Bootcut jeans and trousers are thought of as universally flattering and always in style. Generally, I agree with this statement. Bootcuts are not the on trend choice of jeans and trousers, but they are certainly not dated. They are a classic with a high longevity factor. 

As far as the style being universally flattering, I think we all have the potential to look fabulous in a pair of bootcut jeans or trousers when we find the right fit. But the jury is still out on whether they are more flattering than a pair of straight leg jeans or trousers. I do have clients who to my eye look better in bootcuts than in straight legs. Some have a relatively large bust, broad shoulder line, and narrow hips and thighs. In their case bootcuts provide volume on the lower leg, which balances out the top and bottom parts of the body. Others are pear shaped and look particularly fabulous in bootcuts because wider hems balance out the proportions of relatively larger hips and thighs. 

Although the general silhouette of bootcuts is the same, namely fitted through the thigh and flaring out on the lower leg, there are subtle differences in cut that are worth noting. First, some styles flare out more dramatically at the hems than others, and sometimes a less flared style looks more streamlined. Second, the fit on the thigh can be body con or tailored, or even on the loose side of tailored. Third, the rise can be low, mid or high. And fourth, fabric distinctions are important because they determine the dress code appropriateness and impact overall fit. Bootcuts can be made of denim, wool, wool blends, cotton blends, man-made fibres, and have some or no stretch. It’s a question of choosing which cut in a particular fabrication works best for you. 

On the whole, most of my clients are favouring skinnies, straight legs and boyfriend styles over bootcut jeans because they feel more fashionable than the classic. But dressier bootcut trousers are still being worn very regularly by my clientele, especially in business casual and business formal work environments. It’s an easy go-to trouser silhouette that always looks professional and appropriate. 

I fall into this category too. I last wore a pair of bootcut jeans in 2011 and have no desire to wear the one pair that hangs in my closet. In fact, I am thinking about passing them on because I much prefer wearing trendier straight legs and baggier styles like boyfriend jeans. That said I LOVE wearing my bootcut trousers, of which I have three pairs. There is something about wearing bootcuts in dressy fabrications that tickles my fancy more than wearing a similar silhouette in denim. I feel elegant in a pair of bootcut trousers, but ever so slightly frumpy in bootcut jeans. 

Over to you. Do you think bootcuts are universally flattering? Do you wear bootcut jeans and trousers? If so, why do you like wearing bootcuts? If not, why do you prefer other styles of jeans and trousers to bootcuts?

Some of these items are very bohemian, while others have just a touch of boho. Remember that you don’t need to wear a bohemian vibe from head to toe. Mix it up with crisp classics, arty elegance or a fun androgynous look. Browse through all the colour options.  

1. Hinge Embroidered Denim Jacket: The least bohemian item on this list. Some of my clients, with a graphic and crisp modern classic style, have loved this white topper so that’s telling. The embroidery is subtle and the front hem dips down to achieve a fabulously flattering silhouette.
2. Leith Grunge Open Crochet Pullover: Wear it over a tank top with a pair of boyfriend jeans or a full skirt. Fab with a casual pencil skirt too. 
3. Splendid Draped Thermal Hoodie: Cozy, casual and covered. Ideal for the beach, plane travel, Mums on the go, or working from home. 
4. Free People Embroidered Crochet Trim High/Low Dress: This frock is especially great in motion. Theatrical, interesting, and drapes quite nicely. It’s a lot of dress so consider yourself warned. 
5. Free People Wild Wind Top: An updated empire cut blouse with lace trim and dramatic sleeves. Check out the great back detail. They’ve even semi-tucked the silhouette in the photo, which is unexpectedly fab. 
6. Free People Sunblock Mesh Knit Cardigan: Boho deluxe! Like the way it’s been styled on the model. Perfect for Team Tall. 
7. Trouve Print Tunic Tee: A mixed media silky tee with a subtle pattern and fun high-low hemline. 
8. Free People Krispy Mesh Peacoat: A relaxed and breezy decorative topper. 
9. Sanctuary Mariposa Streak Print Chiffon Top: Gorgeous on broad shoulders and forgiving on the midsection. Kimono-esque. 
10. Betsey Johnson Floral Fringe Tote: A fringed bag with a touch of glitz. 
11. Freebird by Steven Phoenix Boot: A tie-dye bootie for Team Rough and Rugged. 
12. Pikolinos Paris Bootie: A structured earthy sandal bootie that is comfy and versatile. 
13. Frye Cameron Shoulder Bag: This type of bag improves with age and is always in style.
14. Ralph Lauren Leather Belt: Simply earthy and versatile in either colour. 
15. Rebecca Minkoff Hugo Silk Pants: And we’re ending off with another piece that’s fab in motion. Alluring, ’70s glam rich, and ever so slightly bohemian. Stunning with a light coloured strappy sandal.

