I want to feel more confident and alluring in my date night outfits. Help me get dressed for Valentine’s Day!

“For Valentines’s Day this year, I want to go out and feel sexy and confident in my outfit, but I’m not sure where to start. What are some pieces I could buy for the occasion?” —Annaliese

When you feel sexy and confident from within, that’s when you come into your power. Owning who you are and identifying the clothing that enhances these feelings is the key to finding confidence-building looks that you’ll wear on repeat.And whether you’ll be going out on a dinner date with a partner, staying cosy at home or spending an evening with your gals, Valentine’s Day serves as the perfect excuse to figure out the outfits that will always help you look and feel your best.

Contrary to the stereotypes associated with dressing for date night, there is no one way to achieve a sexy and confident look. Finding pieces that align with your specific version of sexy and confident is empowering and will be unique to you. So how do you determine what pieces make you feel this way?

Whenever you feel good in an outfit, take a second to document it. Snap a quick mirror selfie and add it to an ‘Outfits’ album on your phone. Whenever you don’t know what to wear, browse this album for inspiration, and to help guide your looks. Once you’ve accumulated a few months’ worth of outfits, the album will serve as a database. Analyze the pics to find common pieces, colours and silhouettes that re-emerge throughout your looks — these are your confidence boosters.

Instead of thinking about what you want to hide when getting dressed, focus on what you want to showcase. This shift in mindset will help you to see yourself in a more positive light and can help you navigate dressing to feel great, whether it’s for a special occasion or for everyday.

Feeling sexy isn’t only about the clothes others can see; it starts with your undergarments. That old, plain bra you’ve worn a million times probably isn’t making you feel much of anything. Perhaps it’s time to retire it, and look for lingerie and undergarments that you find comfortable and stylish and start wearing them often, for yourself.

A new standout piece can be an outfit-maker, but when you buy something for an occasion, it’s important to remember to keep wearability and versatility in mind. Before buying anything, make sure you can make at least three other outfits with the new piece and items you already have in your wardrobe.

Having followed these steps for many years, I’ve become very attuned to what pieces make me feel confident. As someone who focuses on highlighting their legs, for me, it’s all about skirts and a great heel. For some of my clients, it’s a bodycon dress to highlight their hourglass figure, whereas for others it might be a slouchy blazer, well-fitting denim or a pop of colour via an accessory. The fun is in figuring out what does it for you.

Discovering the pieces you feel your best in takes time. Be patient with yourself and don't be afraid to try something new! To help you get started in your journey I’ve rounded up a few confidence-boosting, Valentine’s Day-ready looks.

Daring date night

J.Crew dress, $188, jcrew.com SHOP HERE

It’s all about fabric! A little bit of silk, a touch of velvet or lace or some sheer detailing can make any simple look feel sexy. A silky-textured slip dress in particular is so versatile: it can be worn on its own, as a skirt when layered underneath a sweater or cardigan or belted with a blazer.

Jennifer Behr bow, $128, shopbop.com SHOP HERE

Clip-on bows have emerged back onto the styling scene in a big way this season. We are seeing them not only worn dressed up with evening wear but also with denim, a tee and a blazer. Add them to a ponytail or updo or pin one to your sweater or coat as a brooch.

BaubleBar earrings, $48, baublebar.com SHOP HERE

A sparkly piece of jewelry can instantly take an outfit from simple to special. These subtly heart-shaped earrings sway with fun crystal fringe and draw the eye to your face.

Zara boots, $149, zara.com SHOP HERE

Instead of bright red and pink, opt for a more subtle Valentine’s colour combo: burgundy and navy. This can be as easy as pairing dark denim and a navy top with a statement boot, and will work from day to night for any of your Galentine’s adventures.

Aritzia camisole, $58, aritzia.com SHOP HERE

Worried your bra and/or bra straps will show under a cowl-neck cami? We’re here to let you know that it’s OK. Go with a soft bra with a little bit of lace, this will actually add a feminine touch to the look.

DL1961 jeans, $245, holtrenfrew.com SHOP HERE

Straight-leg jeans in a deep, dark wash will feel right for almost any occasion, and tuck perfectly into a wow-factor knee-high boot.

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Ask The Kit is the weekly column that will solve your style, grooming and etiquette dilemmas with our panel of experts. Once a month, personal shopper Julianne Costigan, The Kit’s stylist-at-large and author of the shopping resource The Digital Style Guide answers your fashion questions, giving you real solutions for building a functional, stylish wardrobe. How can I dress well at my new job? How do I establish my very own “uniform”? Send your Qs to ask@thekit.ca