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  1. Megan M Avatar

    Hello Mary,

    I love you blog. What is your opinion on how short dresses/skirts can go at the workplace? Does wearing opaque tights with a skirt/dress make a difference in terms of how far you can go with length?

    Thank you!

    1. Mary Orton Avatar

      Hi Megan! I think opaque tights *help* but still don’t make short skirts OK in the workplace — especially in conservative ones. As you can see on my blog, I never go more than three inches above the knee. That’s the rule of thumb I recommend!

  2. Kimberly Turner Avatar

    Hi Mary!

    Just a quick note to say I love your style. Thanks for all of the great tips! I look forward to reading your blog, receiving your newsletter and to all of your ideas and recommendations on fashion and style!

  3. Nikki Avatar

    Hi Mary

    I LOVE your blog. Thanks so much for sharing your style and for taking the time to post tips on where we can find similar items.

    Is there any chance you could do a wardrobe organisation post? I’ve always struggled to optimise how to find what I need to pull together creative looks when rushed in the morning so I inevitably just wear ‘easy’ outfits.

    Looking forward to hearing from you.

    Thanks and merry Christmas!

  4. Stephanie Avatar

    I’m recently transitioning from a very casual nonprofit job to a high end hospitality firm, and I just know your blog is going to be lifesaver for putting together my new wardrobe. I have some basics butam looking for a good, structured, slimming blazer – and I’m stumped. Where would you recommend? Thanks- happy holidays!

  5. Mary Avatar


    I’m hoping for your advice about what to wear during *really* cold weather. I’m starting a new job in Chicago in January that requires business attire every day. I’d like to wear a lot of dresses, but I’m wondering what kind of tights/nylons to wear with them? Is wearing nude nylons ok? I’d like to avoid wearing opaque tights with my black dresses.


  6. chris juneau Avatar

    When will we see you in Black Hawks gear? Frankly, it’s the only couture that will do you justice. Thanks, Chris Juneau

  7. Kristine Avatar

    Hi Mary,

    As a new graduate, I was thrown straight into corporate finance and your blog is EXACTLY what I needed to help me figure out how to be professional without being stuffy. I absolutely love it!

    A quick question though – I’m going on a business trip next week and during the day I’ll be wearing business formal, but I’m also invited to a cocktail event and a dinner (at a high-end restaurant). I’m the only female going and my male colleagues will not be changing to go to these events, so should I wear my outfit from the day (more likely suit skirt/trousers with silk blouse) to the event, should I change into a dress that is office appropriate but wouldn’t necessarily choose to wear to formal meetings with clients (but is fitting in a cocktail/dinner environment), or should I wear the dress during the day also and not change?

    As you point out yourself, there are often very few female role-models in corporate jobs and sometimes it’s difficult to get the nuances just right when it comes to appearance, but you’re doing a wonderful job of providing the guidance and inspiration to “Classy” ladies everywhere!

    Thank you in advance.

    All the best,


    1. Sacha Irving Avatar


      Completely understand the struggle your facing as Ive faced the same issues in investment banking. From experience people generally change attire for evening drinks if you have time to go back to the hotel room before. A dress is good for both occasions, but recommend changing regardless.


    2. Mary Orton Avatar

      Hi Kristine, I’d actually recommend not changing. From my experience in many, many situations exactly as you described (only female, business formal, evening event afterwards) it’s better to stay professional throughout. If you change, it can draw unwanted attention and even suggest that maybe you see the evening events as a date-type setting that requires a wardrobe change, instead of a continuation of your job. If your male colleagues aren’t changing, you probably shouldn’t either, in my opinion. However, I would say that you could definitely get away with a hybrid of the two! Wear a dark suit that features a matching jacket and dress… perhaps with a scarf. At the evening event, it’ll seem very natural for you to ditch the suit jacket and scarf on the back of your chair, and now all of a sudden you’re in a sleek black dress. Win-win!

  8. Cara Avatar

    Hi Mary! I love your blog, especially your posts about office holiday gifts. I’m hoping you could do something similar regarding retirement gifts. My boss is about to retire and, as you can imagine, she has just about everything. I’d love to get her a gift that shows how much I value and appreciate her mentorship and friendship, but I haven’t been inspired yet.

