Nikki’s Inbox: From Tomboy To Girly

When I was younger, I used to be a bit of a tomboy and dress like that too. But now I want to change my wardrobe to become more feminine. I would like to start wearing skirts and dresses but I don’t want to wear anything extremely girly so I don’t feel too out of my comfort zone. Also if I wore a skirt, what else would I wear with it!? Can you help me please? Thank you.

Rebecca, 20/United Kingdom


I’m glad you’re trying to get out of your comfort zone, Rebecca, and baby steps are fine. I don’t see anything wrong if you prefer wearing jeans, T-shirts and shorts to dresses and skirts. Except for a few things that I personally think people should stop wearing at a certain age, there’s no rule that says wearing dresses or having long hair means you’re feminine, or that men should wear a beard and pants all the time to look masculine. Be yourself.

Fit, Lengths and Fabrics

A few things to keep in mind since I have no idea about your body measurements. The length and fit of your new clothes depend on both your horizontal and vertical body shape. Mini and midi-length skirts and dresses look better on petites. Fit is very sacred because it’s what makes you look good instead of the prices or labels of your clothing. Fabric is something you also have to consider when it comes to dressing for the season. To figure out all these, check your existing wardrobe. Anything that’s too long or too big, please donate to a charity if they’re still wearable. For the ones that still fits you well, ask a friend for an objective opinion, and have them measure your dimensions, too.

It’s always about the RIGHT FIT.

What to wear with a skirt? Anything!

Any top goes with a skirt. What you wear as a top also changes the vibe of your entire outfit. A simple colored T-shirt or tank is definitely casual. An off-shoulder blouse makes it look flirty and playful. A classy button-down shirt speaks easy elegance while a crop top or distressed top spells edgy. If you’re going to pick out a skirt, why not try a denim skirt so it feels familiar? A knee-length, A-line version — which suits most body shapes and heights— will be a nice starting point. Team it with a simple sweater and sneakers or flats.

The Right Dresses

As with skirts, you also have to keep in mind your dimensions for the fit and length of your dresses, as well as fabrics to some extent. Some fabrics may be too clingy to the body and emphasize all the areas you want to downplay. Some may be unsuitable for the weather or season. So dress well and dress smartly! The advantage of a dress over a skirt is that you don’t have to worry about what else goes with it, save for accessories (if you want) and shoes. Below are a few styles you might want to try.

Jumper Dresses

British folks like you, Rebecca, refer to this as a pinafore or pinny dress. The jumper dress, as I call it, has been enjoying renewed popularity because it’s so easy to wear! You only need to wear it with a base layer — any top will do — and that’s it! Jumper dresses also come in various silhouettes so don’t limit yourself. If you want a classic look, an A-line style with a defined waist and lower neckline will do. You can also look into long-line cuts that hit your knees and with a ruffled hem. Depending on the fabric, you can most definitely wear jumper dresses and skirts all year if you want!

Mock Two-Piece Dresses

A mock two-piece dress saves you the time and agony of mixing and matching. Some dresses have the top and skirt in complementary or tonal colors, while others look distinctive from each other so it’s up to you. You can look up these styles online or in stores, and replicate the look with your own separates.

Sweater Dresses

This is my seasonal example for you, darling. Sweater dresses come in figure-hugging and loose/relaxed silhouettes. Go for something in between — comfortable yet with a good fit. A belt is your best friend when it comes to sweater dresses so you can define your waist and avoid looking shapeless. A knit sweater dress is also a great way to play with textures. Add a leather jacket to the mix, and suede ankle boots for a nice finish.

Here’s to achieving more style goals!

P.S. If you’re sending a question, please don’t forget to include any helpful information about your body type or shape, your tastes or personality. You can include a selfie (link only please) or a photo of your clothes (which I will never publish without pre-approval). Thank you!

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