A Quick-Fix Guide to Stylish Travel for Real Gals

I took a road trip with my husband a few days ago. Nothing fancy. He had some work to do in a few neighboring towns, and I went along with for the ride. A wee night away in a coastal town.. why not? And, despite the inclement weather (it is Scotland in February, after all), it was indeed quite a ride.

 on the way to Tighnabruich, Scotland

Why is it that you can never capture the depth of natural scenery on your digital camera? Or is that just me? But I digress.

As I was packing my overnight bag for the trip, I found myself reaching for the things in my closet that I have only recently come to understand are my go-tos. My anti-uniform uniform. The things that I wear in different situations that make me feel like me. Whether we are aware of it or not, all of us possess things we wear when we want to look cute, but not too cute as to be twee, and that look like you made an effort, but not, of course,  by trying too hard, all the while making a nod to the fact that you have a vague idea of who you are and what fashion is, but without looking like a victim of trends, but yet still working the occasional trend into your style and making it your own…..I think you get the idea. 

If you’re like me, your closet certainly has no shortage of stuff. You may, in fact, have the opposite of a shortage of stuff (a plethora? A deluge? Stuff coming out your ears?)  So really it is a matter of deciding upon which stuff works best for whatever you are embarking on. As one who has travelled extensively, both for work and for pleasure, I cannot stress enough the importance of making the most of one’s stuff when travelling. And so, with this sentiment in mind, the Highland Fashionista will now share with the universe, her favorite ways in which she likes to make use her stuff while travelling.

The colder climate (and possibly rainy) small-town break. Might as well start with something that is close to home (for me, anyway). These past few days, and well, every day if you live in a small Scottish town, I need something that is comfortable, that will go in and out of cars easily, and that isn’t too dressed-up, yet nice enough to go into a casual restaurant or pub. This was my look for my 2 day trip with my husband.

Skinny jeans by New Look
J Crew Perfect Fit Tee

J Crew Merino Cardigan in Taupe
Cropped Pea Coat by Guess

Clarks Asymmetric Ankle Booties

LL Bean Town and Field Tote
Links of London Silver Bracelet
Movado Watch

This is my go-to foundation wardrobe for, well, just about everything I do. My Being A Human Being Wardrobe. Skinny jeans, a long tank or tee with a more fitted or cropped cardigan layered over the top, and either heeled or flat, very walkable, short or tall boots. Cropped pea coat if it is cold, large leather tote bag, and simple accessories that you can wear every day. Maybe I’ll bring different accessories if the trip is longer than one or two days (but probably not). J. Crew makes lovely and durable thin merino and cashmere cardigans in amazing colors and prints, and I am well on my way to a very serious collection. I also like to add a pop of color from underneath by adding a fun tank or tee (try J Crew or H & M). You can literally go on a low-key 3-day weekend with one pair of jeans, one cardi, and three pairs of undies and tee shirts and feel quite comfortable doing so.  If you are going to be doing a lot of outdoor dodging about, and it is properly raining, I might exchange the pea coat for a lined trench with a hood. If I know that there may be a slightly more dressy night, add in a pair of heels or a lovely jacket and camisole.

The warm-climate casual beachy break. This is the one that gets people. Think about what you need. I mean, what you really need on a beach holiday. There are more people lugging HUGE suitcases for casual beach holidays than anywhere else I’ve ever travelled. The last time my husband and I went to the Canary Islands for some sun, this couple at the airport had bacon in their carry-on. Bacon. In their suitcase. Actual bacon. And although I would like to publicly thank that bacon-loving couple for the comic relief (Easy Jet from Prestwick to Fuerteventura in December! You know who you are!), I certainly hope that they did not meet with any unfortunate gastrointestinal illnesses from eating jet-fuel scented bacon that has spent an inordinate amount of time stuffed in a hot, cramped suitcase in the overhead compartment of a DC-9. But if they did, I suppose that is the universe telling us all that thou shalt not eat bacon that thou hast smuggled on Easy Jet. 

So....here are some (non-bacon) things that you do NOT need on a beach holiday: hair straighteners, (if there was ever a time to be natural, this is it!), green eyeshadow, fake lashes, acrylic nails, platform stilettos (think wedges and heeled sandals instead), or more than a few easy to manage pairs of shoes (including flip-flops!). You need sunscreen, lots of it. Bathing suits. At least two, more if your trip is longer than a week. For clothes, count how many nights you will be out and about and plan your outfits to that number, no more. Okay. Maybe one more, (sometimes it’s nice to have a backup), but no more than one. I tend to favor boho and preppy-inspired looks for warmer weather, depending on the vacation.  And finally, you will need bathing suit cover-ups. I like maxi dresses, because they are easy to wear, and you are instantly dressed. Properly dressed. You can go into a restaurant straight from the beach and look dressed.  You can also use them at night as well (hence lowering your outfit count in your suitcase), and layer one of your many J. Crew cardigans (or a boyfriend blazer, or a motorcycle jacket) over the top if it gets cold at night.

Thakoon Maxi Dress (from fall 2012 collection.....I pre-ordered this one...I just HAD to have it!)