  9. Kathy Avatar

    Hi Mary,
    I just read another blogger posting about “A Day in The Life Of…” and though immediately that is something you should do. Oh, how I’d love to follow you around for a day. How do you choose your clothes? How do you shop? Do you have a personal shopper at you favorite stores who calls to let you in on things as they first arrive, or do you just show up and start digging through the racks? Do you have other people who work with you? How do you decide whether to do the shoot in SF or NYC? How did you fit everything in when you were still working in the financial world? Do people recognize you off-duty? Do you have to line up sponsors or do they contact you? Have you ever thought of expanding into lifestyle posts? Gosh, I sound a little like a stalker, don’t I? Anyway, hope you give a post like I suggest some thought. I bet I’m not the only one who would love to read about your endeavors.’
    Best wishes for a highly successful new year, and thanks for keeping things classy!

    Thanks for your site

  10. Mayte Avatar

    Hi Mary! I Love your blog. Please can you tell me where did you buy the white and black jumper that you wore at the airport.
    Thank you very much.

    1. Mary Orton Avatar

      Hi Mayte! It’s from J. Crew but is about 3 years old. Maybe keep an eye out on ebay for it! : )

  11. Kathy Avatar

    I totally get why you currently prefer the sunny west coast to the snowy east, but it would really be cool (pardon the pun) if you did an all-out winter styling session for dealing with brutal cold and deep snow. Did you maybe do some when you went skiing?

    1. Mary Orton Avatar

      Great idea! I wish I had, but was focused on the slopes : ) I’ll keep that in mind and try to provide some more cold weather styling tips!

  12. Debbie Avatar

    Classy style Mary…love it! Quite a while ago you wore a pearl like adornment on the color of a button down blouse. It appeared to be like collar jewelry, for lack of better description. It has stuck with me and reminds me of the tie-back jewelry used in the 80’s on over-sized shirts.
    Wondering where you got it. It really dressed up the blouse.

  13. Rachael Avatar

    Hi Mary,

    Can you do a post on sales call attire. I find it hard to dress for these, as you have to be able to travel relatively easily, you can’t look disheveled during your pitch, and you want to balance both office “vibes” with your outfit. For example, I work for a start up (creative)…but it’s in the healthcare industry (conservative). Any advice you have would be great!



  14. Laura Avatar

    Hi, just had a quick sizing question β€” can I ask what size your Brooks Brothers camel hair blazer is, and also what size you usually take from J. Crew? I’m considering buying this blazer (the patch-pocket one, from an online reseller) but unsure of how it fits, and the fit it has on you is exactly what I’m looking for. Thanks!

    1. Mary Orton Avatar

      Of course, although I don’t know if you’re bigger/smaller/taller/shorter than I am, so I’m not sure how much it will help! But for what it’s worth, I’m 5’10” so in Brooks Brothers blazers I’m a Size 4 for sleeve length and a Size 2 in general from Brooks Brothers and J. Crew — though I go up to a 4 or a 6 in J. Crew blazers for sleeve length as well. Hope you love the blazer!!

  15. Sonia Avatar

    Hi Mary,

    I really love the black belt with a round gold buckle that you wear with many of jeans outfits–can you tell readers where to get it or something similar?

    Thank you!

  16. Kathy Avatar

    Thought you’d want to know that the Bloglovin feed on March 26, featuring the St. John’s classics isn’t showing up on the blog when I go directly to rather than through Bloglovin. Perhaps it was actually scheduled for the blog today and Bloglovin released it early? Just wanted you to know in case there is a technical glitch somewhere.

    1. Kathy Avatar

      Ah.. all seems ok now.

  17. Emily C Avatar

    Hi Mary! Love the blog and I’m a big fan.

    Question for you – what are the best sources for well-made women’s suits? Looking for something well made and well tailored at or around $1,000. I work in a conservative office, and all of the men are able to get custom suits made for around $800, but I haven’t found anything as custom or as nice for women! Would love any tips that you have


  18. Alyson Avatar

    Hi Mary,
    I was wondering your thoughts on tights. I have been told that buff tights to blend in with your skin tone are a necessity when wearing skirts and dresses in the workplace, but I have also heard that they are not necessary at all. Another thing I have heard is that if you do wear tights, you should match them to your shoes. I have no idea what advice I should take. What do you think?

