Most of my clients, who represent all age groups, have added boyfriend jeans to their wardrobes as a roomy alternative to skinnies, straight legs and boot cuts. Some wear them baggy and slouchy, while others prefer them a lot more streamlined. How you’d like your boyfriends to fit is of course completely up to you. 

The styles below have been winners with my clients, and I wear three of these options myself. Most of the styles are cropped and rolled well above the ankle, but some are full length.

• KUT from the Kloth Catherine Slim Boyfriend Jeans: These have been absolute winners across the board in terms of price, fit, quality and length. No tears, holes and hectic distressing. The denim is pretty thick and the fit around the hips and seat flattering. It’s been extremely interesting to see them work well on curvy and straight body types. Also available in white, a lighter wash and plus sizes. I have these in white and sized up for a baggier fit. 
• Gap Sexy Boyfriend: These tend to be baggier than the Catherines, wider on the waist, and longer in the rise. I also have these, wear them both rolled and unrolled, but prefer the fit of the Catherines from KUT. 
• True Religion Cameron Boyfriend in Defiance: These are gorgeous, full length, and very comfortable. But you have to make peace with the bulky back pocket flaps, and distressing. Runs true to size, but size down if you want them to fit in a less baggy manner.
• True Religion Brianna Slim Boyfriend in Granite: They are a narrower cut than the Camerons and a lot more distressed. They also don’t have the bulky back pocket flap. 
• True Religion Cameron Boyfriend in Pioneer: I have these and am thrilled with them. They are 100% cotton, which is rare in denim these days. The lack of stretch gives them a crisper feeling, and their full length piqued my interest right from the start. I wear mine baggier than on the model and bought them in my regular size. I adore the bulky back pockets and always tuck in a top and wear a belt to showcase their cheeky effect. 
• Ann Taylor Loft: These are super soft and run a little big. Comfy on the waist and hip. Also available in cream. 
• Old Navy Skinny Boyfriend: Some prefer the fit of these over the ones from the Gap and Loft because they are more streamlined. The price is especially appealing for a casual, kicking-around, style.

Some of my clients have created a similar boyfriend jeans vibe by sizing up on straight leg jeans and rolling up the hems. Either way, the styles that expose part of the lower leg are perfect on days when it’s too cold to wear shorts but too warm for jeans.

For my Mother’s Day post you saw me wear a flared midi skirt with a roomy crew neck pullover and unzipped bomber jacket. I finished off the outfit with white pointy toe pumps, white clutch and style constants, my gold watch and wedding ring.

Here I swapped out the skirt for a pair of full length boyfriend jeans and added a white belt to prevent them from falling down. By swapping out my bottoms, I’ve completely changed the vibe and look of the outfit. The former was dressy, modern-retro, ladylike and quite classic, while the second is casual, trendy and slightly tomboy.

Swapping out my skirt for a pair of jeans is an outfit creation strategy I use regularly when sporting a look from day to night. For example, I might be wearing a skirt during the day because I’m wearing business casual to work with clients. But will change into a pair of jeans while keeping everything else about the outfit exactly the same when heading out for a relaxed bite to eat later in the evening. I also find jeans a lot warmer than wearing a skirt with nude hose, which keeps me toasty when it cools down at night. 

The jeans are True Religion’s Cameron Boyfriend in Pioneer, and I LOVE them because they are full length and baggy. It’s hard to find a pair of boyfriend jeans that are long enough to roll once at the hems to create a cuff. Most boyfriend jeans are cropped above the ankle and rolled further up the calf and therefore too short to create this silhouette. 

I usually wear these jeans lower on the hip and on a looser belt hole than this so that the crotch point hangs down further to create a slouchier effect. Wearing roomy jeans low on the hip makes them baggy on my bottom and creates “saggy-butt”. But in this case the jeans don’t sag at the rear because I’ve fastened the belt tighter on the waist, which lifts the crotch point and makes for a more snug fit around my buns. Next time I’ll feature them with saggy-butt because that’s how I wear them more frequently. I fully support the Slouchy Movement. 

The bulky patch pockets with flaps mean that I always tuck in my top and add a belt when wearing these jeans. It makes them less versatile I guess, but I tuck my tops and add a belt to jeans and trousers very frequently anyway, so that doesn’t feel like too much of a restriction. Plus I like the pockets! They look cheeky to my eye. I can faux tuck the pullover above the belt because it has a banded bottom.

Although more tomboy than the skirt version, the white pointy pumps, lace, and shocking pink cashmere pullover are pretty elements that add the ladylike factor back into the outfit. Although my style is equal parts Ladylike and Androgynous, I want to step up the ladylike aspect of my style this year because things have been feeling a little too tomboy. Wearing pointy toe pumps has been one way of achieving my new style goal.

Roomy, arty dressing with lots of drape is a hit with some of my clients because it’s comfortable, feminine, interesting and breezy. We add structured sandals and often a structured bag to the outfit for extra polish. The pieces below are one way to create an arty and drapey ensemble. 

