Celebrity Stylist Denise Caldwell Shares Her Top Winter Style Tips For Curvy Girls

She has worked along side some of the most reputable editors for magazines such as Vogue and Harpers Bazaar. Today, Denise Caldwell devotes her time to working with every day women helping them be their best and most beautiful self.

We caught up with this busy young lady to chat fashion, layering and being confident in your own skin.

Maddy: You have an impressive resume, and a great sense of style. Were you “born” a fashionista?

Denise: I’ve always been a curvy woman, you know I always say this; my parents dressed me for five years, the other twenty six I’ve been dressing myself, so it “kinda” makes sense that I would have this innate connection with curvy plus size women.

Maddy: I’ve seen your segments on TV and they always look like so much fun. How did you go from on-set stylist to on-air style expert?

Denise: I would meet a lot of the producers and they would say “Hey, you’d be great on TV, have you ever thought about it?” And I kind of was just like, you know, it interests me, but I want to find out more about it. Once I got my first appearance on Good Day New York, it kind of really catapulted into “hey, there’s something with this style expert”, and from there, I’ve been able to be featured on Dr. Oz, The Today Show, HLN and CNN, and with media presence, I was able to work with various brands like Fruit of the Loom and Fit For Me, when they were relaunching their brand, they thought of me as a brand ambassador.


Maddy: Let’s chat layering and winter fashion… Layering sounds bulky to many of us can you address the purpose of layering and how to do it the right way?

DC: Absolutely! So, the first thing I talk about with layering is you basically want to play the game on how to layer. You can definitely have too many layers, which is why it’s important to look at the details. Consider ruching or draping if you have an area that you want to conceal. Sometimes, people forget about those target areas, they’re like “okay, which one do I choose to drape, and which one do I choose to be more form fitting?” The draped parts will always be the parts you’re trying to conceal. I call it the WIP, the “work in progress” area. That’s where you want to drape because it’s the area you’re working on. The part that you want to flaunt should be the more form fitting part. Choose great fabrics, like spandex and cotton/polyester. That combination together is always your best friend, because that will allow fabrics to be smooth and lay over your body.

MJ: Perfect! So, let’s discuss winter fashion trends and styling tips.

DC: There’s so many great trends. I always think that curvy, plus size women who read your magazine love fashion—they go to you guys because you’re the source of the curvy/plus woman, which is amazing, but sometimes they may see stuff and say “oh, the model did that, but I don’t know if I can.” I came up with a thing called my curvy translation. You take one portion of a trend and you use that. For example, let’s say you want to do plaid. Plaid is big, and transfers all year, especially with the holidays. You may be intimidated with doing head to toe plaid, but you can wear a plaid shirt, skirt, cardigan, or sweater, and that’s your “wow” piece. Your base stuff is very simplistic. I always say wear color! So let’s say your plaid is a navy plaid. You can maybe mix grey with that, or navy blue. So your leggings or pants may be blue, and your plaid shirt, and then your cardigan is navy blue as well. You still give a little “umph” with it. Or, you reverse it: your cardigan is plaid, or your sweater, or any pattern (such as paisley or checker print), and then your base is still in that same color palette. If you go with, once again, blue, then your base can be blue as well. So, if you do a pencil skirt with that, and a collared button down with it, and still have the sweater layered over it. You could also wear all one monochrome color but have a plaid belt. It’s all about mixing and throwing a little accent in.

Maddy: I know we have discussed skirts in the past and I love your take on hemlines and proportions. Can you share with us?

Denise: There are four skirt styles a woman should have for winter. I think hemlines are great for proportions of the body. The midi skirt has been a trend and it’s been great for curvy women because it hits right at the calf. Depending on your height, it should go about two inches below your knee. The maxi skirt—everyone should have one in their closet—it’ll keep you warm and it’s also slimming. When you think about the hem of a maxi skirt, it should hit you right at your ankle, regardless of your size. I want people to try a mini skirt for winter! Layer it up with a legging or something underneath, you’ll look amazing and show off your legs. The must have is a pencil skirt. I call that my “cadillac” of skirts. It’s going to suck you in; it’s going to cinch you in all the right places. That’s definitely a universal skirt that any woman, any size, any height, can wear and it’s complimentary. It goes from day to night, and still looks amazing.


Underneath, wear a brief underwear that’s seamless. Fit For Me by Fruit of the Loom has some great pieces to go underneath more form fitting outfits. Skinny jeans, pencil skirts, I always say to wear a brief instead of a thong. Wear something that’s going to keep you comfortable and also confident while you’re working your cute outfit.


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