How Do I Dress Casual yet Chic: What To Wear On A Night Out With My Friends

by Jane

Wrap Cardigan from Lulu's

Wrap Cardigan from Lulu's

I am a working woman, and I don't have a lot to wear for casual outings. I don't what to wear. It will be cold and I have to be comfortable because we're going to a lot of places. I am 22, a warm spring, 5'8", hourglass figure, and oval face shape. Please help me figure out what to wear.


Looking casual means wearing clothes that are looser-fitted and shoes with a flat or short heel, without any complicated or fancy details. Just plain neutral.

I recommend you to secure these basic wardrobe essentials which are quite casual and versatile:


  • Dark wash and black jeans (skinny if you don't have problems showing off your hourglass figure, straight and bootcut if you want to tone it down)

  • V-neck tees in your colors (and of course black even though it may look harsh on your Warm Spring complexion. Remember to add a nice scarf in your best colors to brighten it up)

  • A shawl/scarf in your personal color (to keep you warm and add some color to your cheeks)

  • A black or dark brown boyfriend cardigan (not one of those button-up kinds, but something that is slightly loose-fitted with a low neckline)

  • Flat ankle or mid calf boots in black or brown

  • White or black plimsolls (canvas sneakers)

  • Black wrap dress

  • Black opaque or wool tights (to go with your casual dresses, like the wrap dress)

  • Black or dark brown leather jacket (if it's cold swap it up with a warm trench/pea coat)

  • Leather hobo bag

They're very basic and easy to mix and match. Add a couple of accessories (a print scarf, bracelets, hoop earrings, etc.) of your personal style to look trendy.

Here are some outfit ideas for you (using the items mentioned):

How to Look Casual in Chic During Winter



Casual versatile basic outfits


Look #1
Black v-neck tee with a cute brown belted cardigan, straight leg jeans and tan brown flat leather boots

Look #2
Gray t-shirt, jeans, black boyfriend cardigan and a cream (not crisp white as it doesn't flatter your complexion) and black canvas shoes

Look #3
Black v-neck wool sweater, jeans, brown belt wrapped around your waist and ankle boots.

Look #4
Black v-neck wool sweater, brown knit vest with brown skinny belt, jeans and brown suede knee boots

Look #5
Black wrap dress, opaque tights and black knee leather boots with wedge heel. If it's really cold outside you can swap up the wrap dress with a knit turtleneck sweater dress

As you can see the outfits are very simple so you can just switch the pieces and double the combinations. Or just add a trendy jewelry piece.

If you and your friends are planning to eat at a restaurant later that night then you can drop the tee and go for a dressy blouse or top with your sweater.

I included belt details because I think it will emphasize your hourglass body shape.

Hope I gave you some ideas!


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More Shopping & Chic Inspiration at the TCF Blog:
The Chic Fashionista's Latest Trends Picks - Chic Runway Looks and Must-have Trends and Trendessentials The Chic Fashionista's Chic Inspiration-blog - Outfit ideas, celeb style and trend styling tips The Chic Fashionista's Stylish Finds - Latest trends and shopping picks, sales & discounts, link round-ups and featured posts & blogs/sites Learn more about the fashion basics on how to look your best and dress stylish

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