This season I’m all about investment dressing.
I think it’s important to find a handful of quality pieces in your wardrobe that you can style a few different ways. Not only are you getting more bang for your buck but you’re also creating a paired down wardrobe. There’s no need to have tons of new clothes every single season. Buy a few key pieces that will take you through at least two seasons or possibly more.
I was eager to collaborate with Winged Monkey in Westport, CT as their expansive boutique literally has everything.
From kids clothes to evening gowns, they have you covered! In business for over 20 years, mother/daughter duo Cathy & Jenny have created such a cool atmosphere for shoppers. There are items that will fit everyone’s price point, as well as accessories, shoes & gifts! All of the clothing in Winged Monkey is definitely on the more fashion forward side but they also have great basic tees, sweatshirts & lounge wear. What attracted me to Winged Monkey was their dedication to finding the perfect outfit for the client. Every time I’ve been in their store, the staff worked alongside each customer to pull options based on the client’s needs. Cathy even got me to try on a few things that were outside my norm (sorry but still not giving into the crop top LOL).
I was able to find a handful of pieces (all priced below $150 each) to create a few different looks. Each look can also be taken from day to night with just a switch of shoes or jewelry! It honestly really pays to invest in at least three good pieces each season & then build different looks with these pieces. Check out some looks I put together below (everything can be purchased at Winged Monkey- call or check out their website)!
For my first look, I paired faux fur leggings ($98) with a long oversized sweater ($88). I love the neutral tone of this sweater because I could wear this with literally everything (and in multiple seasons since it’s not too heavy). Add sneakers for a day of running errands or a lunch date with girlfriends. I’m totally loving these sneakers ($99) with all the different textures and prints going on. Sneakers that are a bit dressier than regular everywhere athletic wear elevates an outfit. I also paired a long pendant necklace made by Queens Beads (only $58) with this outfit, just to add a bit of bling.
To take this look from day to night- I added a faux fur vest ($134), some black heels. Easy & elegant! I still felt comfortable but trendy at the same time. Keep reading to see how I paired this sweater & vest with other options! For reference, I was able to size down due to the oversized nature of this sweater (wearing a medium).
Next up- taking this sweater to a new level & pairing it with the cutest maxi skirt.
Let me just say, I am not a huge fan of skirts. For some reason, I feel like they don’t fit me right or are way too long on me. BUT this skirt ($89), was just the right amount of sweetness & had the most comfortable elastic waistband. I’ve been searching for something snakeskin print for a while, but haven’t loved anything. The print on the skirt is so subtle that it will totally carry over from season to season & continue to stay relevant.
The pink tone of the sweater matched perfectly with the skirt as well! You would think this skirt could only be worn during the spring/summer- but just pop a sweater on & it takes you through the colder months. In the spring/summer, I would wear a white tee with this & then you could also layer a denim jacket on top. Or a cute cropped white moto jacket. The possibilities are endless. I paired this outfit with some white sneakers, because comfort is everything. You can add some cute taupe or grey booties to dress this up a bit OR add a headband (which Winged Monkey has a huge assortment of).
My final look is one that is the most my style & comfort level- denim!!
These Spanx jeggings ($128) are the BEST thing ever. Coming in at just over $100, this pair of denim is definitely worth the money. There is an elastic panel around the tummy that sucks you in without making you feel uncomfortable. The amount of stretch is perfect. And the raw hem detail is SO in right now. I’m wearing an XL so I would say these fit pretty true to size. I paired the slightly distressed denim with a plain black turtleneck & the same faux fur vest ($134) I was wearing previously. Again, switching my footwear took this outfit from day to night!
My suggestion is to invest in three pieces every season that are versatile & transitional through seasons. Pick a top (such as a sweater or coat), a pair of pants (my vote will always be for a good pair of denim) & a dressier piece (such as a skirt or dress). Look for items that will already work well with items you already have in your closet. Envision these outfits before you pull the trigger & purchase these items. Save your money on trendier fashion pieces that most likely won’t be wearable next season & buy inexpensive versions.
And lastly, shop your local boutiques first before immediately going to big box retailers. Many of these small shops carry quality clothing & options you just won’t find in a larger department store. PLUS the customer service you will get at a smaller boutique just does not compare! Cathy & Jenny are extremely knowledgeable when it comes to what vendors they carry & how items fit. They will go above & beyond to find you whatever you are looking for. Stop into Winged Monkey in Westport, CT today or if you are not local- you can shop their website or call to order!