I don’t have an earthy or bohemian edge to my style, but I thoroughly enjoy dressing my clients who do. Some like to wear boho in large doses, and others like to incorporate touches here and there. Do you have a bohemian element to your look?

People often ask about my outfit creation process so I have been trying to break it down into a set of useful guidelines. This has actually been quite difficult because I don’t think about outfit creation in a structured way. The whole thing is very intuitive and quite chaotic. But having thought about it for a while I realize that there are definite steps along the way. 

One of the common ways that outfit creation starts is with a single item. Often one of my clients will show me an item they purchased that tickled their fancy, but that they are struggling to incorporate into outfits. So together we get down to business and come up with ways to wear the item to ensure that it deserves a spot in my client’s closet. 

I’m going to use the example of a client that bought the striped seersucker trousers on the right. In less than an hour we went through these steps to arrive at several outfits. 

Assess Fit to Set the Scene

My client tried on the trousers to ensure they fit and looked fab. The fit was similar to that of the model in the picture, except that they were full length with extra leg scrunch. They fit exceptionally well on the bottom, waist, crotch point and thigh, which opened the door to many styling possibilities on top. My client would probably not have been comfortable wearing a tucked top with these trousers had they not fit as well. 

Their tapered hem widths made a range of heel heights a possibility. A wide hem width would have meant committing to a particular heel height in order to sport perfect pants lengths. Their semi-dressy vibe meant that we could dress the look up and down, for work and for play. This information set the outfit creation scene right from the start by influencing the types of items we chose to match with the trousers. 

Keep Troubleshooting Tactics Top of Mind

Throughout the process of combining tops, toppers, footwear and accessories with the trousers, we have three questions top of mind to troubleshoot the combinations that don’t look quite right. 

1. Is it the length of the tops, toppers and trousers causing unflattering proportions? 
2. Is the contrast between the items and between the items and your skin tone too high or too low? 
3. Will the outfit look better with heels? 

I sometimes ensure that we keep these things top of mind by mentioning them to my client at this point in the process. 

Select an Assortment of Tops

The next step is to pull all the tops that might work from my client’s closet and lay them out on the bed with the trousers. As I selected tops from her closet I was thinking about her needs: her comfort zone, how to evolve her look, how to incorporate current trends into the outfits, how the outfit reflects her style descriptor, and the settings in which she’ll be able to wear these outfits.  

Because the blue and white pinstriped trousers are a Summery neutral, we selected tops in neutrals like white, grey and navy, and in colours like green, coral, brown and red. We pulled styles in Summery weights like cotton-rich and silky fabrications, both in knits and wovens, to match the weight of the bottoms. We had an assortment of solids and the odd pattern for a pattern mixed effect. The top silhouettes ranged from formfitting to oversized, long sleeved to sleeveless, blousy to T-shirty, and from high necked to scoop.

As I was pulling out the tops, my client thought some of the tops had great potential, but was unsure about the rest. Perfect! It’s part of my job to gently nudge clients out of their comfort zone by introducing them to new ways of wearing items that might evolve their style. That way their style will feel refreshed, which is part of the reason they asked for my help in the first place. Let the experimentation begin.

Depending on the style of the top, we tried the tops tucked, faux tucked, semi-tucked, and untucked, using the belt that came with the trousers. We scrunched sleeves and added layering camisoles when necessary. With troubleshooting questions top of mind we kept on fiddling with the outfit until the proportions were flattering. 

We scratched the combinations that were “okay”, and stuck with the tops we liked most with the trousers. They covered an assortment of silhouettes, colours, patterns and fabrications because my client had a lot to work with. You might not have as much to work with, which is fine. But you’re good if you have at least three tops that will work with the trousers. 