I also favour tunic-style tops and shirt dresses.  Longer tunics can work as a cover-up, but they all look really cute and vacation-y with shorts or minis, or even over jeans with a pair of wedge sandals for casual evenings out. Shirt dresses are great for casual evenings, as they can be as casual or as dressed as your shoe choice (again, wedges and sandals people, wedges and sandals!),  and always look pulled-together.

LL Bean Signature Shirtdress

Michael Kors Tunic

And a note to all erstwhile beach goers of the universe! There is nothing worse than having to wait at a busy restaurant while looking at the backside someone in front of you who is either still half-naked and dripping wet, shirtless, barefoot, or any combination thereof. Again, nobody is expecting art, this is a beach holiday, after all. Just for goodness sake get dressed, people are eating! If you want to get all fancy, bring some kick-ass boho accessories to liven your look.

The warmer/cold climate city break.  Again, see aforementioned shirt dresses above for day in a warm climate. Comfy to wear, looks good on everyone. Layer-on tights, boots, cardigans, or a pullover to make it work for a colder climate. An awesome coat that will not slow you down is essential in cold weather. I tend to stick to traditional wool coats in interesting cuts or colors, as they translate from dressy to casual better than parkas or fur.

Your shoe choice will inform your level of dressiness. Walkable shoes are a must. Let me rephrase that…walkable shoes that are not running shoes, hiking boots, or the like are a must.

Check out Sofft, Aerosoles, and Bjorn, just to name a few. There are many places where, if you decide to nip in at the end of a day for the cocktail hour, you may be denied admittance if you are wearing sneakers. I know this seems old-fashioned, but it is true. It even happened to a friend of mine in Cleveland once. Cleveland...in Ohio... I know, right!?  It was just by virtue of the fact that the rest of us must have been displaying a more “acceptable”  footwear-to-fashion ratio that we were admitted despite her clearly very offensive sneakers…So. Leave the running shoes for the morning run (and the baseball cap too, while we’re at it.). When the sun sets, its time to wear the Big Girl Shoes.



 For your city break night look, depending on your destination, a cocktail dress or a dressy pair of jeans paired with a blazer, heels, and killer accessories may be appropriate. No matter the climate, this really depends on what city you are in. But it is always a better feeling to be a bit overdressed than under. You can always take your jacket off or carry flats in your handbag if you’re worried. But once you have made the sweatpants commitment….well.

And yes, you may bring your hair straightener, faux lashes, and the like on a city break. The Highland Fashionista personally does not have the patience to use a hair straightener, but she has seen firsthand the magic that they can bring, and therefore concedes that it may be an essential item in a lot of suitcases. Just for God’s sake don’t burn the place down.

The Cruise.  Grab the big suitcase for this one Real Gals. All bets are off! This is the one opportunity that you may have this season to put all of those luxury purchases that don’t get a lot of play-time on display. Though there seem to be an increasing number of casual cruise lines out there, traditionally, there are two formal nights on board a cruise line on a week-long cruise. Go nuts. Tastefully nuts, though, of course, not Bai Ling topless-photo-opportunity-nuts. The Highland Fashionista likes to put one full-length gown and one shorter, slightly less dressy one in her bag in anticipation of these formal nights.

Zac Posen


Again, depending on where you are cruising to, you will need to count the days (or nights) remaining (after your formal nights)  that you will need an outfit and pack accordingly. Like with the beach holiday, choose things that are multifunctional and can go from day to night. I tend to favour shift dresses at night, as they are easy to wear, take up little space,  look good with a tan, and are a great way to showcase killer shoes.

Diane Von Furstenburg

Manolo Blahnik

Other necessary items: bathing suits (unless it is an Alaska cruise), cover-ups that multitask (again, no wet, shirtless, soggy bums in the Lido buffet, please! People are eating!), and your most adventurous footwear! You are in a controlled environment! No cabs, no subway grates! Limited walking distance and elevators everywhere! Yes, the ship may move (it’s a ship), but think of it as a challenge. You will get good at it. And of course, bring as many of your favorite accessories as you can handle.  The beauty of the cruise is, you can call upon the aforementioned guidelines of beach holidays and city breaks for your various ports of call, and only have to unpack once!

So whether you are just heading out for some weekend shopping, a city-break getaway, or a few weeks in a far-flung locale, if you find yourself staring helplessly into your closet of stuff before your next trip, remember these small tips. These are, after all,  the clothing staples that have seen the Highland Fashionista through many an exotic locale.  And, of course, Cleveland too. 


  1. Hey, I want to know about all the twee stuff in your closet, and maybe a post about why we even have that stuff at all. What's it for? Easter?

    1. I think every few seasons, I get tricked into thinking that if I balance something saccharine like a floral prairie skirt with my motorcycle jacket, it will even itself out. But at the end of the day, all it really means is I now own a floral prairie skirt that isn't really me, and just sort of barely works, motorcycle jacket notwithstanding. With age, I get better at resisting the urge to go there as I know these trends don't suit.

  2. Please, please tell me where I can get that Guess peacoat?

    1. I got my Guess pea coat several years ago at Macy's in upstate NY. They probably have similar styles available, as it is a classic style. H&M has some good versions this year as well.


Post a Comment

Talk to me...

Popular Posts