Styling Giveaway Winner Outfit: 9 Pieces, Dozens of Options

By Kristin Hull

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A few weeks ago we posted that Allyn Wise had won our styling giveaway and she told us about her life and fashion needs. Then, we had her create a lookbook on Pinterest in order to get an idea of her style preferences. And today, I have designed an outfit for her comprised of pieces that can all be worn together, in different combinations, and separately.

Allyn told us her biggest fashion challenge is putting together outfits for work and what we noticed from her lookbook was that her office outfit preferences were quite different from her casual ones. We thought perhaps if she could start purchasing pieces that would work for both it would increase her wardrobe options as well as make it easier to put an outfit together on a daily basis.

Keeping all of that in mind, as well as her ever present mom needs, I found several pieces that may just fit her aesthetic as well as her lifestyle. I set them up as a work outfit since that is where she has the most trouble but every piece can easily be paired with something as casual as a pair of ripped jeans.

Let’s take a look at each piece individually.

Houndstooth Skirt ($19.33/Sheinside – free shipping and exchanges, easy returns): Since moms have to sit on a variety of surfaces (depending on which role they’re playing at the time) I chose a skirt that has a lot of black in it to help hide dirt but still took Allyn’s fondness for black and white and striped garments into consideration. The pleats give it some shape and conceal the tummy while the higher waist prevents muffin top. Plus, houndstooth is a big trend for spring! (Note: this skirt comes from a company called Sheinside, one of several Asian companies selling adorable clothing at very low prices. I was leery to feature them on TMS until I watched several YouTube videos by bloggers who have purchased from them. They all said the quality was quite good especially for the low prices and that while yes, it does take a few weeks to receive a shipment, it was worth the wait. There are also customer reviews which are extremely helpful. Sizes can vary from one item to the next so be sure to look at the size reference on each item’s page and check the reviews as they often include valuable fit information.)

Denim Shirt ($59.95/The Gap)Every mom should own a denim shirt. They look chic no matter where you are or what you’re doing. They’re easily washable and they hide dirt. Wear one by itself with the houndstooth skirt or layer it over a pretty colored tank with the first several buttons open. (Check out our “How to Wear Denim Shirts” article here.) Watch Jenna Lyons, President of J. Crew, show us how to roll up shirt sleeves the cool J. Crew way (forward to the :59 mark).

V-neck Sweater ($22.99/Target): Pair a sweater in a pretty color with the skirt – try it tucked in or with a partial tuck like the photo in this post. Or try it over the denim shirt with cuffs folded up and the bottom hanging out like in the photo below.

Click photo for source.
Click photo for source.

Blazer ($29.90/Forever 21): A blazer gives any outfit instant sophistication. Layer it over a graphic tee, a colorful tank, or the denim shirt and/or sweater.

Necklace ($49.50/Guess): A statement necklace helps finish off an outfit with panache.

Sneakers ($64.95/Nordstrom – free shipping both ways, return for a full refund even after they’ve been worn): These will be well worth the money. You will have countless opportunities to wear them.

Espadrille Flats ($47.95/Nordstrom – free shipping both ways, return for a full refund even after they’ve been worn): For a backyard barbeque or a chid’s birthday party, these adorable espadrilles that tie around the ankle will keep you looking put together.

Quilted Flats ($59.95/Nordstrom –  free shipping both ways, return for a full refund even after they’ve been worn)Instead of the usual black, slip on a pair of classic silver ballet flats.

Patent Wedge Pumps ($26.24/Target – free shipping both ways): Whether you’re running around the office or running after the kids, a wedge heel is more comfortable and stable than a skinny one.

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