    I am just getting a start with my profession so I don’t have a lot of practice creating classy but original work outfits. Your blog has been really helpful so far!

  19. Rosanna Tuite Avatar

    Hi Mary,

    Just wondering if you have heard of the Bicester outlet in Oxfordshire, it has to one of the best in the world. I am hoping to get back there real soon.



    Ps. Love your blog, I check into it everyday.

  20. Kathy Avatar

    Technical glitch on today’s Memorandum “View the Post” link. Says page not available. Trying to access on my laptop w/o success.

    1. Kathy Avatar

      Fixed now.

  21. Kathy Avatar

    Hi Mary,
    Since I’m living in the last century without a smartphone, I don’t think I can access your snapchat postings. So I’m wondering if there will be another way to view those posts. Another blog perhaps? (Hint, hint).

  22. Kelsey Reaves Avatar

    Hi there!

    I really love your website, Memorandum, and was wondering if you ever have guest contributors? I work for and we would love to write something πŸ™‚ Over the past few months, we’ve written for The Huffington Post and and I think we can provide some pretty awesome content for your readers.

    Here are a few samples of our writing:
    Maximizing Your Closet Space (
    Creative Ways to Display Your Makeup (
    Looking forward to working with you!

    Kind regards,


  23. Kathi Avatar

    Hello Mary,

    first of all your blog is what I was looking for since I started as a professional in banking industry facing everydays challenges how to dress at work in an adequat and non boring way. I love your inspirations and advices. Btw advice: how many colors are the max to have in one business outfit in order not to look like a clown? πŸ˜‰

    Thanks in advance.

    All the best,

  24. Kathy Avatar

    I’ve been wondering about what type of bra you recommend when wearing something with spaghetti or narrow straps. I hate the exposed bra strap look and wonder if you go with a strapless bra or do you use the double sided sticky tape to adhere strap to strap?


  25. Caitlin Boss Avatar

    Hi Mary,

    I came across your website the other day because my fiance and I and going on safari and then to Mauritius for our honeymoon next year and I have been trying to figure out what we will need to purchase for the safari part. I have already used your blog to help me with my office fashion. My norm used to be slacks and a button down….that’s right just like a dude because I didn’t know what else was appropriate. Thank you so much for telling me through this blog that I can wear other things! Anyway, I saw that you did a post for your honeymoon portion in the Seychelles and was wondering if you planned on doing something similar for the safari or if you can give me any pointers as to where to buy stuff. Thank you so much again!


    1. Mary Orton Avatar

      Hi Caitlin, Thank you!! Yes, I’ll be doing a full honeymoon post in the coming weeks, so stay tuned!

  26. Ed Bathen Avatar

    Mary, I am in the process of starting a new company, Compass LED Solutions dealing in LED lighting for all situations…commercial, industrial and residential. My lady says you once published an article about how to start a blog.
    Could I get that material sent to me so that I might figure out how, when and where to get a better feel for this media.

    Thank you,

    Ed Bathen

    1. Mary Orton Avatar

      Hi Ed, I’m sorry, she must have me confused with another blogger. I don’t think I’ve ever published anything about how to start a blog, but will keep that in mind for future content! Best of luck with your company!

  27. Kathy Avatar

    Hi again Mary.
    I noticed you have changed your home page headings a little to include “Lifestyle”. I wonder if under that category you have ever considered expanding into dΓ©cor? Little things such as your copper Moscow Mule mugs, and the tray you featured in your Holiday Memo Gift Guide, and the dining table you had on Instagram are all things I’m thinking of. Please give it some consideration.

    Kathy Edens

  28. Maggie Avatar

    Hi Mary,

    Finally a lovely, modern fashion guru with timeless looks! I adore the looks you share and find them so applicable to my 9 to 5 in the Financial District of NYC. As of late, I’ve been struggling with heel and height etiquette in terms of my superiors.

    You see… I work with many men around my height (5′ 9″) while my manager is only 5′ 5″ or so… The troubles are caught between my desire to look kick ass and polished in heels,while not wanting to literally belittle my manager. This also comes on the heels (no pun intended) of being newly hired and quite young.

