Skip to content

Ask Jess: Starting a capsule wardrobe, Best Weekend Trip Destinations, and More!

ask jess

Wearing Everlane shirt dressSimilar straw hat and J.Crew bikini. See my see my full Amalfi Coast travel guide in this post

Happy Wednesday guys! I am SOO excited because Shaheen is visiting me this week!  She got here last night and will be staying with me tonight as well–we had such a fun girls dinner with Kelly and Blair at SABBIA (it’s Eataly’s newest restaurant and it is SO CUTE. You can even reserve their cabana table which is perfect for girl’s dinners!)

Anyway, excited to answer 5 more reader questions in today’s Ask Jess post! Let’s jump in…

Do you have any tips on starting your own capsule wardrobe? 

Yes! Take out your entire closet, go through every item, and get rid of anything you haven’t worn in a year or anything you don’t absolutely love. Ask yourself “should I keep this?” and if your answer isn’t automatically an emphatic YES then it goes in the donate bin. No wavering. Be ruthless about what you get rid of. Only in a handful of cases was I later like “aw man, I wish I still had that”. Also, that really only applied to something I wanted for a costume ?

After you do this, take inventory of your wardrobe. What are the “holes” that are missing? Then use that to curate the items that you really need (this way you don’t end up with the same things over and over, like we always do!)

Additionally, for every item that you keep or buy, you need to be able to wear it several ways (like, at LEAST three) for different occasions. You don’t want something taking up space in your closet that isn’t really versatile.

One thing to remember (in life, not just for capsule wardrobes) is that you don’t need to focus on trends. I’ve been getting so many questions on trends lately and honestly–who cares!? Wear what you love! I pay no attention to trends (unless I see one that I genuinely love. But I don’t ever buy something just because it’s “in”).

If you want to know a secret…

I honestly have no interest in fashion. I think most of it is ridiculous (Like, chunky sneakers? Are you freaking kidding me?) and so much of it makes people feel inadequate just because they aren’t wearing  the “latest thing.” Furthermore, I just like clothes and the fact that style is means of self expression that has the power to make you feel really amazing.

Wear what makes YOU feel confident and beautiful, and forget about everything else!

Do you have any kind of wedding planning timeline or things you wish you had known?

Hmmm. Honestly my #1 biggest piece of advice is to hire a wedding planner. I could have NOT done any portion of the wedding planning process without Becky (If you’re getting married in Oregon you MUST hire her!!) She handled the timelines and made sure I was making the decisions I needed at the appropriate time.

In terms of things I wish I’d known…just that people don’t really notice any of the little things you obsess over–you know, the little Pinteresty details you think are so important, the favors, how your napkins are folded, what kind of flatware you’re using, etc. I knew this going in (I’m like the anti-bride) and I STILL found myself obsessing over details that didn’t matter. It’s easy to get wrapped up in it and you just need to make yourself take a step back and be like “oh yeah, I forgot NOBODY CARES ?.”

All your guests care about is that their is that they’re fed something, their drinks are flowing, there is great music, and most importantly–that the bride and groom are happy, in love, and having the best time. And if they care about anything else, they shouldn’t be invited to your wedding anyway! You do you! Put on the blinders and focus on bringing a day to life that really feels like the two of you.

Any ideas for couples or girls trips?

I just wrote a post on Weekend Getaways from Chicago for those of you guys who are local! Neal and I went to Miami this past winter for a weekend (I surprised him for his 30th birthday) and we LOVEDDD it! Read my Miami weekend recap here. We also had SO much fun in Toronto (we were there for a wedding so we didn’t have a ton of free time so I won’t be doing a guide on that) and would definitely recommend it for couples or girls trips–as well as Montreal–see my guide here.

What “little things” do you and Neal do to make each other feel special?

If you don’t know what The Five Love Languages are–I would HIGHLY recommend reading it (and/or just taking their quick little quiz online!) Knowing your partner’s love language is REALLY important, and that’s how you know what KIND of little things to do that make each other feel special. Some people are a mix (I’m kind of an even split between “gifts” and “acts of service” with “quality time” mixed in there, and some people are very dominant with one or two (Neal’s is very much “Words of affirmation.”). Also, there are Love Languages books for children, teenagers, single adults, and more. You can find them all on Amazon.

Neal will surprise me with little things like beautiful flowers, or buy me two types of blue gatorade because sometimes I like light blue or sometimes I like dark blue and he wanted me to have both choices. I will buy him little cards and write him notes of love and appreciation when I feel like he needs a pick me up or just because. Also, we both prioritize spending time together, because Quality Time is the one love language we both rank high on the list.

How do you become comfortable in front of the camera?

A LOT of practice. Just do it. And have a drink or two beforehand if you need to? It’s a piece of cake once you’ve gotten used to it!

Granted, I’ve always been “a ham” in front of the camera, as my mother would say, so the worst part for me was just getting used to taking photos on the street with people staring at me, but it doesn’t phase me anymore. People just think you’re doing a photoshoot of some kind–I doubt they think twice about it. (And if they do–who cares?)

It all boils down to practice. The more you do something, the more natural it becomes!

Read more “Ask Jess” posts right here