Style Smart: New Ways To Rock Holiday Dresses

Nail the layering game with these tips

The countdown to the holidays has officially begun, and that means shopping for festive attire that will put you in a celebratory mood. This year, why not “shop” from your own wardrobe and breathe new life into your classic holiday dresses? Here are four fun ways to rock holiday dresses beyond the festive season — and without the use of your usual “slip dress and stilettos” formula.

Velvet frock with an oversized sweater

We have no doubt that The Attico founder and fashion influencer Gilda Ambrosio has the chops and confidence to pull off velvet for daytime affairs. However, she’s taken her ensemble up a notch by pairing it with an oversized lilac sweater and the result’s pretty stunning. In fact, it’s a fun and more comfortable way for us to incorporate dressier fabrics into casual settings.

For more inspiration, click here to check out fashion content creator Andy Torres’ outfit, where she paired her embellished velvet frock with a heavy knit sweater and ankle boots. 

Reformation Minna Velvet Dress and COS Oversized Teddy-Knit Sweater

Left - Reformation 'Minna' Velvet Dress, ~USD273.16 (; Right - COS Oversized Teddy-Knit Sweater, USD89 (

Style it: Break out your velvet mini dress (or add this Reformation velvet dress to cart) and let it have its moment to shine in your daily get-ups. Make the dress appropriate for coffee dates and lunchtime meet-ups with friends by pairing this with an oversized roundneck sweater, such as this number by COS. Complete the look with sunnies, a pair of off-white canvas sneakers and a cotton tote bag.  

Button-down maxi with high-waisted trousers

Button-down maxi dresses are a wardrobe staple, especially with their flattering v-shaped neckline design. If you wish to rock these on the regular, consider following creative director Emili Sindlev’s lead by applying her useful style formula: button your dress from the top until your midriff and layer a pair of high-waisted trousers underneath it. This gives you more ease of movement as well. 

Nasty Gal Plus Size V Neck Midi Dress and & Other Stories Bootcut Jeans

Left - Nasty Gal Plus Size V Neck Midi Dress, USD27.2 (; Right - & Other Stories Bootcut High Waist Jeans, USD99 (

Style it: Having trouble finding a maxi that fits your petite frame? Opt for a midi dress instead if needed — it still works in this context. Pick out your button-down dress or treat yourself to this lovely lilac midi dress from Nasty Gal. But before that, hop into these candy pink high waist jeans from & Other Stories, which are slightly flared at the bottom to add a little more charm to your outfit. Top it all off with a trendy mini purse. 

Slip dress with a bolero

Slip dresses do a fine job in showing off one’s curves and are perfect for dinner parties. That said, they are often made of silky, sheer fabric and tend to offer minimal coverage around your neck, shoulders and chest. On this note, we found San Francisco-based content creator Allison Ho’s styling solution to be quite smart. She paired her champagne silk dress with a black bolero to keep her arms covered. It’s also a good styling tip for those who are a little conscious about their arms. 

Tobi Satin Cowl Neck Dress in Sage and H&M Rib-Knit Bolero

Left - Tobi Satin Cowl Neck Dress in Sage, USD40 (; Right - H&M Rib-Knit Bolero, ~USD22.11 (

Style it: Sage looks flattering on different skin tones — whether you’re on the fairer, paler side or on the golden, tan end of the spectrum. Start with your go-to slip dress or pick up this Tobi Cowl Neck dress. Then, throw on the cream-coloured H&M rib-knit bolero when the weather gets chilly or if you prefer a little more coverage. For shoes, go with a pair of kitten heels and you’re good to go. 

Bodycon midi with a bustier top

Bodycon midi dresses are versatile enough to be worn across different settings and are especially fitting for glam occasions. But it’s always helpful to discover new ways to style them so that you extend their “lifespan” in your wardrobe. Take notes from Malaysian singer and fashionista Daiyan Trisha, who expertly styled her brown bodycon midi dress with a black bustier top. Have fun experimenting with different types of tops while you’re at it until you find one that best suits your shape and style. 

Zara Jacquard Midi Dress and Faux Leather Crop Top

Left - Zara Jacquard Midi Dress, ~USD36.84 (; Right - Zara Faux Leather Crop Top, ~USD36.84 (

Style it: We managed to ID Daiyan’s dress and bustier top, which are from Zara. Re-create Daiyan’s exact fit with these two items. Alternatively, grab your own figure-hugging frock and layer it over a black top with thin straps. Cap off this ensemble with a classic black bag. 

How do you plan to dress up for the holidays? 

(Cover photos from: and

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