    Do I skip the heels to not feel so domineering or do I accept the freedom to tower at 6′ around the office?


  29. Allison Avatar

    2015: A Retrospective – the link to the second photo does not work, can you resend or let me know where the black and white blazer is from?

    1. Mary Orton Avatar

      Sorry about that, just updated it! You can also check out the post here:

    2. Mary Orton Avatar

      The link has been updated, so it should take you directly the right spot now!

  30. Samantha Avatar

    Hi Mary! Love your blog! Your looks are so creatively classy and inspiring!

    My office is very casual, which is so nice. Sometimes I dress up, but a lot of times I wear jeans and a cute blouse. A lot of my wardrobe doubles as work clothing and dinner/drinks/casual Saturday clothing.

    Today I need your help with shoes. I am seriously struggling! It seems every pair of shoes I buy cuts and blisters my feet. Both heels and flats alike. I am 5’9″ already, so all I want is a little black kitten heel (2″ max) and a good pair of pointy toe flats. I try shoes on in the store and they feel fine (trust me I do a good walk around the store). But the first time I wear them, I can barely stand the pain. Some times I can break the shoe in and sometimes not. I have tried all the tricks (band-aids, moleskin, friction block). So Frustrating! I feel like my true size is a 7 3/4.. the 7 1/2 is usually too snug and dig in, but an 8 can be too loose and slip.

    So far I have bought middle of the road brands like Cole Haan, J Crew, Clarks with no luck. I am wasting so much money! I have my eye on a gorgeous pair of Manolo Blahnik suede kitten heels but do not want to pay the high price tag if the same thing is going to happen. I tried on Stuart Weitzman, but they felt worse than anything I have tried yet!

    Do you have a secret? Do you think these high end names will be better for me? With shoes, is it better to be too snug or slip a little?

    Your help is really appreciated!

    1. Mary Orton Avatar

      Hi Samantha! I’m not sure I have great advice to offer, because I’ve personally had great luck with all of the shoe brands that you mentioned (Cole Haan, J. Crew, Stuart Weitzman, etc.). I have a relatively narrow foot and am a true 8.5, so don’t run into the same issues as friends of mine that fall between sizes like you and/or have wide feet (not sure if this is true for you or not). In general, I would say that there is indeed a reason high end shoes are… high end. From my experience, Manolo Blahnik, Jimmy Choo, Christian Louboutin demand those high price tags because they have superior construction and are made from the very best leather out there — leather that molds to your foot better than more affordable options. Since it sounds like you’ve exhausted all other options, it might be worth a try splurging for a pair of Manolos. Otherwise, since you’ve tried all the band-aid, moleskin, etc. tricks, the only other thing I can think of is to continue buying the shoes that are a tad small (7 1/2) and try taking those shoes to a cobbler for them to be stretched in the places that typically rub before you wear them for the first time. I’ve had this done before and it’s awesome. They’re able to loosen up the places that are stiff and rubbing so you don’t have to go through the pain. Hope you find something that works!!

  31. Kelly Avatar

    Hi Mary–Love your blog! I was wondering if you color your hair? If you do, did you have a favorite colorist when you lived in New York City? I’m looking for one in NYC!

  32. Katie Swenson Avatar


    Love your blog. Creative and classy. I have to ask though, for a girl on a budget keeping fashion fresh can get pricey. How do you do it?

  33. Jocelyn Avatar

    Hi Mary! I love, love, love your blog!! I missed writing down your snaps the other day with all your books! I was hoping you could post them here. Also, do you have any recs on how to keep flats from getting worn out too soon? My flats seem to always get scratched and I don’t know if it’s me or just how flats are from normal wear and tear.

  34. Kaitlyn Rikkers Avatar

    hi good morning,

    I moved to San Francisco about a year ago from London and trying to step into some more west-coast fashion sense. I’ve been buying jewelry from this place: but don’t know of a local shop in SF where I may be able to find some things that are similar, less costly and with a greater variety.

    Thanks so much for your help in advance.