IMPORTANT: There is no way we would have been able to accurately assess which tops would look best without physically trying them on with the trousers. Looking at the ensemble on the bed is NOT good enough. You must try on the complete combination in front of a full-length mirror to check whether it’s to your satisfaction. 

Introduce the Optional Topper

A topper, either a cardigan or jacket, is not essential to the outfit but a great option in cooler weather or arctic air conditioning. Again, as I went back to the closet to select topper options, I was once again thinking about her needs. She wants to venture into the world of jackets because they look more polished, but she likes the comfort of cardigans and needs more casual options. So out came a cropped navy cardigan, a tailored navy blazer with plaid trim, a blue denim jacket, and a grey blazer with white piping. 

We continued to experiment by throwing the toppers over all the top and trouser combinations. Eventually, all four toppers worked over the trousers with the right top. For example, an untucked and oversized silky navy high-low blouse looked great with an open cropped navy cardigan. A tucked white layering knit top was fab with the dove grey blazer because the white of the top picked up the white piping and buttons of the blazer. The denim jacket looked great over most of the tops, both tucked and untucked. The navy blazer with plaid trim made a delightful preppy and fashion forward statement because it added another pattern into the mix. We scrunched sleeves, turned back cuffs to showcase the striped lining of the grey blazer to add even more pizzazz to the look. We also frequently changed up the outfit by simply swapping out the topper while the rest stayed the same.

I kept on “reaching” for an imaginary light coloured topper in a shade of white to complement some of the outfit combinations. We recognized that this was a wardrobe gap and promptly wrote down the item onto the next shopping list. 

My client then tried on all the toppers with our favourite top and trouser combinations and looked at the outfits in her full-length mirror. Once again, there is no getting around this step.

Ground the Outfit with Footwear

An outfit might not need accessories, but it always needs footwear. The tapered hems of the trousers meant we could match them with any heel height. So we pulled out dressy nude wedged pumps, casual white peep-toe flats, taupe booties, and tan sandals. We made sure that the assortment of footwear could dress the outfit up or down. We paid particular attention to how the colours of the footwear harmonized with my client’s hair and complexion. She has gorgeous brown hair with red tints, so any light or dark brown shade of shoe picked up the colours in her hair and matched the belt, creating instant harmony. Of course, as we applied the troubleshooting questions to the outfit, the light brown and taupe footwear looked particularly fab because it created a low contrast against the pattern of the trousers. 

Further troubleshooting the outfit, we noted that some top and bottom combinations looked better with heels than with flats. For example, longer tops worn untucked over the trousers looked best with the heeled wedges to balance out proportions. Flats and low heels were more elongating when they created a low contrast against the pattern of the trousers. We also frequently changed up the outfit by simply swapping out the footwear while the rest stayed the same.

By the end of this process my client had tried all the footwear options with all the potential outfits and evaluated them in front of her full-length mirror.

Finish off with Accessories

Although I am outlining this process as a set of steps, it is seldom as ordered as this in practice. Although accessories are the last main area to address, in reality we are normally trying them on throughout the process as we get inspired.

My client does not like to swap out her bags so we ensured that all of the outfits worked with her neutral taupe bag. We also kept the belt the same because it was the only one we had to work with. I did suggest a taupe belt and white belt to match the shoes as a way of subtly changing up the look, and adding cohesion to the outfit. The belts were added to the shopping list. 

We wrapped a few scarves over some of the outfit combinations with and without the toppers. In some instances the patterned scarves added extra pizzazz as they picked up the blue/green tones of my client’s eyes. Sometimes the scarves created a fun pattern mixed effect, which was out of my client’s comfort zone. But I suggested that she be a devil and try the look on a day when she’s feeling brave. And often we preferred the outfit without a scarf. 

Evaluating the Outfit Shortlist

I mentioned my client’s needs several times above, and it is worthwhile to revisit those needs one more time with the final set of outfits. In particular, I make a point of thinking about when and where my client will actually be wearing the outfits we have created. After all, there is no sense in creating outfits for an imaginary lifestyle.

For my client above, the versions with the denim jacket were more casual and appropriate for Casual Fridays or casual weekend errands and evenings out. The ones with the navy cardigan were for relaxed non-denim days at the office, while the versions with the tailored blazers were for workdays when extra polish was required.