• Eileen Fisher Cowl Neck Dress: A knitted dress that’s weighty enough to not cling against the body. It’s quite genius! Structured in all the right places, machine washable, flattering, and pretty timeless. Great length, available in seven colours, and in plus sizes. 

• Nic & Zoe Four Way Cardigan: These lightweight gauzy linen-viscose cover-ups have been a hit with my clients who are sick of wearing classic cardigans, boyfriend cardigans, cascading cardigans, or don’t want to wear jackets. Fabulous over sleeveless frocks. Pick a fun colour to go over the cowl neck dress. Nic & Zoe’s Caliente Bahama bolero is another cover-up option.

• Blondo Malaika Sandal: Finish off the outfit with comfy high-vamped sandals. The taupe looks particularly Summer-y. Read the rave reviews. 

• Blondo Opaline Strappy Sandal: Try this option for a lower heel and slightly daintier vibe. Comfortable, stable and soft. 

• Botkier Calie Crossbody Bag: This distressed metallic darling doubles as a clutch when you want to give the straps a break. I like the juxtaposition of the angular bag with the soft drape of the dress and cardigan.

If cardigans aren’t your thing, try a denim jacket, denim vest or bomber over the top of the dress. Or bare your arms, add a sunhat, and you’re good to go.

Understanding my client’s needs is a crucial part of making our time together successful. For new clients this means filling out a questionnaire which is complemented with an extensive chat in person or over the phone. And with regular clients I have a pretty good idea of their outfit needs already, although we frequently re-address them to make sure we are still on the same wavelength.

Style needs include style goals and many other factors. They include internal factors, like style preferences, style persona, and figure flattering priorities, and external factors like lifestyle, climate and environment. Perhaps you have already dedicated some time to understanding your needs, or maybe it has been happening organically over time as you evolve your style. Either way, understanding your style needs can really help you to create outfits that make you feel fabulous.

When I thought about how to articulate in a blog post how I actually use knowledge of my client’s style needs during outfit creation sessions, I realized that I keep five things top of mind. These things form a frame of reference that I refer to before we select one of the four approaches to outfit creation. I also refer to them while we’re creating outfits, pulling items from her closet and laying them out on her bed. And I refer to them again after my client has fitted on an outfit as part of the outfit evaluation process. 

You might use these same five things as a kind of “cheat sheet” during your own outfit creation, thereby helping you to focus on and attain your style goals. 

Comfort Zone

Everyone has a comfort zone. You need to make sure that your outfits aren’t so far outside this comfort zone that you don’t want to wear them. For example, I have one client who is game to wear skirts and dresses to her casual work environment, as long as she’s wearing casual or flat footwear. But matching her skirts and dresses with fancy high heeled pumps or sandals makes her feel prissy and too dressed up, and takes the outfit too far outside her comfort zone. 

Evolution 

This is a counter balance to the previous point. Some of your outfits should push the boundaries of your comfort zone in order to evolve your style and prevent you from getting stuck in a rut. Many clients have asked for my help because they want to refresh their style, which means taking them out of their comfort zone to some extent. So I’m always gently encouraging clients to try new-to-them combinations, but with enough “comfort zone” elements to ensure that they feel confident in the outfit. For example, I suggested to the client I mentioned above that she wear skirts and dresses to work with a dressy wedge sandal. Dressy enough to push the boundaries, but casual enough that she will be comfortable. 

Trends

I believe that a stylish outfit incorporates a bit of “now”. This means being aware of fashion trends and choosing ones that you can adopt. Remember that trends do not change every year and needn’t be hot off the press directional fashion. Including that all important now-factor could mean incorporating a five year old trend. For example, instead of wearing a tailored tucked button-down shirt with a pencil skirt and round toe mary jane pumps, I suggested to my client that she match the same skirt with a less structured untucked top like a soft silky tee and high vamped wedge sandals. That’s because unstructured structure and high vamped footwear is on trend. 

Style Descriptor

Your outfit should map back to your style goals, style descriptor, or the set of adjectives that you’ve compiled to describe the style you are aspiring to. For example, my client aspires to looking feminine, professional, modern, modest and interesting. So we took the same pencil skirt that we matched with a soft silky tee and high vamped wedge sandals, and added a playful pendant necklace, a clutch handbag and a broad cuff bracelet.  

Setting

Every outfit should map back to a setting in your lifestyle, be it for work, play or a special occasion. There is no point in creating dozens of killer outfits for an imaginary lifestyle! With my clients we try to get quite specific when describing the setting (or settings) that map to an outfit. It could be a cocktail party, a normal day at the office, presentation day at the office, a weekend stroll down to the farmer’s market, spending time in the park with the kids, a BBQ at a friend’s house, or casual dinner out.

Understanding one’s needs is sometimes easier than using that information to make decisions. A simple cheat sheet like the one above can make it easier and ensure that nothing is overlooked. Of course there are other criteria to consider, like the all important happiness-factor that is crucial to evaluating the overall success of an outfit. And there is only so much evaluation that you can do in your dressing room, so the road test is equally important. I’ll be covering these aspects in future posts.