    All the best,

  35. Tamara Avatar

    Hi Mary,
    I’m curious how you maintain your designer shoes.
    Do you have a cobbler add a thin rubber lining to the bottom if the shoe has leather soles? or do you go “bare”?
    And which cobbler in SF would you recommend for such work if you have it done?
    I live in Reno and nobody here appreciates how delicate designer shoes are and tend treat them like hiking boots instead…. sigh.

  36. Hannah Avatar

    Hello Mary! I have been following you for quite some time and you are the one who has taught me classy style and office essentials! I am currently in college, and during these hot summer months I am taking summer classes. With that, I just landed an incredible job working for the Office of the President on campus. Do you have any advice for dressing business professional during sweltering temperatures while walking to class and attending the office?

    Thanks in advance!


  37. Mare Avatar

    Hello Mary!
    I have an off-duty style (date night) question for you – What is your opinion on purposefully shown under garments, such as a lace bralette or bodysuit? I have a wrap dress I absolutely love but is has a very deep V-neck. To avoid any showing any bar or too much cleavage I use boob tape and wear a plunge bra. It’s kind of a lot of work/stress. What do think of instead opting for a bralette or bodysuit and forgo trying to hide the bra at all? Do you think a late 20 something pull this off? Or should we leave the bralettes to a younger crowd?


    1. Mary Orton Avatar

      Hi Mare! For a date night, I think a bralette/bodysuit/lace cami is the perfect solution! It absolutely can be pulled off, and in my opinion, can even sometimes look better/more tasteful than the plunge bra option. Go for it, lady! : )

  38. liz Avatar

    Amazing site with some awesome content on fashion and lifestyl!

  39. Patia Storms Avatar

    Hi Mary,

    First of all, thank you for imparting your wisdom on us everyday! I truly enjoy reading your posts each week. Secondly, I know it may be out of your typical repertoire, but would you ever consider writing a post about your favorite books? I would love to hear about your choices of literature in all genres. Thanks!


  40. Rachel Avatar

    Hello Mary,

    I am a marketing professional in the IT industry and will speaking at a women’s conference soon (yikes!). I would love your advice on what you think is appropriate (yet edgy/memorable in the right way) to wear to something like this. I love the idea of a tailored jumpsuit with a blazer, or a crisp white shirt with well made leather pants.

    What do you think?


  41. Jessica Avatar

    Have you ever thought about doing an “Closet Tour” post? My closet always feels like a mess even when everything is up on hangers.. I’d love to see what your closet layout/shelving configuration is like and how you organize your clothes. Any advice would be much appreciated!

  42. Gina Rayson Avatar

    Hi Mary πŸ™‚

    I love the idea of wearing a jacket styled to be open and on the shoulders, but have a hard time determining fit. You do it so beautifully: are yours purchased to fit as if you will wear them traditionally, or do you size up/down based on your intent to wear on your shoulders?


    1. Mary Orton Avatar

      I always buy coats and jackets in my normal size, ensuring that they actually fit while wearing them. Personally, I don’t buy any coats or jackets with the sole purpose of wearing them over my shoulders, but always love having both options (to wear them fully on, or wear them like a cape). If you make sure the coat fits you properly (especially in the shoulders), it will fit comfortably when choosing to style it open, sans arms, over your shoulders, because that’s the place where it will hug and cling to your body. If you go too big, it will be falling off, if you go to small, it won’t layer comfortably over other pieces. In general, the style works best for coats or blazers that are meant to have that slightly “oversized” look. For super form-fitting tailored jackets, it’s not as easy, as they don’t flow over other pieces as nicely. Hope that makes sense!

  43. Alex Avatar

    I cannot wait to see your registry tips! This is the most challenging part of wedding planning so far. My fiance and I are pretty well established but we don’t have a full set of anything.

  44. Marian Avatar

    Hi Mary,

    Thanks for all of the great office wear tips! I love love your blog!
    I have an office etiquette question for you. I work in a midsize CPA firm in VA (a conservative field and semi-conservative market). I am most often client facing and must dress in business attire. My go to is a sleeveless dress and blazer. When is it appropriate to take off a blazer during a meeting with clients and partners of the firm? Today I was in a meeting with 3 prospects and was freaking hot but I was worried about taking off my jacket. My concern is that it would be unprofessional to take off the jacket in general and then to also reveal my unclothed arms would be wholly offensive and unforgivable. Maybe I have overthought this but your input would be greatly appreciated!