Then there is the all important happiness factor. Throughout the process we have been thinking analytically about fit and style descriptors and settings and many other factors as we decide which of the flattering combinations are best. But ultimately the thing that makes a good outfit goes beyond that into emotional territory. So during the process, and particularly at the end, I ask my client questions to get at how happy she feels in the outfit. Does it feel a dash fussy and uncomfortable? Do you feel fit and healthy in this outfit? Does it make you feel interesting and attractive? Does it make you feel dumpy and boring?

Of course, sometimes you need to push the boundaries of your comfort zone and violate your happiness factor to experiment with something new. The important thing is that you do this consciously. Let an outfit through if you know how it is testing your comfort zone, but never let one through if there is a nagging doubt that something isn’t quite right.

After we assembled about twenty-five outfits in front of the mirror, it was easy for us to identify the combinations that were the best of the best. So we documented those, as well as the few that were a little outside of my client’s comfort zone, just to have those options too.

Taking it on the Road

You can only take outfit evaluation so far at home in front of a mirror. You need to road test the outfits in motion, in real weather, and in the intended setting. Putting an outfit through its paces is always the best and final way of evaluating it. But being satisfied with what you put together at home has given the outfit a successful start.

I’ve repeated this outfit a few times this Spring because the tartan trousers are a wardrobe favourite. Also, I can run errands wearing high-top sneakers in the morning, but change into pumps when seeing a client in the afternoon while keeping the rest of the outfit the same. And change straight back into sneakers in the evening for a casual dinner out in our neighbourhood, which means walking up a steep hill from our house. This outfit is flexible, comfortable, and ready for action. 

I’ve had the tartan skinnies for a while — I debuted them at Fashion Week last year. I wear them year round because they are surprisingly versatile and a great weight. Another huge thank you to Greg for insisting that I keep them when I had my reservations the first time I popped them on. Now I can’t imagine my wardrobe without bright tartan bottoms. Although I’ve worn them with a denim shirt and coloured tops, I like these pants best with either a black or white top. So that’s how I’m sticking to wearing them from now on. 

I tried ever so hard to make the on trend sassy sweatshirt work for my style because I really like the concept. But it was a no-go. I felt like I was wearing pajamas no matter how I sliced and diced it because I don’t wear T-shirt or fleece fabrications unless I’m getting ready for bed. So although I’ve helped several clients choose their sassy sweatshirts, I had to move on to my substitute for the trend. A casual crew neck, chunky cotton knit pullover with welts did the trick, and I am so much happier sporting this item as “my sweatshirt”. It’s from Banana Republic’s Monogram collection and was only available in brick and mortar stores. I was drawn to it immediately because with the addition of huge shoulder pads it would be just like an item I wore to death in the ’80s. And nostalgic pieces make me happy. 

As with most of my welted pullovers at the moment, I faux tuck the welt to reveal a portion of my belt. In this case I’m wearing a white belt to create a low contrast with the top and match the shoes. I’ve heard the guideline that you shouldn’t wear more than two pieces of the same colour in one outfit. Perhaps that was meant for non-neutrals? Some outfits do look better when a colour is repeated twice or less. But neutrals are different somehow, or at least I choose to think so.

We need to wear toppers in May because, aside from the occasional gorgeously warm day, most Seattle Spring days are quite chilly. I chose a denim jacket because it’s less harsh than the black I often wear with these pants. This particular denim jacket is twelve years old and I’ve had it completely altered to fit in a tailored fashion. It’s not going to date and I am never passing it onto another home. I like the sleeves left long as well as scrunched. 

As I mentioned at the beginning, I matched the outfit with white pointy toe pumps to dress up the look for a casual appointment with clients, and with white high-tops to dress down the look for errands and a casual dinner out. These new white pumps are wardrobe workhorses, and I can’t believe I managed without them because they work with so much of my wardrobe. Who knew white pumps would be so versatile. 

I finished off the outfit with an old sporty hobo, silver watch, wedding ring, and geek-chic specs. I am very unsporty and bat for Team Dressy, so I’ve surprised myself at how much I’m enjoying wearing aspects of the Sporty Trend. As long as I mix these sporty pieces with dressy items and classics in one outfit, I feel right at home.