can easily be taken off without ruining the look.  With such a fun cardigan, it's good to keep the rest of the ensemble pretty classic – flat riding boots, a classic bag, and simple gold link bracelet.

For a fashionable night out, tuck these accessories in your commuter bag for a quick transformation.  The dalmatian print belt is a bit wider than the one that comes with the dress and will better emphasize the fit and flare silhouette.  A bold gold cuff, platform heels in a modern shape, and a simple handbag with gold details pulls the ensemble together for a look that would be great anywhere from a first date to a rehearsal dinner.

The final ensemble shows how you can really dress up this workplace dress – with delicate, feminine, and sparkly accessories this dress is ready for the theater or a Friday night wedding.  Since the belt doubles as jewelry, there's no need for much more bling – a simple bracelet with pavé balls is enough to tie it all together.  Choosing a clutch bag automatically dresses up the entire look.

I have practically the same dress, bought last year at Ann Taylor. I can attest to the fact that this dress can dress up and down with ease. The ponte fabric will hold up through the workday, resisting creasing and wrinkling. Pockets are always a nice addition to dresses, and can benefit you greatly if you switch to a smaller dressier bag for the evening.

For this combination, I showed how you don't need to change every accessory to transform a look from office to after hours.  For the day look, I used the popular “bubble” necklace in black with classic pumps and a structured leather tote.  Simple, on-trend, but work appropriate.

For the second look, I kept the necklace, added a bold bracelet, fun heels, and a conversation-starting clutch.  The necklace is versatile enough that when paired with more festive of shoes and bag, it goes from day to night with ease.

The final look is a bit more dressy and polished; shiny gold bracelet and necklace make a sophisticated statement and work great with the same pumps worn to the office.  A clutch in the same polished leather and in a classic shape makes the heels look purposeful and more dressy.

The style of this dress is so on-trend yet also quite classic; such details make styling easy. No need for a ton of accessories and changes to dress up or down this frock, it speaks for itself with the drop waist, seaming, and pocket flaps. While both colors are fabulous, I am partial to Tomato which can transform more drastically with the change in shoe or jewelry.

This dress is the type that would work just fine with a pair of pumps or boots, so I got a bit more creative with my options.  The top two would work for a creative or more laid-back office as well as a night out.  While both are pretty simple, details like the nude fishnets or wedge booties kick it up a notch, and make the look great for after-work cocktails as well as spending the day in the office.

The third look shows how you can really glam up the dress for a more formal date or function.  The nude and pearl combination is subtle and sophisticated and lets the details of the dress shine.

Another statement maker, this dress stands out with the fabulous shoulder detail. Though the pleated shoulders are memorable, the rest of the dress is quite simple, making it versatile and wearable for years to come.

For the day look, I kept it simple with opaque black tights and booties and simple enamel bracelet.  If your office allows it, you could easily switch for a more funky/glam bootie to make your after-hours quick change simpler.

For these options, I used color to transform the dress from day to play; often an extra coat of mascara or a switch to a bold lip can be all you need to look more festive and fun.  The first look is taking advantage of the graphic shoulders of the dress, creating a tough-gal ensemble with rocker-inspired accessories and a bold red lip.

The third look takes the  popular neon trend and shows how it can easily be added to a piece already in your closet.  Hot pink heels will stay stylish after the neon trend has passed, and a neon clutch will still make a fab statement with a LBD after highlighter colors are out of the stores.  A bold pink lip and a budget-friendly neon statement necklace complete the look (FYI no need to buy a neon necklace, you can DIY for less).


These collections are merely suggestions -I found that by taking the dress and putting it into Polyvore I could think of multiple ways to accessorize them for day as well as for play.  If you are having trouble imagining pieces together, consider playing in Polyvore – you can clip anything on the Web to Polyvore and have it in “My Items” ready for you to use in a set.  It's a fun and free online tool for making pretty collages… and also imagining new ensembles for your wardrobe!

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