    1. Mary Orton Avatar

      That’s a tough one! It entirely depends on the setting, your colleagues and the prospective clients. If it’s a formal setting with everyone in business formal attire (jackets intact), then, unfortunately, you’re going to have to sweat it out. Of course, if you get so hot to the point of sweating profusely or feeling like you are going to faint, then by all means take the jacket off and just call it out–“Is anyone else particularly warm? Do you mind if I take my jacket off for a minute?” If this happens often, then I’d highly suggest investing in some suits where the dress has a short sleeve or elbow-length sleeve. That way, you can remove the jacket in the meeting without as much trepidation. Hope this helps!

  45. Nia Avatar

    Hi Mary

    Love your blog and check in every day.

    Just wondering how you deal with sunglasses and make up, I just cannot seem to get it right and end up with marks on my nose, so have resorted to hardly wearing them as it does not look great for a working day when your make is ruined before you even start. Like you have oily skin so primers, foundation and powder are all part of the daily routine.

    Please help, I know I am damaging my eyes by not wearing them.

  46. Caroline Avatar

    Hi Mary! I really liked your post about pink as a spring trend and the pressure you felt when you first started working to wear things that weren’t outwardly feminine. I am about to graduate college and took an Investment Banking job in NYC and have been worrying about how to find clothes that are stylish and make me feel good while still being professional (your blog has been a lifesaver)! Do you have any nail colors you suggest for a conservative office environment? I like to have color on my nails but realize that the fun colors I can get away with right now probably won’t go over so well in my new office. Thank you so much for you help!

  47. Suzanne Lewis Avatar

    My daughter lives in NYC and her husband was transferred to AZ. I live in California, run an Air Conditioning Company with my husband, I have always loved fashion and NYC. My daughters lease is up in a few months. I am thinking of coming to NYC to live for that time because I have always wanted to live in NYC and feel this is a good opportunity. I was doing some research and came across your blog. Wondering if I came if you would need any temporary assistance any time soon.

  48. Reeny Avatar

    Mary, I may have an issue. I purchased a black blazer on its own and cannot seem to match anything with it but jeans. It isn’t a formal suit blazer and can be worn casually. If I wanted to dress it up with black pants, how do I pick out a pair of pants that are the same black color and won’t clash? How do you make a blazer more formal when you didn’t buy it as a set?


  49. Sydney Avatar

    Hi Mary! I am in college and need a suit for mock trial. I want something nice, but not outrageously expensive, and it has to be very conservative (black/dark grey, no excessive embellishments), but I do not want to look frumpy. Do you have any suggestions for a skirt suit/ dress and blazer situation?


  50. Caitlyn Avatar

    I came across your blog recently and love it. However, I do find some of the pieces you feature to be expensive and out of my budget. I’d like propose a challenge (really, a blog series idea): Share work outfits, suitable for public sector and creative offices, that cost $200 or less. I certainly hope that this is doable, primarily because my job (working in marketing in the public sector) isn’t lucrative. Thanks, Mary!

  51. Havenly Avatar

    Hi Mary, I love your fashion sense. I’m looking to create a fashion blog of my own and have a few questions if you don’t mind. I was just wondering what wordpress plugins you use that shows the items in your post? Such as in this…
    How did you add photos of all of the jackets like that? And below it, what did you use to add “today’s outfit details” thumbnails? It’s really useful!
    Sorry, last question…
    what plugin did you use to show all the different dresses for each occasion ?
    Thanks so much if you can answer this, it would be a big help ! <3

  52. Christina H Avatar

    Hi Mary,

    Long-time fan here. A bunch of the girls in my office–and myself–have been following you for years, and we adore your sarcasm paired with your excellent work-wardrobe advice. We quote some of your quips when we are trying to explain our conservative dress to our new hires. What we really are missing and would love to see is a special edition discussing menswear in the office. Half of our fellas are very dapper, and the other half are missing the memo… pun intended.

    We would love to see yours and/or Rich’s thoughts on office dress for men. (we are conservative business casual in the office, and professional dress at client sites)

    Thank you,


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