I love the way today’s fashion celebrates an infinite variety of stylish possibilities. More than ever before, we are living in a fashion era that is ultra accepting and encouraging of all sorts of outfit juxtapositions and silhouettes. We celebrate personal styles from the super classic to the ultra avant-garde and everything in-between.

Trends also have much longer fashion lives than they used to have. In fact, fads barely exist these days because things can often be worn in updated ways.

Gone are the days when looking stylish meant dressing in one particular way. This is truly refreshing and liberating.

We have reached the stage in fashion where sweatshirts can look sassy. That’s quite an achievement! I’ve won some clients over to sassy sweatshirts because they are comfortable and un-fussy. Also: machine washable. 

Two points are critical in order to get the modern and fashion forward vibe of the sassy sweatshirt right:

1. Choose the right sweatshirt shape: You’re after a basic sweater style in sweatshirt material. No traditional zippered hoodie type styling because that looks too much like loungewear or sports gear.
2. Wear the sweatshirt like a sweater: The photos below show sassy sweatshirts styled in ways that work to my eye. I like them worn casually with denim, and a little dressier with trousers and a flared skirt. I also like the pairing with leather bottoms, heels and a clutch. Adding a sophisticated edge to the outfit makes the sweatshirt look modern and intentional. 

Personally, I’d still rather wear a real sweater than a sassy sweatshirt because I bat for Team Dressy. A fine gauge knitted pullover is dressy whereas sweatshirt fabric is casual no matter how you slice and dice it. That said, the outfits with the leather pencil skirts are appealing to me because the juxtaposition of items is extreme to the extent that they work in harmony. I wouldn’t say no to sporting a similar look with pearls instead of a cuff, just for fun. 

What’s your impression of the sassy sweatshirt? Fashion forward or awful?

This poll is for all pump wearers. You are on Team Closed Toe Pump if you prefer to wear closed toe pumps. You are on Team Peep-Toe Pump if you prefer to wear pumps with peep-toe toe box detailing. ALL styles of pump count for this poll, be they stacked heels, stilettos, mary janes, wedges, low heels, high heels or platforms. 

I am on Team Closed Toe Pump because peep-toes rub my toes and give me blisters no matter what. I have a pair of peep-toe oxfords that I can wear for about four hours and that’s with body glide, but no peep-toe pumps at all. I like the look of a peeping toe, but my fussy feet won’t have it. 

Over to you. Are you Team Closed Toe Pump or Team Peep Toe Pump? Tell us why and no batting for both teams.

A useful way to determine whether an item deserves a place in your wardrobe is by assessing its style potential on three levels. First, assess the piece as an item. Second, assess it as one part of an outfit. Third, assess it as a component in one or more wardrobe capsules. Applying the “item-outfit-capsule test” helps you to make more informed decisions. This is how to eliminate closet orphans, ensure easy outfit integration, and get the biggest bang for your fashion buck. 

By way of example, here’s how I recently used the item-outfit-capsule test to determine whether this Rebecca Taylor combo sweater deserved a place in my wardrobe. We were in Neiman Marcus. Greg had just spotted the item and had offered to buy it for my birthday.

Let the testing process begin: 

Item

First I assessed whether the piece was flattering and comfortable, worked for my lifestyle, was aligned with my current style goals, and whether I felt fab wearing it. YES was my response to all of these questions. I loved the colour, the non-itchy warmth factor, the simple design, the modern cut, the mixed use of fabrications, the refined gauge of the knit, the dropped shoulder seams and the high neckline. The item was off to a good start earning a spot in my wardrobe. 

Outfit

Next I imagined how I would style the item in an outfit. The first thing that grabbed me was that the item can be dressed up or down because of its fine gauge knit. Wearing it with jeans is a no-brainer, but I asked myself which non-denim bottoms would work with this style of pullover. I came up with cigarette pants, wide tailored trousers, slouchy tapered trousers, classic bootcut trousers, cropped pants, pencil skirts and harem pants. Check. I have all these bottoms covered in my wardrobe. 

I realized that I would not be able wear my tailored blazers over the sweater because it’s too bulky, but that’s okay because I could wear it over a white button down shirt and add a leather jacket or coat for insulation. Sorted. Purchasing this sweater was still an option.

Capsule

Finally, I thought about how the sweater would work across a few wardrobe capsules. A capsule is a group of wardrobe items that work together, and nothing more complicated than that. I wear a lot of black, white and cream and have an assortment of both dressy and casual items in these neutrals. I love this sweater’s shade of blue with black, white and cream so it fits right into capsules that are built around those colours. And because of the styling details, the sweater would work in both casual and dressy capsules. 

I could also see the sweater working with my smaller but growing citron and tomato red capsules. Throw in patterns like stripes, checks, dots and animal print and the mix-and-match possibilities just kept on growing. 

After having these conversations with myself in the dressing room, this piece passed the item-outfit-capsule test with flying colours. The sweater has earned a well deserved spot in my wardrobe and I’m excited to wear it as soon as the weather cools. 

Although this particular piece has a multitude of styling possibilities with the items already in my wardrobe, that needn’t be the case for all new purchases. It’s totally fine to bring home an item, or keep an existing one, with the intention of purchasing more to wear with it over time. That’s why we think in terms of wardrobe capsules. The point is that it’s worthwhile to think through these questions before you commit to keeping an item. That way you’ll know how to wear it and what you need in order to enjoy it to its fullest.